In one line
Megan Labadie, a top enterprise seller of ESG regulatory-compliance software (at a company she asked not to name), closed at a roughly 49% win rate on ~18-month deals by being "the everyman" — teaching, tailoring and taking control of complex deals — and by winning them internally through champions and subject-matter experts, on Sales Success Stories with Scott Ingram.
Who is Megan Labadie?
Megan Labadie is one of the top individual-contributor sellers at an ESG (environmental, social & governance) regulatory-compliance software company — a firm that gave her permission to appear but did not want to be named. A self-described "intentional individual contributor" and money-motivated New Yorker now based in Tampa, she has spent roughly 15 years in tech sales since graduating in 2008. Her path ran from leasing apartments at Post Properties in Atlanta, to cutting her teeth in full-cycle payroll sales at Paycom, to enterprise software including a stint at Oracle (in the Oracle Marketing Cloud / Eloqua era). She is now in her second tenure at her current employer, selling ESG compliance software into the largest prospects and carrying an ~18-month enterprise sales cycle. She was connected to the show by past guest Samantha "Sam" Price.
Key questions answered
What are the top things behind Megan Labadie's consistent sales success? Per Megan Labadie, on Sales Success Stories, three factors matter most: a genuine willingness to both give and receive feedback among teammates and subject-matter experts; welcoming tough conversations ("the more awkward the conversation is, the more you're learning from it"); and only working for a boss she genuinely respects and finds smarter than herself. 0:01:56
How do you handle a tough negotiation like a stalled MSA? Per Megan Labadie, in a Master Service Agreement negotiation you're appeasing three parties — the business on a timeline, procurement worried about KPIs, and legal that wants it done "our way or the highway" — and as the seller you sometimes have to push back honestly ("I just don't think it's realistic we can get this done on this timeframe") without losing sight of your own mental status. 0:05:14
How do you vet a sales manager before you take a job? Per Megan Labadie, treat it like dating and do real due diligence: ask "who on your team can I talk to?" during the interview, because peers are often more transparent than they should be, and trust your gut when a role feels like a miss. Scott Ingram adds his own hack — find someone who used to work for that leader but no longer does, and ask the binary question "would you work for them again?" (resources at top1.fm/dd). 0:13:14
How does Megan Labadie sell complex ESG software to non-experts? Per Megan Labadie, she sells as "the everyman": she is not the ESG expert — the buyer is — but she is the expert in making their data more efficient, consistent and full of integrity. She uses "teach, tailor, take control," a simple mountain visual, and deliberately widens the pain so the CIO, chief accounting officer and internal-audit teams all see it as the biggest problem, not just the sustainability team. 0:19:13
How does Megan Labadie quantify her results? Per Megan Labadie, she is having an incredible year with roughly a 49% close rate ("which is bonkers") on deals that take about 18 months to close. She grows deal size by expanding the number of stakeholders and tying more revenue to the regulatory problem, and she protects her time by asking the uncomfortable qualifying questions early — is this budgeted or exploratory, is IT involved, is procurement involved. 0:19:21
How do you win a complex enterprise deal internally? Per Megan Labadie, her biggest ally is a happy existing customer inside the target account: she validates that champion, brings them into demos to speak to how they use the tool, and leans on subject-matter experts (including a Europe-based team for European ESG rules) over executive-to-executive "kikis." She estimates the time split on a big deal is at least 50/50 internal-versus-client, and her favorite call is the one-day-after-demo debrief with the champion. 1:03:25
What's Megan Labadie's challenge for sellers who want to improve? Per Megan Labadie, her closing challenge on Sales Success Stories is to record yourself in a meeting and then listen back — watch the faces, hear how you come across and how many times you stumble over words — and to sit in on other people's calls, because "we are our worst critics" and it is the fastest way to actually get better. 1:36:37
Frameworks & concepts
- "The everyman" selling style — deliberately not posing as the subject-matter expert; instead making complex ESG problems simple and relatable so every stakeholder in the room sees how the problem impacts them.
- Teach, tailor, take control — Megan's borrowed-from-Challenger framing for educating the buyer, tailoring the message, and controlling the narrative of a complex deal.
- Widening the pain — expanding a problem so it's not owned only by the environmental/sustainability team but felt by the CIO, chief accounting officer and internal audit, because that's where budget and urgency come from.
- General-to-specific discovery — ask the broadest questions first ("tell me about your process") so the prospect steers you to what matters most to them, then drill into second- and third-level questions.
- Winning internally / wielding your organization — on complex deals the majority of the work is internal (~50/50 or more); the seller orchestrates champions, solution engineers, value-management and Europe-based experts and then gives them credit ("their flowers") to keep those doors open.
- Champion-led demos and internal references — the best reference lives inside the buyer's own company; bring your happy existing customer into demos, and when they demo the product themselves, "they've done the selling and I'm just here to facilitate."
- The intentional individual contributor — a shared Scott/Megan philosophy: leading from the field, elevating peers and mentoring "at scale" without ever taking a management title.
- Learn, teach, learn — the DeJuan Brown philosophy Scott cites and Megan endorses: learn something, reinforce it by teaching it to someone else, then learn again through their application.
- The breakup email — when a deal goes quiet, a "sounds like you've moved on to other priorities" note has, in Megan's experience, roughly a 50% chance of drawing a real response.
Notable claims
- Per Megan Labadie, she is closing at roughly a 49% win rate on enterprise ESG deals that take about 18 months to close.
- She has spent about 15 years in tech sales, essentially her whole career since graduating in 2008, and is in her second tenure at her current employer — a company she first tried to sell this ESG (then called "corporate social responsibility") software with about 10 years ago, when buyers had "zero or laughable amounts of budget."
- On a big deal, she estimates the split is at least 50/50 internal vs. client-facing time, often more on the internal side — counterintuitively, the more complex the deal, the more time is spent inside her own organization.
- She actively qualifies toward friction: if legal, procurement and IT are involved, the deal is serious ("if IT is not involved, I'm in trouble").
- Deal research she swears by: reading a prospect's proxy statement for ESG mentions (she once found a company tying executive compensation to ESG goals) and name-dropping the company's actual benchmarking peers who already use her product — "it's game over, it's trust."
- A "breakup email" to a silent prospect gets a response roughly 50% of the time.
- She once turned around a churn-risk account by proving, with her customer success manager, that the unhappy customer had spent only 1.5 hours in the system and skipped the suggested trainings — then re-engaged them on the condition they complete the trainings.
Companies, tools & books mentioned
Companies & organizations: Oracle, Oracle Marketing Cloud, Eloqua, Workfront (Alex Shootman; later acquired by Adobe), Adobe, Paycom, Post Properties, ADP, Deloitte, University of Tampa, University of Maryland, Delta Sigma Pi. (Megan's current ESG-software employer is intentionally unnamed. Oracle's Safra Catz is referenced in Scott's Eloqua/Oracle negotiation story.)
Tools: Salesforce, SalesLoft, Consensus (interactive demo platform), Zoom, Slack, Evernote, the Notes app, physical notebooks, AI note-takers.
Books & methodologies: The Challenger Sale, Never Split the Difference, Franklin Covey sales training.
Regulation: ESG reporting; the EU's CSRD (Corporate Sustainability Reporting Directive); emerging California disclosure mandates.
People & community cross-links: Samantha "Sam" Price (who connected Megan to the show, episode 178), Jack Wilson (Sales Success Society; episodes 57 & 166), DeJuan Brown (episode 6, origin of "learn, teach, learn").
Connect with Megan Labadie: LinkedIn.
Quotes
"So, the more awkward the conversation is, the more you're learning from it. So, I've learned that although they're not the most fun calls to get on, they are the most impactful. They're the ones that you learn from." — Megan Labadie 0:01:56
"I am not an expert in ESG. You're an expert in ESG, but I'm an expert in how I can make you more efficient and consistent and bring integrity to your data. That's my area of expertise." — Megan Labadie 0:19:13
"The only thing you have to do is uncover what their pain is. And the only way you're gonna do that is by listening to what they're saying." — Megan Labadie 0:39:41
"The ultimate way to demonstrate expertise isn't what you say, it's what you ask." — Scott Ingram 0:41:11
"Your best reference, by the way, is sitting in your own organization. Someone who knows how you guys operate." — Megan Labadie 1:03:25
"Learning when you can absolutely own what you've done wrong, but also recognize that you don't have to own up to things that you haven't failed at. Some people might think that's crazy, but you can't let people walk all over you." — Megan Labadie 1:12:34
"Just be bold, be bold. You're gonna fail. You'll have things that don't work out, but you'll be surprised by how many doors open up by just asking what you want." — Megan Labadie 1:19:42
"We think that we are the star of their show. We're not. We're a very small aspect of what they're working on day to day." — Megan Labadie 1:28:57
0:00 Scott Ingram: You're probably listening to this podcast to learn from the top 1%. However, there is no silver bullet. The top 1% get there by mastering all the fundamentals and intentionally working on specific areas of improvement to always sharpen the sword. The rest of this episode is brought to you completely uninterrupted thanks to The Sales Collective. Their secret sauce is helping you figure out the exact areas you need to improve compared to the top 1% using a mindset and skill-based assessment. They then offer training on those exact areas. They make figuring this out and developing where you need it easy. Head over to thesalescollective.com to learn more, or reach out to David Weiss on LinkedIn and let him know that Scott Ingram sent you. You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help help you improve. To learn more, visit us at top1.fm. Here's your host, Scott Ingram. Today on the Sales Success Stories podcast, my guest is Megan Labadie. Megan is one of the top salespeople at a regulatory compliance software company that gave her permission to come on the show but didn't want to be named. Kind of funny, but the important thing is that Megan is here. Welcome to the show.
1:28 Megan Labadie: Thanks for having me, Scott. Super excited for this.
1:31 Scott Ingram: I am so looking forward to this conversation. And I also want to give a quick shout out to Sam Price, who may or may not work at this same company for getting us connected. So you guys can look everybody up on LinkedIn and connect the dots. Megan, let's start like we always do, immediate value before we get into all the context and all the stuff. What are the top 3 things that you believe have contributed the most to your consistent success in sales?
1:56 Megan Labadie: Yeah, and such a great question, and I loved listening to your other recordings and hearing what people said. So I thought a lot about it, and I think the first thing that can be really hard, especially depending on how long you've been with a company, is your willingness to both give and receive feedback. I've been in tech sales now for 15 years, basically been my whole career, so it's important that you still recognize that You're going to have new teammates along the way with different perspectives, right? Sam is newer to our organization and she comes with such a wealth of information, just a different way of looking at things. We're working with subject matter experts, solution engineers. In this environment where you've got so many people coming together, you really need to make sure that you're all elevating each other and just really being open to the fact that people are going to give you feedback. And if they're not, you need to ask for it. And also being comfortable to share it to make sure that, you know, in a respectful way, everyone can be brought to the next level together. So I'd say that's my first one. The second one is welcoming tough conversations. We get these often in our careers, right? And they're going to be around different topics. Maybe someone's not happy with an implementation or one reason or another, or you're getting on with a really tough procurement person. It's never fun to have those types of conversations, but when you do get through them, when you just hit them head on, it makes you so much more well-equipped to handle those situations in the future. So, the more awkward the conversation is, the more you're learning from it. So, I've learned that although they're not the most fun calls to get on, they are the most impactful. They're the ones that you learn from. You make diamonds with pressure. Is that the saying? I'm not really sure.
3:41 Scott Ingram: Yeah, that's how it works.
3:43 Megan Labadie: Yeah, okay, perfect. And then the third one is, and this is something I've learned as I've sort of matured in my career, is that I have to work for somebody that I feel is smarter than me. When I am thinking of taking on a new role, it's like, okay, what's my salary? What's my OTE? And is this someone who I feel like I would have respect for every day, look up to? The company I'm at now, I've actually been there twice in my career. I've worked for some of the most amazing people. It's a Midwest company, so just like good people at the heart. I say that as a very humble New Yorker. We do love those Midwest folk. But I think when you've got someone who you feel like, wow, they're smarter than me, or not smarter, but like they just think about things differently than I do, it's again, just another great way to elevate yourself, to invest in your growth. All those good things really comes from having a boss that you genuinely respect.
4:40 Scott Ingram: Such good points. I want to dig a little bit deeper into the last 2 in particular, especially now the tough conversations thing. We're in the middle of Q4. And this is the time that what you made me think of initially is, you know, that spidey sense that you're getting about where you're getting paranoid where this deal might go sideways. And rather than hiding from that, just, okay, I just need to ask. I'm curious about the examples that come to mind for you. How do you think about that? What are some of those most powerful conversations you have to have? Maybe the most recent one.
5:14 Megan Labadie: Yeah, yeah, I've got one I'm in the thick of right now, and it's an MSA negotiation, which is never easy. It's always lengthy. So working with someone we don't already do business with is just tough. And the nature of MSAs is they take a really long time to negotiate, and you've got 3 different parties that you're appeasing. You've got the business who's working on a timeline, you've got procurement who is worried about getting the deal done but also worrying about their KPIs, and then you've got legal folks who are just worried about, I don't care how long it takes, it has to get done our way or the highway. And sometimes you've got 2 companies that just don't agree on those things, and it just makes it so tough. And as the seller, you have to sort of appease all of those folks without losing sight of, first and foremost, your mental status. At some point, you probably have to have a tough conversation like, listen, I just don't think it's realistic that we can get this done on this timeframe. We're doing everything we can, but maybe it's not the right fit for us. So sometimes you do have to push back a little bit and not be afraid of that. If you've been selected as a vendor and you have confidence in your product, and I understand processes are processes, especially in large organizations, but these things take time. There's challenges, there's bumps, and especially in Q4, it's at least time when people are hopefully looking to just move things along and get on about their holidays. So yeah, I'm feeling that for sure in a couple different places right now.
6:43 Scott Ingram: Yeah, that reminds me of a story of my own, one that I don't think I've ever shared this on the show.
6:51 Megan Labadie: Ooh, excited.
6:52 Scott Ingram: You know what? I think I'll name some of the names. I won't name all of the names because it's long enough distance and everything else. I don't think there's any issue, but this involves an organization that we both worked for at one point. I was negotiating a deal between Oracle and a very large, probably Fortune 20 scale company. And you've worked at Oracle, you understand this part. Oracle's sort of legal stance is that is our agreement and it doesn't change. There is no budge in the way that that works, right? So there was always a lot of expectation setting around, look, you can ask for stuff, but you're basically wasting your time. Well, the organization that I was selling to was very similar in their philosophy. So I had these 2 very large organizations that basically as a rule did not budge. And the really funny thing is they both did billions of dollars with business between each other and hated each other. So that's the landscape I go into. There's more leading up to this that's really fun. I should do a whole deep dive on this at some point, 'cause it's one of the craziest stories of my career. Long story short, I work with the ultimate champion inside this organization and we figure out how to get both of our sides to kind of budge and bend the rules and make this work so that we can get this deal done because Eloqua was the platform and this guy had built his career on Eloqua. They needed this platform and the organization was going to walk away. Somehow or other, I get this deal done. Flash forward to, at the time, Alex Shootman, he was like the GM of the Marketing Cloud at this point, right? So we'd been acquired into Oracle. He'd been kind of elevated into this position to run this. Portfolio of different marketing platforms that they had. And he was here in Austin with me. He has sort of a going away party. It's time for him to leave. He's going to go become… I don't think we knew this at the time, but he was going to become the CEO of Workfront, who's now been acquired by Adobe. Anyway, he pulls me aside in this going away party and says, Scott, I will never forget what you did on that deal because that was the first deal-related conversation I ever had with Safra Catz. Safra is currently Oracle's co-CEO. At the time she was their CFO. So he's having a most senior level executive relationship internally about this. And he says, yeah, when Safra and I talked about that deal, we wrote it off. It was not possible. He's like, I don't know how you did it, but you literally pulled off the impossible. Anyway, I took way too much time. This is supposed to be about all the upfront value, but you triggered that story and that flashback and Yeah, negotiating MSA sucks.
9:45 Megan Labadie: Oh, it's so funny because I have almost an identical story also while with Oracle, and I won't name the customer, but I wonder if it's the same one, but we did not get it done. On the flip side, we kept feeling like we're coming back and our legal team's doing so much, and their legal team was like, it's just not enough. You guys are not moving the needle. It was so frustrating. One of those massive career deals that ultimately did not get done because…
10:11 Scott Ingram: Yeah.
10:11 Megan Labadie: Of legal disagreements. So it happens.
10:13 Scott Ingram: We'll compare notes after we finish the recording, which is my favorite part of being the host of this podcast. I get to get the insider information. Let's also talk about… I love this last point about only working with people you believe in. I mean, this is a little bit anecdotal, but it is very directionally correct. I only interview number one, top 1% individual contributors on this show, and I'm pretty convinced that There have been almost no examples of people who have gotten into that position despite their boss. If you don't have a great leader that's supporting you overcoming that on top of all the other things that you have to overcome in just day-to-day sales life, it's a mountain too far. I love that you are so mindful about that. How are you qualifying that? How are you figuring out, hey, this is a person that can be that person for me?
11:07 Megan Labadie: Yeah, I don't know if it's fortunately or unfortunately one of those you just kind of got to learn by failing. I've had some terrible leaders and bosses, and I've had some incredible ones. And I think the hard thing too is often when you have a really good boss, inevitably they're going to get promoted because they deserve to.
11:28 Scott Ingram: So that's my next question. What do you do when they're no longer your boss?
11:32 Megan Labadie: Yeah, I've had that situation too. I actually had an amazing manager that came from Eloqua. And then he ended up also getting promoted and getting someone who I just didn't jive with. So I think again, it just takes time to understand having bad bosses and having great bosses, like what works for you. I think personality fit is number one, but then also not being afraid of somebody who's different from you. I had a switch in managers a little over a year ago, and it was someone where I was just like, God, we're so different. I feel like I am very How can I make this as simple as possible for people? And he's someone who just thinks about things so deeply and consultative and again, just so intelligent that I was like, we're either gonna clash or hopefully best case scenario, we are just the perfect complements to each other. And luckily that's how it worked out. And he has also since been promoted, which was a killer, but well deserved and hopefully will make an even bigger impact at the company we're at. But yeah, I think it just. And sometimes you have no choice and things change and you get stuck with people. And I think too, it's your manager, especially in sales, is someone you end up spending a lot of time with, a lot of late night phone calls and strategy sessions. And you actively have to work on those relationships and making sure that you can get on the same page about how you're thinking through things. If you're not willing to put in that time, it's not going to be a fun environment to work in.
12:59 Scott Ingram: Yeah. Again, I want to lean into that a little bit more, just the 2 points. How are you Just testing that it is going to be the right person. And maybe it was just kind of a leap of faith that you had to take with somebody who was very different stylistically. What do you do when they do change?
13:14 Megan Labadie: Yeah, I guess a little bit of a leap of faith when you're going to a net new company. It's kind of like dating. People are one way when you are just getting into the mix of things and during an interview process, everything is roses. And then sometimes you get into a situation where it's like, oh, maybe that wasn't the case. So you do have to Put a little bit of trust in that. I think too, we have a lot of gut instincts. If everything feels like a fit, but this is a miss, or also I would suggest if you're feeling a little bit unsure, just say like, hey, who on your team can I talk to? Because very often we don't get to interview with peers or talk about their day-to-day, and their perspective is really important. And a lot of times people will be probably far more transparent than they should be. I think really doing your due diligence on that side is important, however you want to get that done. Again, this has come up a lot. We have a pretty fast-growing company here. We do a lot of promotion within, which is a wonderful thing, but it does come with a lot of change and turnover in that department. I'm always someone, and this is, gosh, going to seem so pushy, but I'm always like, well, who's interested in the role? Who can I talk to to convince them that this is the right move? Because I really love being an individual contributor. Management is not something for me. So I think oftentimes people will look at me for that and I'm like, I don't know. I really like where I'm at. So I try to Also do a little bit of selling internally on the role to other people who I would like to work for. So it's a bit selfish, but also in the grand scheme of things, if I'm happy, I will perform.
14:47 Scott Ingram: We are so similar. I also call myself an intentional individual contributor. The boss before my current boss, I recruited into the organization to be my boss. We had this role available and I didn't want to leave anything to chance. I'm like, let me put somebody in that I know I can work really well with. And then in this most recent iteration, they came to me and said, we're just checking, Scott, because we know you. You don't want to be the VP of sales, right? I'm like, nope, not it. That guy. Right? So that matters a lot. The other thing is I am a freak about the due diligence side. In fact, I have put together a whole set of resources on this topic. If you go to top1.fm/dd for due diligence, I've pulled together a ton of stuff. My hack The easiest way I have found to validate a leader that you're going to be working for is find somebody who's worked for them before that does not work for them now. And you can boil this down to one single conversation. If you had the opportunity to work for this person again, would you or wouldn't you? It tells you everything you need to know. You can ask follow-up questions from there, but it's kind of a binary answer. If they would work for them again, that's a really good sign. If not, giant red flag. I try to do that external to the organization because sometimes, I mean, again, you do get a lot of honesty as you described it, but there's also some political risk for them in that. And you might not be getting the whole truth and nothing but the truth in that situation.
16:14 Megan Labadie: That's great advice. Yeah.
16:16 Scott Ingram: Let's contextualize a little bit as much as we can. So, talk about your role, kind of who you're selling to and how you've gotten to the top of your group there. Yes.
16:26 Megan Labadie: We're not verticalized or anything like that. We are kind of split into revenue bands. So, I am selling into our largest prospects for an ESG software. So it's very much relevant and top of mind right now. It's funny because this is my second time around in this space at the same company. So we tried to do this 10 years ago, back when everyone called ESG corporate social responsibility, if anyone remembers that. And everyone had all the same problems they have today, but zero or laughable amounts of budget to solve those problems. No one really cared. So now there's regulation, there's a lot of things that are coming with that. And I think one of the things that I've done that's made me successful in this particular role is, again, I'll say it like I always say, that my sales style is I am the everyman. I really try to not dumb things down, but I try to bring everyone to the same level because subject matter experts, they get it. And I always say, like, I am not an expert in ESG. You're an expert in ESG, but I'm an expert in how I can make you more efficient and consistent and bring integrity to your data, right? That's my area of expertise. Expertise. But often, as the conversations get more serious, more stakeholders are getting involved. And now you've got people that are from the outside looking in, not really understanding the pain, the requirements, and what's at stake. So, it's very much that teach, tailor, take control. So, we've got like a couple great visuals, and I've heard it delivered so many different ways, but I am just so basic about it. Like, hey, this is a mountain we're looking at. If you're starting at the bottom, these are the things that you'll need to accomplish. And this is why you can't do it without tech. It is such a big lift. It has penalties that are associated with it. It's now regulatory. We've got a lot of other countries, and even here in the US, we've got California making mandates. This is something that is growing as far as the regulations, but even if it doesn't impact somebody on the regulatory side, it's going to impact them because their peers are going to start doing this. Everyone's going to have to uplevel. I think I've just really leaned into how can I make this message and these pains as relevant to as many stakeholders into the organization? Because it is hard for these folks to get budget and they've got a lot of competing priorities. So how do I make my problem seem like the biggest problem? Because frankly, I genuinely think it is, but really making all the stakeholders, not just taking that to our environmental and sustainability folks, but how do I get the CIO and the chief accounting officer and the internal audit teams to all be like, yeah, this is a huge problem. I'd say that's probably what I lean into the most.
19:13 Scott Ingram: Very nice. Very nice. Can you quantify and kind of put your results in perspective for us? What does it take to get to the top of your team?
19:21 Megan Labadie: I'm having an incredible year, which is super nice. It's funny because we just did our annual reviews and I had like a 49% close rate, which is bonkers. And our sales cycles take a really long time to close. Probably 18 months, some being shorter, some being longer, but almost always it takes a year. Again, the bigger the problem, the more revenue you can tie to that problem. So, when this was just, hey, people are working on a voluntary report here, and now it's going to regulations, and now it's like, we've got hundreds of entities, and those entities are impacted by this, that really helps to grow these deal sizes. So, again, going back to that, expanding how many stakeholders are involved, Also bringing in our champions. We've got great customers that really love our platform. Platform's a big play across the board. CIOs, that's something they care about. We want less technologies versus more. Leveraging all those things has helped me get up my deal size, has helped my close rates. I think the other thing that also comes with some time in the saddle is I've gotten pretty good at knowing where to spend my time, knowing what deals are not going to pan out or that are just not worth spending time on right now, asking those comfortable questions that sometimes people don't want to ask. Like, is this a budgeted project or is this just exploratory? Is IT involved? Is procurement involved? How serious is this deal? And then realistically spending your time where it should be versus just exploring everything because you're excited to have those opportunities moving along.
20:53 Scott Ingram: Nice. Nice. In your case, I'm guessing you're qualifying around, you actually want legal and procurement to be involved because that means they're serious, not like, oh, you're just kicking tires. Yeah.
21:02 Megan Labadie: Heck yeah. I love that. Like, if IT is not involved, I'm in trouble.
21:07 Scott Ingram: Got it. Got it.
21:08 Megan Labadie: Brilliant.
21:09 Scott Ingram: Let's go all the way back to the beginning. I want to hear your origin story. How did you get into sales in the first place? Yeah.
21:16 Megan Labadie: So my first job out of college was leasing apartments. I got a job for a company called Post Properties at the time, which has since been acquired, but they were based in Atlanta and it was like the softest sales job. People come to you, they walk into the office and I loved it. It, it's really interesting when you are leasing apartments because you see people in all different states of life. You've got a boyfriend and girlfriend who are moving in together for the first time, or you've got somebody who's going through a divorce and having to navigate that, or someone who's moving to a city for the first time. So I think what that got me really comfortable with was having lots of different conversations with tons of different people in different situations. And there are aspects of sales to it. People do come to you, but there's follow-up. So that was sort of my first dabble into sales. And I did very well there. I loved that company, but at the end of the day, I was like, we all get paid the same, and maybe I feel like I should be a little bit more elevated. So I ended up interviewing for a job at a payroll company, one called Paycom. And if anyone's ever sold payroll, like, that is not an easy gig. That is a great place to, like, cut your teeth in sales experience. So I remember the interview process. We had to go in for, like, a 4-hour calling blitz and cold call people to try to get them to set meetings. And the goal of the interview… this was the second part of the interview… but was to set 3 meetings. I set 1 meeting, which was very difficult. It was like 4 hours of just pain. And I was like, oh God, this is not what I want to do. This is so miserable. And I met with the hiring manager after and she's like, yeah, what'd you think? I was like, yeah, I mean, I really enjoy everyone here. It's unfortunate I didn't get my 3 meetings. But thank you so much for your time. And she's like, no, no, wait, we really like to stay on. So I kind of took a risk. And like I said, that was my first step into, this is real sales where I am cold calling, I am demoing, I am giving proposals, ran payrolls with people. I owe a lot of my career to that company. They invested a lot into people and very much that apparently I'm someone who, when you dangle money, I was like, oh, this is amazing. And in that role, if things were bad, they were bad. But if they were good, they were so good. That was my first real sales gig. And from there I've bounced around to a couple of different tech sales companies.
23:34 Scott Ingram: Nice. I took a sort of similar path. So my first traditional sales job was with ADP. And honestly, I recommend this to so many people. I mean, in tech sales these days, the path really seems to be so much about you're an SDR and then you're an AE and you kind of climb the ranks that way. I, for similar reasons, like the payroll play because it's full cycle. Because you're learning everything. They invest a lot in training and you learn business. You're building a real ROI based on very quantifiable things like, okay, cool, this is your labor force. It's literally your biggest expense item. There's very few companies where payroll isn't the biggest, most expensive thing that you have. So how are you dealing with that and all the regulatory stuff and everything else? I think it's an amazing space that is really overlooked as an entry into sales. And my next question is really related, knowing all that you know now and all the experiences you've had, if you were starting your sales career over today, what would you do? How would you approach it?
24:33 Megan Labadie: Oh gosh. Honestly, I agree with you. I feel like payroll sales, and I'm sure there's other careers like that, but having that full circle of all the things that you have to learn was so impactful. I learned so quickly. And then, I don't know, that's such a good question. I knew I could never go into medical sales, which I feel like was I graduated college in 2008, so like everybody wanted to be in medical sales, but I am queasy, can't handle blood, none of that. So I sort of knew I had to figure out another path. And then tech is the new darling of the industry, so it's nice to be there. I like that it was more than just, like you said, cold calling and setting meetings all day long. That was clearly my least favorite part, and I think everyone's least favorite part. Nobody wants to cold call and have to walk away crying to the bathroom because some controller at a 30-employee company was rude to you, right? But it sort of is what it is. Doesn't have to be payroll, but something where you can get all the aspects of sales so you can really see what it's like. Because I'm sure a lot of people go out and get these BDR jobs, and even at Oracle, like, they only wanted to hire BDRs from top colleges and universities, Ivy League and things like that. And I'm like, I don't know, are these the people that really shine in sales? I went to the University of Tampa, which is hardly known for its academia. Oh, I love UT, please, University Tampa, but getting that, if you're hiring people and they're only just cold calling, I'm sure a lot of people are walking away from sales because they're like, I just don't like this. So having a little bit of everything is really a good way to round out the whole experience and see what you do like. Love that.
26:07 Scott Ingram: Love that. It's funny. I'm thinking about it. I did this so long ago that SaaS wasn't really a thing. And it was an interesting realization of, you know what, ADP is SaaS. I'm literally selling a subscription product. It is technology. It was such an interesting thing because they don't really position them. I mean, maybe they they do now, but they really didn't position it that way. But it is.
26:28 Megan Labadie: Agree. We've had such a similar path. It's really funny. But I remember interviewing for like my first job after that, and they were like, well, you don't have software experience. And I was like, I sell software. That's literally what I sell. Paycom's a cloud-based company. There was no on-premise software, anything like that. So I was like, no, that's exactly what I do. In that moment, I put 2 and 2 together. Before then, that's not really how I thought about Too funny, Megan.
26:52 Scott Ingram: What is your favorite sales story? Maybe it was a big one. Maybe it was a big loss. Maybe it was the painful lesson that has just taught you something that you have to carry forward.
27:02 Megan Labadie: Oh my God! This is such a hard question. I feel like the pressure's on to deliver a great story, but I will say probably in my first real sales job, and this is probably what just lit my fire to love sales. Getting commission checks is great, but getting like a big. Life-changing commission check is pretty nice. And I remember my first big one, but it was 5 figures. It was juicy for someone who was, I think it was like 24 or 25 at the time. And it was here in Tampa where I live. We've got like a big restaurant group and they were spinning off another set of restaurants. So in payroll, the number of employees is like how you get your deal size up. So it was like a juicy one and it was one of those that that it was competitive, it had every aspect of highs and lows and the negotiations and learning so much and really feeling like I grew from that opportunity. And then getting to reap that benefit was incredible. And again, being at an age where that money was unfathomable to me, it felt so good. So I'd say that's probably the one that sticks out the most because it really motivates you. I actually helped bring on a client of mine, somebody I sold to about a year ago came and joined our organization. And that's like a great testament to our product as well. But she came to sell for us and she's never sold before. And I remember her being like, oh wait, when she closed her first deal, it was kind of small. And anyway, I was joking with her and the account manager that she works with. And he was just like, soon you'll get a check like this and you won't even care about it. Not that it's all about the money, but I mean, it's such a great feeling and getting to that point where you can reap the benefits of the late nights and the stressful calls and paying for your Xanax subscription, I suppose. So, so it's nice to get that reward. And I obviously, there's a lot of careers out there where people have to work really hard and you don't really get the financial benefit from it. So it's nice. It's what definitely keeps me motivated. Yeah, my bosses all know that.
29:03 Scott Ingram: Yeah, well, let's keep talking about that. I mean, is that the core of kind of your motivation and drive? And has that evolved over time at Yes, 100%.
29:12 Megan Labadie: I am money motivated all day, every day. I'm not here for fun. I do love the company I work for. I'm so grateful to be here, and I feel like they incentivize us the right way, which is great. I do think that probably earlier on in my career, I was very much like, I went to business school and I was in Delta Sigma Pi, which is like a business fraternity. I was the president. I was so involved in everything, and I was like, I'm gonna go climb the corporate ladder and be an absolute boss. That's what motivated me, knowing that I could go up levels and levels and eventually reach the top was my goal. And then I managed a team for the first time, and I was like, oh my God, this is not for me. And I think a lot of people stay as an individual contributor their whole career, and there is nothing wrong with that. In your good years, you're going to make more than your bosses. Everybody knows that. So yeah, I think it's changed that now it's just like when you have a great earning year, your next goal becomes how do I beat that year?
30:14 Scott Ingram: Nice.
30:14 Megan Labadie: So yeah.
30:15 Scott Ingram: What are you most proud of? I mean, you've had a lot of success over the course of your career. What makes you the most proud?
30:21 Megan Labadie: I would say I am most proud of my relationships with my colleagues. I am someone I feel like people that are not on my direct team are picking up the phone, they call me, they ask me for advice. So to me, that's the symbol of, I want to know what you're doing. I want to know how you're doing it. I want to bounce an idea off of you. I trust you. Those are all the things I hear when someone picks up the phone and calls me and asks for advice. I'm very much a, like, what goes around comes around karma person. I have been at the top of my game. I have been at the bottom of the barrel. It's all cyclical. It all goes around and around, and I have always made sure that And even recruiters, when recruiters reach out to me, I'm probably the only person who responds to everyone to be like, hey, I'm not interested at this time, but please keep me in mind. And I know that they're also selling something and that there may be a time when I need to go back to those folks, which very much happened to me during COVID I was working for a small startup and all of a sudden I was back in everyone's inbox who had been blowing me up for years trying to get my next role. So yeah, I'm very proud of that, my ability to again, just be an ear for people, someone that they trust and that they look up to. So I'm proud of that.
31:36 Scott Ingram: I want to pull at this idea of, again, just kind of helping and pay it forward, because I think the perspective from a lot of people is I'm not going to get time with our number one seller. They're so busy, they're so money motivated, they have this big ego. Why is that wrong? How do you see it when folks reach out to you?
31:56 Megan Labadie: Yeah, again, I see it as a compliment. I also feel like I work for a public company. I have stocks in that company as well. When they do well, we all do well. It's important to really lean into those people, especially being a little bit more tenured on my specific team. Sometimes you're not comfortable going to your boss or someone who's more senior than you for help with things. And it's funny, I had a boss very early on in my career who just was someone who never answered the phone. And I always joke, like, he's the manager I learned the most from because I just had to figure things out, which is a very interesting way to think about it, but I was just left to figure things out. I've always made sure to try to take care of other people and elevate them as people have leaned into me, especially when I was newer in my career and young and just making mistakes and not doing things right and not understanding how I'm coming across to other people. I think too, when you're young, and you look young or you sound young. It's like, we need to elevate things because we can only control what we can control. If we can make sure to eliminate some of those concerns, which exist, they just do, we've got to do that. I'm really big into giving feedback and sharing my thoughts and opinions in a respectful way. And hey, well, why don't you demo that to me? Okay, let me show you how I would have done that. So I'm open to it. I love it. I feel like it's my little step into management without having to be a manager.
33:21 Scott Ingram: Yeah, there's 2 groups of people I want to talk to, and this whole intentional individual contributor theme, you're demonstrating one of the things that I think about a lot, which is I lead from the field. I don't need a title. I don't need people reporting from me, but that doesn't mean that I can't contribute and impact the organizations in bigger ways than just bringing in the dollars and bringing in the revenue. But for folks who are not at the top yet, like they're earlier in their career, they're new to the company or those things. It's just recognizing and understanding that people who are at the top almost always are happy to help. They're happy to pay it forward because we all had help in getting there. It's the reason this whole Sales Success Media thing works. The reason I get to have these interviews and talk to people for freaking hours about their stories. Is because of this. This is why we have such great presentations at the summit and people participating in the Sales Success Society is because of all this. That's the message for those folks. Don't be shy. Just ask. People are happy to help. If you are at the top, the challenge I have with this show is there's this level of humility. Megan, you did it with me. Sam connected us and you said to me something like, Scott, I don't know what I have to share. Well, there's nothing special I'm doing. And I call BS on that every single time. If you've been listening so far, Megan has a little bit of knowledge and ideas to share that are relevant for us. But I think of it as when you're in this position, I think one, my first point is please reach out to me. If you're at the top of your organization, we need to have a conversation. And now's the time of year. You're finishing up the year. So if you're going to finish the year as number one, you've had consistent success. Don't second guess yourself and say, oh, who am I? I don't need to be on Scott's show. Forget that. Call me. Send me a message on LinkedIn, whatever. We need to share your story. And I, part of what I think about this is it's mentoring at scale. Now you can have this conversation with me one time and impact thousands of people instead of one-to-one, one-to-one. It has so much more impact. And I always look at it as if this can impact one person, it was totally worth it, right? If we can change the trajectory of somebody's career because of some little nugget they got, Scott, this is awesome.
35:41 Megan Labadie: Yeah, you made a great point when I was like, oh, you know, me and Sam are so different. She really leans into the books and the podcasts and the LinkedIn influencers. And I was like, gosh, my experience just kind of comes from time in the saddle and having so many good, bad, ugly conversations. So I was like, what value am I going to give to someone? And I was sharing this with my husband, and he was like, you're gonna offer your perspective. That's probably the same perspective that a lot of people have, but maybe they're not as vocal about it. So, we're all different.
36:09 Scott Ingram: Please excuse my soapboxing here, but it's something I certainly get passionate about. And again, I think as you listen to this, you find the people that are stylistically similar to you. So, Megan and Sam, very different approaches. And maybe Sam's approach is one that connects with you better. Awesome. Lean into her, reach out, have a conversation. Maybe it's Megan's approach and maybe like, you know what? You can tell me about it as much as you want, but sometimes I just need to go run into the wall and get bruised and bloody and go, oh yeah, don't do that. There's a door. If you just go 10 feet to the left.
36:39 Megan Labadie: Yes, 100%. And that's why I love everyone has such a different path in sales. And then you get together and you get to learn from each other. And that's why the in-person… I'm so glad we're finally getting back to in-person meetings and it's just so much more impactful.
36:54 Scott Ingram: Yeah, this is the game. So we talked about what you're proud of. What do you struggle with the most? What's the biggest challenge in just kind of your day-to-day in sales?
37:03 Megan Labadie: Now, yeah, I would say it is like a very stereotypical thing that a lot of sellers struggle with is the attention to details. I am super grateful that I work with an incredibly talented solution engineer who always takes amazing notes on my behalf. Like I have chicken scratch in a book. I definitely struggle with that. The organization, we've had a lot of changes at our company just recently, which is where people are mapping to in the accounts they have. And that's led a lot of things on my plate. Which I love. I love being busy, but then sometimes it's like, oh gosh, the follow-up, where did I leave these things? So, I would say my attention to detail is not as spot-on as it should be. My current manager would probably tell you that I rank dead last in my ability to complete my sales forecast every week. Every week I'm like, oh my gosh, I'm so sorry, I'll get it done right now. It's just not what I think about. I will stay up all night thinking about a deal and where I'm at, But updating my notes in Salesforce is the last thing on my mind.
38:04 Scott Ingram: I've never heard that before.
38:06 Megan Labadie: No, I am sure.
38:08 Scott Ingram: That's not typical at all. You're so weird, Megan.
38:11 Megan Labadie: Yeah, I hate that stuff.
38:14 Scott Ingram: The good news is there's starting to be tools around this. I mean, one of the things I'm personally leaning into, I've been doing the ultimate A/B test for folks who have been on calls with me lately. It's obscene because I've been running 6 different AI note-takers all at the same time just to kind of compare them. I realized my default is I'm 80% engaged in a conversation and then I'm 20% taking seriously half-assed notes that are really not very helpful to me in the future. Now, mine's not chicken scratch, it's in Evernote, but it's still not very helpful. I always start strong, but it just fades because I lean more and more into the conversation. I'm like, you know what? There's robots that can do this for me now that I can just kind of trust them. And now I can be 100% in the conversation.
38:55 Megan Labadie: Oh, it's so true. And especially when you're doing deep discovery conversations, and that's very much the role I play, is asking you what your problems are and then continuing to dig in. And if you're not fully engaged, you're not going to have an impactful conversation because things will just hit dead ends. You're not paying attention. It is the best way. That sounds like my get out of jail free card on the note-taking.
39:20 Scott Ingram: Yeah, but I want to talk very specifically about that though. So how are you I mean, especially in that type of discovery call, how are you managing that? I think the typical trap is you're listening and thinking about what you're going to say next rather than actually listening and just kind of following the thread. So, what is your approach? How are you kind of taking notes around that?
39:41 Megan Labadie: I have seen so many new reps stumble with that. When we first launched this team, we grew it pretty quickly and we had a lot of new hires come in and they were just laser-focused on, these are the questions I have to ask, and they were doing exactly that. That, asking questions and then thinking about the next thing they're gonna ask. I'm like, that's not what you need to do. Have 3 questions that are your go-to. If you're completely spacing, write them down. But your job is to ask a question and however they respond, that's where you need to keep going from. You know what you're talking about. So don't get lost in, these are the things I have to do. The only thing you have to do is uncover what their pain is. And the only way you're gonna do that is by listening to what they're saying. And continuing to dig in into that. I see it a lot. I'm sure I'm very guilty of that back in the day, but that's definitely something I try to actively work on is asking those second, third-level questions, and especially paying attention when you know you've struck a chord with someone, and then just keep going on that. And then just asking too, okay, that's how it's impacting you, but how is it impacting internal audit? Or how is it impacting the other teams that you're working on and collaborating with? This, where are you collaborating with those folks? And if you're not, is there plans to do that? It's so important. And again, a lot of people want to be experts and know everything right across, right from the top of getting started, but it's just important to listen to people. At the end of the day, we're all individuals trying to get to the same goal of Friday afternoon, but digging into their pain is where the dollars are.
41:11 Scott Ingram: Yeah. Yeah. It's the curiosity, right? It's being genuinely curious about that. And I think about, cause I'm doing it right now. What people may or may not realize is I have the same list of questions that I have used for the last 180-whatever episodes this is for 8 years on this podcast. But all it is is a flow. It's a reference point to go back to. But Megan's going to say something interesting about discovery, like, oh, that's interesting. It's really having that freedom to… and you mentioned kind of the expertise. The ultimate way to demonstrate expertise isn't what you say, it's what you ask.
41:48 Megan Labadie: Yeah, that's a great point. What a little one-liner that was.
41:52 Scott Ingram: That was pretty good.
41:53 Megan Labadie: That was good.
41:53 Scott Ingram: We'll pull that out.
41:54 Megan Labadie: We'll put some quotes in that.
41:56 Scott Ingram: I'm going to totally have some fun with this. Let's follow that a little bit. Speaking of those questions that demonstrate expertise, how do you think about that? What are some of those questions that you are asking in these discoveries conversations that you're having with your clients?
42:11 Megan Labadie: Without getting into a specific question, I think the best path to take is always asking the most general questions first, because people always have a direction that they want to go down. If you're asking about something pretty specific, like, hey, talk to me about how you collect data, and that's not even something that falls on their radar, well, like, what was the point of bringing it up? So, by asking a question, just tell me about your process, tell me what your role is, or where you're having pain, or where you're struggling, People could say something completely off the wall and throw you off, but most of the time they're gonna land in the place that's most important to them. And that's when then you can ask your subsequent questions that get deeper and deeper into that. Because we can assume what someone's challenges are all day long, but at the end of the day, people's perspective is their reality. Whatever they're struggling with is what they want you to fix. They don't care that you've got XYZ features that can do these things. That's not really important to them. Again, cast a wide net and then get more specific there. And just truly, as Scott and I were saying, just listen intently and pick up on those things that you think other people might just coast over.
43:19 Scott Ingram: Yeah, really digging at what do they care about. One of my favorite opening questions, especially if you're coming into an early discovery call, it's why did you take this call? Why are you taking the time? And then you get straight at kind of the high level. Oh, well, we're dealing with X, we're dealing with Y, and I'm trying to solve. Solve this. Now you know what to talk about. Don't follow… and again, maybe you had a completely different sort of pre-planned… again, for me, it's you want to prepare, you want to have some questions in mind, but to your point, you might throw me a complete curveball. I'm like, that wasn't my hypothesis at all. I didn't think that's what I was going to be asking you about. Okay, well, that's the path we're on.
43:56 Megan Labadie: Cool.
43:56 Scott Ingram: Tell me about it. What's happening?
43:58 Megan Labadie: Yeah, it's funny. On the preparedness side, I had a conversation recently with a company I've been working with for like 2 years, And I did my due diligence. I looked in their proxy statement to see where they were mentioning ESG, and I saw that they were tying their executive compensation to ESG goals, which is like, you're telling me you have no budget? So I was like, oh, okay, you guys are having a hard time getting budget, but your executive comp is tied to ESG. And they were like, wow, I'm super impressed that you took the time to look at that. They're like, actually, we've dialed that back since proxy. But so it was like, okay, here's an assumption I made which got me brownie points, but still at the end of the day was no longer relevant. It's interesting. And I think that's another thing I love is preparing yourself in ways that are not super obvious that anyone can get to. Like, one thing I always do is I look at the proxy statement. I see again, where are those mentions? I look at their peers. I come prepared. I know which of their peers are also using us, not people I assume are their peers, Who are their actual peers they're benchmarking against? Being able to name-drop one or two of those companies, it's game over. It's trust. It's the things that you can't really sell. One of the most impactful things to get across to people is, I am a safe choice because other people are using us, or your company's already using us. It's really hard when somebody risks their career on purchasing an expensive software and it doesn't pan out. Out. So having a solution that is like, this is the one I feel most confident about, even if they can't check every single box, my peers are using them, I feel comfortable, right? There's a lot that goes with that sentiment.
45:39 Scott Ingram: So good. So good. And again, I think this is such a powerful combination, the idea of being researched, doing the preparation, and then tying back to this idea of the questions, right? The way that I see this work really well is going in with an informed hypothesis. I can demonstrate that I've done my work. Here's what I think might be happening, but now let me just put it out there. Like, is that right? Let me validate that and dig into that. And so it, again, it shows that expertise, but then are you asking the right questions behind it? Or maybe you're wrong. Like, okay, but I still saw that you did the work. Like you really tried. Now let me set you on the correct course. Of course, we're going to take a detour here. Megan, let's talk about… I love to dissect people's days, and here's how I like to do it. Your alarm clock goes off. Tell me what time that typically happens, and then I want a pretty detailed run-through of your day till your head hits the pillow again.
46:33 Megan Labadie: Yeah, well, if my alarm clock were to go off, it would probably go off around 7:15. I'm not a morning person, but I also have a 4-year-old. It's pretty rare that my alarm is waking me up. It's usually him. That's barging into my room for one reason or another. So I almost immediately start my day making lunches and then making coffee, which is most important. My husband travels for work also, but when he's home, he does that school drop-off, which I'm really grateful for because I almost feel like my hours between 8 AM and 9 AM are like the only me time I get in a day, time when I can check Instagram, do some frivolous things, throw laundry in. I try to leave that time open because my brain is just not that sharp in the morning. Then it's getting into meetings every day, as you know, looks different. One thing I think that's hard to explain to people that aren't in sales, like my husband, right? He'll be like, oh, do you have a meeting at this time? And it's like, just because I'm not in a meeting on a call doesn't mean I'm not working on proposals or doing follow-up or strategizing on something. Our brains are going 24/7. It's never a typical day. It's never the same. It never ends either. There's always something. There's always another deal to think about. There's always somebody pinging you, asking you for the latest. The day varies, but fill that in with meetings, a 3 o'clock lunch occasionally. I feel like I've done a lot less travel since COVID than I did before. I do miss getting on site with people, but also get so much more done being home all day long. I miss the 10 minutes of conversation before and after meetings. So, you've got to find just other ways to creatively do that and relate to folks. But yeah, that's the day. They invest a lot into our growth here. So, we do a lot of trainings. One thing I also try to do is we've got like true subject matter experts that are in the field, that are doing podcasts, that are doing conferences, that are are talking to folks all day long that are really just in the thick of it. So, I always try to make time in the week at some point to connect with one of those folks and be like, what new things are you hearing? ESG is just a rapid space, so there's always something that I've not heard of yet that is something to learn. And you'd rather be caught off guard by someone you know than someone you don't know, and they'll throw some random acronym at you and you're like, oh, yep, sure, I've heard of that. And you're just like, what is that? Again, trying to also sprinkle in a fair amount of that education because it doesn't stop. My son comes home. I like to love on him. You know, 4 is a great age. I know you've got kids that are older now, but it's that age when you're still just like rockstar status to your kids. So they love you and they wanna know what you have to say and how your day was. So I get a couple minutes of that and then wrap up my day, whatever else I'm trying to work on. I do try to like not have meetings again before 9 or after 4. Sometimes that can't happen, but again, that's kind of my time to wind down the day and make sure I'm not walking away from my computer with 10 things I haven't done at. I'll try to sandwich the workday with those things. And then I'm not like a good cook or anything, but there's a local place here that we get our precooked meals from. And so like I'll put it in the oven and at least makes me feel like a good mom and housewife by delivering a hot meal that somebody else prepared and I just heat it up. So, and like a big reality TV person. So when it comes to at the end of the night, how I want to unwind, like a real Housewives or a Love Is Blind, something like that is where I like to kind of get my mind off of everything because it can be a lot when you're in a seller's brain.
50:13 Scott Ingram: Yeah, absolutely. Such a good flow. One of the things you called out I'm really curious about because I've been thinking about this a lot is, again, in the olden days when we actually went on site and visited with our customers, you called out the most important thing. It was the walk to and from the conference room. It was just these little sidebar hallway conversation things that sort of happened. And how are you trying to get to just those more human truth nuggets outside of the, we're in a Zoom meeting and we act like this and we say this and we just don't get as many of those, again, more human interactions that are so important in our sales cycles?
50:51 Megan Labadie: Yeah. And it's tricky, right? And I think the number one question I hate is like, what's the weather like where you are? Right? Like that's, ooh. But I guess my first question is like, oh, where are you based? Taste, because then I could almost always pull something from that. And then they'll want to know where I'm from, and it's like going down those paths or seeing what things are behind them. Mine's not a… what's on the wall behind them? Is it a model car? Is it a picture of their family? There's a lot of things you can pick up. And then just again, kind of doing your research up front by knowing… not the stalkery stuff like, oh, I saw you went to the University of Maryland… but like knowing what prior roles they've had where they may have done something similar and being able to reference like, oh hey, I saw that You had worked at Deloitte prior. They're a big partner of ours, and whatever that comes from, you got to get a little creative. You got to start immediately getting into questions before everyone shows up. I'd like to show up a minute or two early sometimes. Sometimes people just dial in and they're sitting waiting for the meeting to start, and that's a great time to have, albeit sometimes awkward, conversation. But it's often our only chance to do that. And then getting people on site at some point, driving them to a conference or like, hey, are you going to XYZ industry event? Trying to make those personal connections. Let's meet up for lunch. I'll text you. And now I'm on a texting basis with someone. So really thinking through a bit more strategically of like, how can I build a relationship with someone when I'm just on the other end of a computer?
52:17 Scott Ingram: Yeah. Yeah. It's so funny you call out the texting relationship again. I mean, that's another place where not having all that onsite stuff messed up my game because one of the easiest ways to get into that text conversation is, oh, hey, I'm coming onsite. Site, give me your mobile so that when I get there we can kind of find each other and that type of stuff. That was one of the easiest ways, like, okay, cool, now we've opened up that channel. Any tricks that you're using now to sort of open up? Because that is such a valuable channel where there's way less noise than the email and the phone they don't pick up and the LinkedIn that's noisy and just all the stuff.
52:53 Megan Labadie: Yeah, I mean, I definitely had to get comfortable with being All right, if their mobile's in their signature, then I'm going to use it. And I think too, like, how do I prefer to be communicated to? Text message is pretty easy. It's a pretty easy way to like let someone down or like whatever the message may be. So sometimes you take a swing and someone's going to ignore you, but you kind of got to go for it. I'm sure anybody who's listening on the customer side's like, oh my God, please stop spamming me with your texts. But if it's personal or fun, like I was just on with a customer and we were talking about, she handled the reporting side and we were on with their carbon environmental team. And I sent her like a meme while we were on the phone because I already had her text of like a little girl being like, what, what are they talking about? And she like responded with a cry laughing emoji, right? So it's like, it doesn't even need to be anything important, but just like I could tell her and I were both like, this conversation is beyond our realm of understanding. I want to see her smile as she picks up her phone and laughs at it, right? So yeah, it's a delicate balance.
53:56 Scott Ingram: Yeah. You know what, one of my moves I'm realizing, I'm like, oh wait, there is a thing that I do, and it really matches just kind of my own preference. Even when people I know call me, a lot of the time I won't answer. I'm like, I'm in the middle of stuff, this is not a good window for me. And what I appreciate is, hey, send me a quick text and, hey Scott, can we connect at 4:30, or are you open this afternoon? So that's what I'll do. I'll open with, hey Megan, it's Scott Ingram, right? That first one you sort of want to like, okay, cool. Let's associate my name with my phone number. And it's like, I need 10 minutes. How is your schedule this afternoon? So now I've opened up that channel and we found a time that they're actually agreeing to a call rather than me. I'm just going to try you out of the blue and there's probably 80% chance you're not going to pick up the phone.
54:36 Megan Labadie: Yeah. Because I don't pick up the phone when a random number calls me either, but like a text message, it's like, oh, now I already know who it is. I don't have to type it into Google while my phone's Phone's ringing. ringing.
54:45 Scott Ingram: Yeah, yeah. As you're working through your day, how are you managing kind of your to-dos and your priorities and just all those things that need to get done?
54:53 Megan Labadie: Again, probably one of my weaknesses. I'm like an old school, let's make a list. I have to get these things off my brain, especially at night. Like, if I wake up in the middle of the night, there's nothing worse than being awake from like 2 to 4 AM and you just can't go back to sleep because things are on your mind. I hate picking up my phone while should be sleeping, but it's like, if I don't put it down in my notes, I use my Notes app a lot, I can't let it go. It will fester in my brain all night. So I have to just jot it down. I also try to like get accountability through Slack channels and things like that just to stay organized. If anybody's got some good tips or tricks for someone like me, please feel free to hit me up on LinkedIn because I'm just old school on that. And I know that there's probably things that inevitably slip through the cracks, and I'm going back and searching for emails, and it gets tough. So, yeah, I don't have a great answer.
55:45 Scott Ingram: What are the tools you're using? So, here's what I've captured so far. You're using the Notes app. We've got chicken scratch in a notebook. I heard Slack. We're not participating with our CRM the way we should. What else is in the mix?
55:57 Megan Labadie: Yeah, that's pretty much it. I mean, seriously, again, we use Zoom technology, so we've got like our… it will capture notes and recordings, and watching back those recordings is something I like to do if people are comfortable with that. It's hard to take it all in. So I'm grateful we've got SalesLoft as a tool we use. So it's really nice to be able to have features where you can see if people are engaging with your emails. We also leverage a tool called Consensus. So you can actually send like little short demo snippets, which I love. You can see if it's being forwarded and who's watching it. And it just is a better way to interact with people knowing they have or have not taken that next step. It's also something, if we go back to the point of being able to really dissect where you're at in a deal, if people are taking a lot of time from you and they want to see something again and again, it's like, I'm going to use this technology to send you an abbreviated version. And if you're not engaging with that, I know where I stand and I'm going to continue to invest time there. So, we've got a lot of different tools, as most companies do leverage. I like some of them. I don't use all of them, I'm sure. But it's just about finding what works for you and what can help you in the day-to-day. And not immediately. And I think a lot of people are guilty of this when like something new gets rolled out being like, oh my God, another tool. But they're all designed to solve problems for us. I think we're implementing one for like a reference software now and like how can we better manage our references and incentivizing them. So those are things that we really struggled with in the past. And now we have a tool that can help at least organize that. So it's all headed in the right direction. And using AI often is now something I like to do too, although I don't know how much we're supposed to be using it. Still blurry to me.
57:37 Scott Ingram: Yeah. What about your information diet? What are you reading? What are you listening to? What are you watching? And when does that happen beyond the reality shows at the end of the day?
57:45 Megan Labadie: I knew you were gonna ask me this question and my answer is so embarrassing to me. I don't even wanna share that. That's just, that's not where I go, books and things. I do listen to podcasts. Most of them are entertainment-based and I do listen to yours because I've now come to know you and love that, but I get most of my information through LinkedIn. I'm a big LinkedIn surfer. If I spend too much time surfing Instagram, I'm just spending money and doing things I shouldn't be, like getting fed up all those blue sky technology that we used to leverage back in the day to all those relevant ads I get. So I like to get on LinkedIn, spend my time scrolling there. I'm really good at trying to leave comments if it's something my customers or someone I'm trying to sell to is doing, just to know that not only did I see it, but I didn't just give it a thumbs up. I said I'm like, oh, that's amazing, or super cool. And I know that that elevates their post as well. So I spend a lot of time there. I like to share those articles. I'm like a quick read, give me the blog post version of something. And then again, we do a lot of training here. We've got weekly meetings that are far more organized at this organization than probably any other place I've worked, and just a lot of knowledge sharing. And we're starting to get back into role-playing, which I think a lot of tenured salespeople tend to roll their eyes at. But it is important to go back to the basics sometimes and get those tips and tricks from others.
59:08 Scott Ingram: Love it. You may have hinted at this earlier, but I'm curious if you subscribe to a particular sales philosophy.
59:15 Megan Labadie: I feel like I've been through a lot of sales philosophies and I probably take a little bit from each of them. Like I've never once gone through, I've done Challenger Sale, I've done Franklin Covey, we're going to read every book, Never Split the Difference. There's a lot of different philosophies, and I've never read one and been like, whoa, that's so transcendent. But I have taken bits and pieces from each one, and I think that's really how you get more well-rounded, is like the more you open yourself up to… you can't just listen to the same thing over and over again, which is really why this podcast is so interesting, because you're talking to people from so many different backgrounds and different sets of experiences, and that's what makes everyone unique and how you can learn a little bit from each person. So, yeah, like I said, I mean, I take a little bit from each. I love the, from the challenger, really that teaching, becoming. I never sit across from someone and say, like, I am a subject matter expert in ESG, because I'm not. That's their role, and I'm here to educate them on what we can do. But really taking on that, how can I educate you on what it is that we do and make it seem like I'm just genuinely trying to help you, and that is true, versus like, I'm just trying to get my product in front of you. So, uh, take a little bit from that. Franklin Covey gave some great sending those emails before you have a demo just to be like, this is the agenda. This is my expectations. Like, is there anything you forgot? Anything that you want to talk about that I haven't covered yet? Little things from every sales training. I think you'll find what jives with you and what fills those gaps that you might have. So I think it's important to just be well-rounded in that area.
1:00:51 Scott Ingram: Yeah. Love that. I mean, I really do think that's the ultimate answer, right? It's being, I think of it as being a student of sales. You explore kind of the different philosophies, but it's not, oh, I'm going to do everything that that system dictates and I'm going to say it all the same way and that's not going to work. It's really, you kind of cherry-pick. You're like, yeah, let me try that. You're like, oh yeah, that actually fits really well. I'm going to always wear that pair of shoes. And over time you sort of develop your approach.
1:01:15 Megan Labadie: Yeah, 100%.
1:01:17 Scott Ingram: Megan, within that approach that you have developed, what's your style?
1:01:21 Megan Labadie: I say it all the time and I've probably already said it on this podcast here. Like, again, I try to be the everyman. That's what I say. Like, I am not that expert. I try to really relate to, this is complex subject matter we're talking about. And again, I never want to put on my hat. And some people do it really well and can sit across from an expert and speak to them at their level. But again, I just really try to take those problems, expand them, and make it so that everyone in the room, regardless of their role, can say, that's how that's going to impact me. So how can we make the problems wider? And how can we make the understanding of what's at stake here simpler to understand? Like, there's a big regulation right now in Europe around ESG, which is the corporate social… anyways, CSRD. So like, this is a big… and I'm on the spot, so of course I'm not going to think of what it stands for, but there's a big regulation there that's impacting everyone. And these folks in ESG, they understand what it's going to take, but again, Like the other roles in the organization, it takes them longer to get to why is this such a big problem? Or why can't we just solve it with consultants? Or hey, we've been doing it just fine until now. What's wrong with status quo? And the fact of it is you can't assure data that's been collected through email and Excel and Microsoft Word. It's just not an effective way to work. It's not consistent. There's no integrity around your data. You've got no audit trail, and this stuff needs to be audited. It's really understanding which part of the regulation is going to impact everyone.
1:03:01 Scott Ingram: I want to talk a lot more about this really from an enterprise sales perspective. So you're in an environment where your average sales cycle is a year and a half. We've already talked about just at a high level, all the stakeholders that are involved in your deals. What's your approach to just managing all of that complexity and all of the different kind of personalities and all of those pieces that you just kind of alluded too?
1:03:25 Megan Labadie: Yeah, my biggest piece of advice is we have a lot of champions of our product. Our product is used for many regulatory compliance reports, but mainly around financial reporting was where we got our start. And we have really dominated that market, and we have a lot of very loyal, very happy customers, which I know is like a very privileged place to be. It's incredible. But often And those are finance folks. And now I'm working with someone in ESG, and those folks roll up to legal, sometimes marketing, sometimes finance, right? Like, it's different across the board. So, I always know that my biggest ally is sitting at that company. Somebody who has already taken a risk to purchase our software, is happy with that software. You got to validate that, make sure that that's the truth, and then make sure that they're involved in the process as well. So, usually I won't invite those folks to like a discovery call because they may not have a lot to add into, these are the pains of my process. But when we are demoing the product, you're going to believe that I am going to reach out to our champions. And this is so important and not enough people do this, just to be like, hey, I'm meeting with Scott on your ESG team next week and would love to have you sit in to provide your context of like how you're leveraging the tool today. There are certain things in our demo that I know are Like crowd pleasers, so I will take a pause and then be like, "Hey Scott, so just interested like how you guys are leveraging that today in your own organization." And then also using that on the flip side too. Like a lot of times when people are saying, "Hey, I would love to talk to a reference," sometimes people ask for a reference like the second you get introduced to them, and it's something to navigate around. I always say like, "Hey, your best reference, by the way, is sitting in your own organization. Someone who knows how you guys operate." what your policies are and how our software relates to that. That's the first person you've got to go talk to. And then often those people, like, if they really like the tool, they'll do their own demos. So when I get on to demo to someone and they're like, oh, actually I already had a chance to sit down with Scott and he showed me his instance, I'm like, oh, beautiful. Now I'm not even doing the selling. Yeah, they've done the selling and I'm just here to facilitate the conversation.
1:05:37 Scott Ingram: That's really good. What percentage of your time, so as you think about a big deal, how much of your time is spent working with that client and in conversations with them versus with your own team and just kind of internal work that you're doing on their behalf? Like, how would you break that out?
1:05:56 Megan Labadie: I mean, they're all different, but I would say if it really boiled down to it, it's probably 50/50, if not so a little bit more on the internal side, which I know can be painful at times to have so many internal meetings to discuss things. But again, we have the ability to bring in so many different personalities or people with different strengths in our organization, right? We've got a value management team, we've got subject matter experts, we've got solutions engineers, we sell other products that complement these things. We've got someone that can speak very eloquently about delivery. We've got partners to bring in. All of those conversations take take planning and how are we going to do this and what role is everyone going to play and what is our goal at the end of this conversation. So I think that there's definitely a lot of time spent internally to navigate those things. And then the time that you're on with the client, you're going to have plenty of meetings that I think, again, early in my career, I'd get super excited. I'm like, oh my God, a CFO just accepted my invite and they're going to join the meeting. But like, those are not the most impactful conversations. Most impactful conversations is 1 hour, 1 day after we had that demo, and I get back on the phone with my champion to be like, how did it go? What was the feedback after we were in there, right? So those are my favorite conversation to have. They're also a great place to sort of build that rapport that we were talking about. You know, at the end of the day, if you know what their goals are and their pains are, and you know that you can solve those, and you feel very confident in your ability to deliver on It just does wonders for your confidence in a sales cycle.
1:07:30 Scott Ingram: Yeah, I think what you just shared is so common when I ask this question of enterprise sellers. The more complex the deal, the more time you're spending internally, which is so counterintuitive because you think this is a huge complex deal. I have even more stakeholders than I do on simpler deals, and yet it's fifty-fifty at least, probably more than that. That. And yet we don't ever talk about how are you managing the internal side? So let's talk about that. What are your strategies? What are the things that you're doing to… I mean, I think of it as wielding your organization on behalf of these clients, and you might have more internal stakeholders than you do on their side. So how are you just managing all of that?
1:08:15 Megan Labadie: Yeah, it's interesting. And I think I've had different sort of philosophies based on what I'm selling. So, in the past, right, I would love to get executive sponsorship and facilitate those conversations. But now, I really like the more subject matter experts from our organization coming in to talk about something that they know a lot about. Because a lot of the subject matter is still relatively new and it's evolving, those conversations give us so much credibility versus like a kiki between an executive and another executive that may not really even know know what problem we're solving. That gives you some brownie points on the back end, but really getting into… and again, I'll go back to the regulations in Europe. We've got a whole team of people that are experts that live in Europe. And sometimes I'm like, I understand that for an American girl to sit across from somebody sitting in Europe and telling them what they need to do for European disclosure is probably like lost on them for sure. How can I bring in someone that's going to add a lot more credibility than I have to Really leaning into the resources you have at an organization, getting creative about how you use those resources as well, I think is really a big differentiator.
1:09:29 Scott Ingram: How do you just manage all of those internal relationships? Because I'm sure this is, in your world, dozens, maybe hundreds of people that you might bring into a deal at any given point.
1:09:38 Megan Labadie: Yeah, it's definitely tough because there are, to your point, a lot of people depending on what you're trying to accomplish. I think when you're a seller and you tend to be the one that gets your name in lights and things like that, it's important to go full circle back to those folks that have helped you and be like, hey, this is how the conversation is continuing to progress. Really make sure you're showing them the appreciation and love that they deserve because they are really serving us very well. Stay engaged with those folks and then they'll remember that. It's not just a one-off conversation that you popped in and had and threw on their calendar, but you prepped them for it. You gave them all the background they need so they feel confident and continue to elevate them and keep them in the loop and give them their flowers as well when things go in the right direction.
1:10:24 Scott Ingram: Yeah, I'm going to tie 2 ideas together because I think in a lot of ways it's the same way that you would manage sort of a mentor type of relationship. A lot of times the most valuable thing for them is, I just want to know I was helpful and that I impacted you and circling back and saying, hey, Megan, you had suggested that I do this and I tried this on this last deal and it worked freaking great. Thank you so much. Which keeps that door open right now. I can go back because, oh, this person actually listens to me and I'm happy to help them. Like, it fulfills me. I think the same thing is true of a lot of these internal folks. Like, they just want to feel like, hey, awesome. Like, I'm not in sales. I don't get a commission for this, but I want to know that I impacted that deal, that I made a difference, that I kind of know how this is progressing is so, so key. Anything else that you're doing just along those lines to, because again, I think it's really recognizing none of these people report to you. They don't owe you anything. And you're competing with the rest of the sales team with some of these resources. Keeping all of those doors open so that you can pull on those people when you need them, I think is really, really important and way overlooked.
1:11:27 Megan Labadie: I think too, right? A lot of times it's all in like the introduction of like how you introduce those folks to your customers. Being like, Scott is an absolute guru when it comes to this. He's got such a great perspective. He educates on this really well. Again, giving them all those kudos in front of other people too is like, I want to pump them up first and foremost to my customer, but secondly, for themselves. There's nothing better than talking to someone when someone's just made you out to be this amazing person. You feel great. So, it's so important to really lean in on those conversations when they have have open hours, show up to those things. If people aren't going, that's your opportunity to really learn and dig in and keep in on other channels, different Slack channels. I don't know if there's another version of Slack. I'm sure there's a competing technology that I think Microsoft has, but on those threads, make sure that people know that they're important to you.
1:12:21 Scott Ingram: Yeah, absolutely. Megan, is there something you believe that the average or typical sales professional would think is Oh gosh, such a tough question.
1:12:34 Megan Labadie: I don't know, maybe not that they would think is crazy, but I think going back to like my uncomfortable conversations, really sticking up for your organization when things have gone sour, sort of that idea of the customer's always right is only relevant sometimes. I had a situation recently where we had a couple years ago, so not that recent, But we had sold our product and then they were like, hey, it's not working as you said it would. I'm not happy. We want to terminate the contract. And I really took a step back because that was not the experience of any other customer. And I got with my customer success manager and I said, all right, what can we dig into here? And he's like, well, they never took the suggested trainings. They spent 1.5 hours in the system since we implemented. So like, I took all that and was I was like, okay, this is an uncomfortable conversation because this is someone's job on the other end of this. But also at the end of the day, it's our reputation that's on the line as well. And I can't have you drag me through the mud and my product through the mud and our, all of that when you just haven't put in the time and effort. It was kind of a contentious conversation. I was nervous to talk to the procurement person, was the one who brought it up, not like the the user. And I was like, listen, I'm going to lay it all out. I'm not trying to get anyone in trouble, but like, this is the situation and how it played out. And he's like, you know, it's really funny you said that because I kind of got the same vibes. Like, the story kept changing. And I was like, oh my God, here I was so nervous to bring it up. And he was kind of like, I kind of sensed that that might be the problem as well. Learning when you can absolutely own what you've done wrong, but also recognize that you don't have to own up to things that you haven't failed at. Some people might think that's crazy, but you can't let people walk all over you. And oftentimes that happens to salespeople.
1:14:25 Scott Ingram: That's so interesting. And I have certainly seen that where somebody is basically not doing their job and it's way easier to scapegoat a product like, oh, that didn't work. It's like, no, actually you don't work. I mean, again, very sensitive, very tenuous, very… yeah, there are some tough conversations in there, but sorry, I'm not taking the fall on this one.
1:14:46 Megan Labadie: Yeah, things are back on track with that client. Like, they assigned someone new to work on it, and I said, hey, we'll give you some goodwill hours, but I'm not doing it unless you agree to go through these trainings as we suggested. I'm willing to give to you, but you need to prove to me that you're willing to put in the time, because this is time and effort now on my side that's taking hours out of my day I'm not getting paid on, right? You have to get comfortable with be uncomfortable.
1:15:11 Scott Ingram: Yeah, that's awesome. That's awesome. What about the flip side? Is there something that the typical salesperson believes or that is just part of sales dogma? Like, oh, everybody thinks this, that you think is, no, that's not right. That's wrong.
1:15:24 Megan Labadie: Ooh, I think people that aren't in sales think that sales is really easy. People sometimes think sales is all just like shaking hands and steak dinners. And I used to joke that for every steak dinner I had, I would also have like one venue machine meal from a Courtyard Marriott when I'm getting in at 11:30 at night in Cleveland, Ohio. So sales is not easy. I'm lucky to be having some of my best years right now, but I mean, a career's worth of… you think that the sky's the limit and the grass is not that green and you're working for tough people or you're working for… I've had bosses that were so different from me that that really just don't know how to manage people well or don't know how to manage to different types of personalities. I would say nobody at my current company would say that I am timid or shy. I'm always someone that speaks up for things. And I have had a boss before being like, I don't know, you're just kind of timid to talk about this. And I was like, what? He was so aggressive and, oh, she didn't get back to you, go to her boss, a way that didn't jive with how I like to operate and just couldn't read the room and didn't care and just wanted to bulldoze his way through things. And that just was totally different from how I like to treat people with the golden rule, treat people how you want to be treated. We didn't get along. And I think that's what really led me to one of my 3 reasons that I've gotten to the top is working for people that you have respect for and that you like, and that also bring something to the table.
1:16:51 Scott Ingram: So good. Jack Wilson just shared a point about this in the Sales Success Society. And hopefully by the time we release this episode, I'm going to get him to do a tip on the topic. But he was talking about alignment and he was talking about a period where he's like, yeah, there was like this 3-year period where I couldn't find it. I felt like I was doing all the things, but it just wasn't there. And then more recently, he's just found all this alignment between the types of clients he's working with, the work that he's doing, who he's working with, to your point. And he's like, I haven't changed anything, but everything is working right now because I now have this alignment. And I guess my question to you is, I guess there's 2 parts. Like, does that resonate? But also maybe tying it back to just longevity in this space, because it sounds like you've gotten to this place of really strong, consistent success, but it's not like it's always been like that. How do you get through all of the hard times and know there's still a rainbow on the other side of this? That freaking pot of gold is there. Before we give up?
1:17:56 Megan Labadie: Oh gosh. The second part, I mean, it's kind of like buying a lotto ticket.
1:18:00 Scott Ingram: Yeah.
1:18:00 Megan Labadie: The most fun part of buying a lotto ticket is imagining what you're going to do if you win the lotto. And then you don't win the lotto and that happens, or hopefully you do, right? But it's just knowing what's possible out there. And at the end of the day, I'm a people person. And I think kind of to your point of alignment is I know enough about the subject matter expert to be dangerous But to have comfortable conversations with people. I'm not constantly reaching and explaining things I don't know about. I'm just trying to, again, dumb it down, make it simple, make it basic, be someone who's relatable and easy to talk to. And then the good stuff follows. But yeah, I mean, territory, time, all that stuff plays into it. You've gotta have the right tools. There's been products I've really believed in and then just the timing wasn't right. Again, what I'm selling now, we tried to sell 10 years ago. And there wasn't really a big need for it. Everything's changed now, and it's about finding really what you're passionate about. I think there's so many things that go into it. It's easy to get burned out as a seller, for sure. I think we all go through it many times. Like, when you're hot, you're hot, and when you're not, life is not that great. So just trying to find a balance at the end of the day. And I often say, guys, we're not doing brain surgery here. This is not life or death. We're selling software. Where we have to remember that we're here to help people, but this is not what I'm going to like get too stressed out about. And I think learning to manage that and getting better at recognizing your deals, that kind of all comes, plays into that alignment part too.
1:19:36 Scott Ingram: Yeah. What advice do you have for somebody that is just starting out in their sales career today?
1:19:42 Megan Labadie: I think the whole mentor thing, whether it's formal or informal, really reach out to other people. You'd be surprised. I had gone back a couple years after I graduated college and spoke to one of the groups that I was in, and I was just like, hey, I encourage you all to like reach out and connect to me on LinkedIn. And there was like 30 people there, and I was like, I guarantee not 5 of you will do that. And I think 3 people did. You have to be bold. You have to ask for what you want. I did 4 internships when I was in college, and people are like, how are you getting all these internships? I'm like, I applied. I'm not doing anything special. I would meet somebody out and be like, oh, where do you work? Oh cool, are you guys looking for interns? Like, just be bold, be bold. You're gonna fail. You'll have things that don't work out, but you'll be surprised by how many doors open up by just asking what you want. Don't be afraid to have tough conversations, whether that's with a client, with your boss, with a prospective boss. If you're trying to negotiate on offers, I always think that's really interesting. It's like, I like to negotiate a lot on my deals because ultimately it should still be part of the sales process. If you're evaluating me as a seller, you should want someone who's who's tenacious and wants it all and is gonna fight for it. My last role I interviewed for, the one I have now, we got to the end of the interview and they were like, do you have any questions for us? And I said, yeah, when can I expect my offer letter? That's a pretty bold thing to say, but that's kind of how you want people to close on things. So it's like, don't be afraid to have those types of off-the-wall conversations.
1:21:12 Scott Ingram: So many great points. I mean, this is something that I've been really trying to show my daughters in action of You can have these relationships and it's really just a matter of asking for what you want. And one of the really, I think, counterintuitive things is the more intimidating somebody is, the more you're like, oh my gosh, everybody must be coming to them. Everybody must be asking of them and wanting their time and all of this stuff. I think the more everybody else is afraid. So you being bold and going and asking those people It's actually more likely to break through. Think of this from an influencer perspective. You might think of, oh, this person wrote this amazing book and they're all the buzz right now. I bet if you reached out to that author and just said, hey, I read your book and I have this, that, and the other thing, they'll talk to you. You'll have a conversation, like ask a thoughtful question. They'll get back to you. This is such a consistent thing and it blows my mind how people just blow things completely out of proportion. Frankly, it drives me crazy on the show. I love hearing from people who listen to it.
1:22:19 Megan Labadie: Yeah.
1:22:20 Scott Ingram: And I don't hear from very many.
1:22:21 Megan Labadie: Oh.
1:22:22 Scott Ingram: Isn't that so sad? But again, it's an intimidation factor. Like, oh, Scott has this huge show. There's so many people reaching out to him. It's BS. I have plenty of bandwidth. Send me a note. I'd love to hear from you.
1:22:36 Megan Labadie: Yeah. And on the flip side too, this is kind of a fun story, but when I was working at a really, really small startup, I got an email from the person from the business fraternity I was in that was in charge of alumni relations. And it was just a cold email that I'm sure she had to do quarterly or some sort of cadence. And it was so funny. The subject line was funny. There was all these plays on what was happening currently in the world and in pop culture. And I responded back like, I don't know what she was trying to get at in her email, but I said, I have to meet you. I offered to take her to lunch. I hired her as an intern, and she's now become one of my closest friends. And I just adore her. I was like, I have to meet the brain who came up with these things. Like, you're so creative. And she's like, I'm really glad you reached out. Somebody else reached out and was like, I thought it was really inappropriate, your email. Like, this is not what we're about. And I was like, 2 people had completely different feelings about her email, and I absolutely loved it. I thought, what a creative way to get someone to read this.
1:23:36 Scott Ingram: So that is such a great example of, I think, when you are like super authentic like that, I bet the other person that gave her that feedback is probably not somebody that she would jive with anyway. Not connecting with me, this isn't going to work good. If you don't get my stupid sense of humor and enjoy that just a little bit, this isn't going to fly.
1:23:56 Megan Labadie: Yes. I'm also like the queen of dad jokes, I call them, throughout my demo. I try to sprinkle in things. I'm like, come on, guys, software demos are not super exciting or engaging. So I try to like sprinkle that in and half my jokes land and the other half are flops, but I take my shots.
1:24:10 Scott Ingram: Totally. Totally. What about your advice for somebody that is now first further into their career and they're doing okay, like, cool, I'm at my number or whatever, but they just haven't found that gear to greatness. What do you tell them? How do you find that, okay, now I'm actually doing it?
1:24:25 Megan Labadie: Yeah, this will go back to sort of the education side, and I think it's harder for people that are a little bit stuck in their ways. We record a lot of calls at my company, you know, just to use internally to reflect, to give to new hires. It is so important to listen to how how other people are pitching your same product because you're going to see, first of all, just hearing someone else pitch it for the first part, or even just watching yourself back, seeing the reactions in the faces, seeing what's resonating, hearing something that you're like, gosh, I never thought of that. That's so great. It's probably our greatest thing that nobody really takes advantage of is just sitting in on other people's calls, shadowing calls. 3 years into it, I'm just going to hop onto somebody else's this call. Like, our managers get to do that all the time, but we don't really do that to peers outside of a new hire. I think that's the best way to really get perspective, to change it up. If you've been doing something the same way over and over again and you're having just an okay, right? You got to look at yourself and not say, oh, you know, it's XYZ reasons why I'm just doing okay. Open yourself up to how other people are doing things and ask questions, be curious, Ask for feedback. People don't like to give unsolicited feedback and hurt people's feelings in a work environment, but I'm always asking for feedback. If someone shadows on that, like, hey, what did you like? Where do you think I could improve? What's something that you would say I needed to focus better on? Or how many times did I use my filler word, right? I think it's really important to look to your peers, folks outside of your boss, to give you that feedback, and don't be afraid to ask for it. For it.
1:26:00 Scott Ingram: How are you asking for the feedback? Because you called out, like, people are often uncomfortable with it. It's like, look, I'll let you go first and then I'll share some of the things I do.
1:26:09 Megan Labadie: There's nothing I hate more than when somebody goes, no, no, I have… like, I thought it was perfect. It's like, clearly it was not. There are all things we can learn from. And you kind of got to push people sometimes. And maybe it's like, hey, especially if they're new to the organization, you can kind of give them a little more tasks than someone who's been there for a while. But like, hey, what I'd like to do, like, I'm happy to have you shadow my call, but at the end of the call, I want you to highlight in email 2 things that I've done really well and 2 areas that you think I could improve upon.
1:26:35 Scott Ingram: Maybe being direct and making a little assignment for it, right?
1:26:38 Megan Labadie: Because nobody wants a whole bunch of people just joining in on their call. So it's like, hey, let's make this a win-win situation.
1:26:44 Scott Ingram: Yeah, that's a really interesting idea. Like really the setup. I want you to be listening for, so it's not kind of this blindsided thing. It's positioning too. I can only get better. I can't get better without that outside perspective. And again, just making it safe. I mean, I almost always joke, look, I've been in sales a really long time. It's super hard to hurt my feelings. So true. Come at me. Don't worry about polishing it or hurting my feelings. I can do that sorting in my own head. I've got a really strong filter. I'll be able to take in the actual nugget of what you're trying to share. So don't worry about my feelings. Again, maybe that helps, maybe it doesn't, but I love the upfront kind of, if you could watch for these things and I'd love to kind of give your perspective afterwards. One of the other things that you shared is really fascinating to me is you had talked about how oftentimes your customers will demo your software. How often do you get to watch those? How often do you get to watch your customer show what's important to them?
1:27:39 Megan Labadie: I actually rarely get to see it. They'll go and have those conversations. And when somebody says that their peer has demoed to them, it's super exciting to me because I know that they're not just going to be like, it's not great, but let me show it to you anyway, right? They're sharing it because they really like it. So I think it's a good indicator. So yeah, I would say it's pretty rare I get to see that, but that's a great point. I should really try to facilitate that more.
1:28:05 Scott Ingram: This idea is really intriguing me as well. I don't know that a lot of organizations are in that place where it's like, could I actually get my customer to demo my own product and show off what's most important to them? I think maybe a Softer way would be, and often this is a champion type situation, like oh you're going to be sharing this with your leadership, or I'm getting ready to present to your leadership. Here's kind of what I was thinking, but getting their feedback of what do you think they think is going to be most important? If you were in my shoes, how would you position this? How would you order these points? Do I have the language right? And again, maybe in a perfect world you get them to. Why don't you just role play with me? Like you're me now. Give me the five minute version of what this is, and just being able to pick up on what is their language, what are they emphasizing? Because it's also probably speaking to oh this is what's resonating with them. They're reinforcing those ideas.
1:28:57 Megan Labadie: Yeah, I think this is another really funny interaction I've had is again I've sort of worked with a client who is now one of our sellers. So it's a very interesting dynamic because they're true like subject matter expertise. Like we have very different styles because she can say things that I can't. I haven't been in their shoes, but when she first came on board, I was like, I gotta ask, what did you think of me throughout the sales cycle? Now, this was an RFP, not the most engaging of them all, and they looked at 20 vendors and all that, but you have several demos and you get to these conversations, and when you win an RFP, you've had a lot of interaction with someone. And I said, what did you think of me throughout the sales cycle? And she goes, to be honest, I didn't think of you. And I was like, ooh, what a dagger to the heart. I was like, that is one of the harshest things, but also such a reality check. This is a blip in their day. So again, getting back to having someone in their own organization demo to them, like, we think that we are the star of their show. We're not. We're a very small aspect of what they're working on day to day. They leave our demo and they may They love it, but they go to do ten other things, and then they don't think of it again. Getting that engagement from people that they truly trust is such a big advantage.
1:30:12 Scott Ingram: Yeah, and such huge perspective. I mean, if you think about the biggest deal you're working on right now, and how much of your attention it has, and then think about how much of the attention of your buyer does it have? It's like, oh my god! This is one of twenty things I'm working on. Like yeah, I need to do this, but it is so low. On my list. And again, you just have this disconnect of priority and just being real about that. Like, yeah, maybe that's why I'm not hearing from them. They've got 10 other things they're having to deal with, and that doesn't include all the weirdness that's happening at home.
1:30:46 Megan Labadie: Well, and that's why I love a good breakup email when you haven't heard back from someone. It's like, hey, I guess you've moved forward with other priorities. And then they're like, oh no, no, we're still interested. It's just XYZ. And now it's at least I know when to follow up with you and not just these aimless emails. I think a breakup email has like a 50% chance of getting a response.
1:31:04 Scott Ingram: Yeah, absolutely, absolutely. Megan, what are the things that you would want to know from the top salespeople in other organizations?
1:31:13 Megan Labadie: Yeah, I think finding out what they struggle with on the day-to-day, where they really see opportunities for growth. One thing I also love is something our company has rolled out is sort of this Top Performers Academy. So I got to do it last year, and they take 10 people who were at the top of their game, different products, and we all got together. And I think what was so impactful is that I would never cross paths with these people really if we're different territories, different products, and we're coming together with such different perspectives and different ways to go through it. So I feel like I learned so much from that and just knowing like, what are your struggles? What are your strengths? What's resonating with you or what's resonating with your customers? And just really getting that feedback. We often have these big sales meetings where the whole company is there, but you end up with the same 10 people that you're chatting with every day. So it's like you really have to expand your horizon and go from there.
1:32:09 Scott Ingram: Yeah, gosh, I love that idea, that whole Top Seller Academy. It's really too bad your organization didn't want to be named because I think we would say some very, very flattering things about them.
1:32:18 Megan Labadie: I know, I love the company that I work for, and whatever, I can understand they they probably are like, oh, Megan, she's a liability. Who knows what she's gonna say? I've worked for many companies and there's a reason I've worked for this particular company twice now.
1:32:32 Scott Ingram: Yeah. So good. You said something else that was really interesting to me, which is this idea of really finding opportunities to grow and just having the awareness around that. What is that for you right now? Where's your biggest opportunity to grow?
1:32:46 Megan Labadie: Yeah, I think that I do need to take on more of a leadership role and I think think, again, not like a management role, but I do need to actively reach out, mentor more people, be willing to share that, and then get that in return. Again, for me, that's the most impactful way to learn, is seeing how other people are doing it. Anytime I listen to somebody else give a demo or deliver a discovery call, I pick up something. It may not be something big, but it's like a one-liner or something that I can use, a cheeky little joke to go along with something. I just really think that that's the most impactful time is getting one-on-one time with others, especially when you have new hires in an organization, someone that hasn't already been molded to how your company thinks. Those are the opinions that I want. That's the perspective that I want. I want to hear how they're thinking through things.
1:33:36 Scott Ingram: That concept. So DeJuan Brown, who's been part of this community forever, super OG, was on the podcast very, very early, spoken at multiple summits. He shared, think the ultimate philosophy around this. It's his own, but something that I think we're really trying to incorporate in so many ways, particularly in the Sales Success Society and with the summit. And it's this idea of learn, teach, learn. So you learn something, and the most powerful way to reinforce that is then teach it to somebody else and then learn through their application. Again, it's a never-ending process. Oh, I've learned this. Let me share this idea. This is what I need. When you talk about managers that are great for you, the perfect manager for me is… we'll go back to our diamond analogy. I need a diamond polisher. I don't need you to give me a lump of coal. I already got the lump of coal. But how can we together really work on… actually, I'm mixing my metaphors here, right? Because I'm talking about like the rough diamond. I've already got it. It's rough. But if we work together and bounce ideas and kind of talk this through, we can really polish it and hone it and make it super special. That's where I get the most value. I basically learn through conversation. I mean, just the riffing that we did earlier, like, wait a minute, what if we had our customers do a demo to us so that we could understand what it was? Or what if they were presenting to their leadership? What would they be emphasizing? Those kinds of ideas are usually what I walk away with. I think it's such a powerful approach to accelerating learning, to really leaning into those things that you're trying to get to. And it also puts you in that position of the do as I say, not as I do. I'm like, oh crap, I can't be telling you to do these things that really it's a message to myself and I kind of need to be doing that.
1:35:18 Megan Labadie: Yeah, 100%. I love that. I wrote down learn, teach, learn. I think that's great and it jives with how I feel as well.
1:35:26 Scott Ingram: Yeah. Yeah. We've covered a ton of ground. I have loved this conversation. Is there anything that we didn't touch on that you were hoping we would would get to.
1:35:36 Megan Labadie: Oh my gosh, we've talked for like 2 hours. Time really flies. No, I mean, I think I'm just super grateful to have had the opportunity to have this conversation with you, to recognize that we are all different, what makes us tick, what helps us learn. I think it's so interesting. So I'm again just grateful to have the opportunity first to have met you, secondly to be sort of put on this platform. I'm grateful for that. And I mean, it's been a great conversation. It's funny when you really dig in with someone to see how many things you've got in common. And I'm just appreciative for this opportunity.
1:36:15 Scott Ingram: Yeah, well, our overlaps are a little bit crazy. I mean, I think we were in the Oracle Marketing Cloud at the same time. So a little bit random there that we came to this place in the roundabout way that we did. I always try and make this actionable for our listener at the very end. So what would you challenge them to do over the course of the next, say, 1 to 2 weeks to improve themselves and improve their results?
1:36:37 Megan Labadie: It's going to be cringy to you people, but record yourself in a meeting and then listen back to that meeting. We record a lot of meetings these days. It's easy to access, but truly go back and listen to a meeting that you led. Watch the faces, see what you're doing, see what you can learn. Try to listen to somebody else's version of it. Again, go back to those recorded conversations. There's nothing I hate more than hearing my own voice on something. I'm sure I'll listen to this and go, ugh. It is just a better way to learn. You can get feedback all day long of what someone thinks of you, but hearing it yourself of what you're saying and how you're coming across and how many times you stumbled over words, and it's going to help you become better.
1:37:17 Scott Ingram: Yeah. And at the end of the day, we are our worst critics. So I can see that working very, very well. Megan, this has been absolutely amazing. Thank you for spending all of this time and sharing your story with us.
1:37:29 Megan Labadie: Yes, my pleasure, Scott. Hopefully you'll edit this so people don't have to listen to me for 2 hours. It's been so great. Again, thank you for the opportunity. And yeah, looking forward to getting to know you more moving forward.
1:37:43 Scott Ingram: Thanks for listening to the Sales Success Stories podcast. To be sure you never miss an episode and for an invitation to our Sales Success Community powered by Influitive, Subscribe to our newsletter at top1.fm.

