103: Jonathan Greenberg - Overachieving at Hubspot Through Attention to Detail, Fear & Self-Awareness

0:00 Scott Ingram: This episode is brought to you thanks to the generous support of Alice, Terryberry, and Vidyard. To learn more about them and all of our sponsors who are supporting this show and this community, click over to top1.fm/sponsors and help me support them in return. You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights Insights and strategies to help you improve. To learn more, visit us at top1.fm. Here's your host, Scott Ingram. Today on the Sales Success Stories podcast, this bonus episode is actually a full interview episode, which means you're gonna get three in a row. And that's thanks to our podcast partnership with HubSpot and Inbound 2020, which starts today. More about the event at inbound.com. And appropriately, I've got Jonathan Greenberg with me today, who is HubSpot's bestseller. So for those who are new to the show, I only interview active quota-carrying individual contributors who are either the outright number one top performers in their companies or at least in the top 1% inside a larger sales organization like HubSpot. Welcome to the show, Jonathan.

1:18 Jonathan Greenberg: Great to be here, Scott. Thanks for having me.

1:20 Scott Ingram: Yeah, really looking forward to digging in. You've sent me some really interesting things in our preview and prep, but why don't we start like we always do with some immediate value? And I'll have you talk about the top 3 things that you believe have contributed the most to your success in sales.

1:36 Jonathan Greenberg: Sure. Yeah. I would say that, you know, just kind of been thinking about this right ahead of the episode. It was actually a great thing for me to do, to be able to kind of consolidate my thoughts. And I think sometimes we just move so quickly in sales, but one of the biggest things I think, and maybe the number one thing for me has just been this concept of attention to detail. I'm sure we'll get into it a little bit more, but in one of my first jobs, it was actually in accounting, working for a CFO whose main mantra, and he would write it all over my desk in sticky notes, was attention to detail. So we'll get into that. The second one, interestingly enough, and maybe oddly enough, but fear to me has been a major motivator. We'll talk a little bit about what I mean by that, but really kind of this, I, in speaking very transparently as somebody who got into sales, not knowing anything about sales and obviously coming from a different financial world, really kind of feeling that raw sense of getting on a cold call and not knowing what to say or not having all the information at hand to win a deal, competitive deal. Fear is a huge one for me. And then the last one, I think maybe ties into that a little bit, but self-awareness, just in really kind of being true to myself and honest about my performance, maybe blocking out some of the adulation, some of the criticism, and really trying to find my own knowing or my own self And ask, you know, hey, how are you really doing? Are you performing to the best of your abilities? Is there anything you can influence? So self-awareness, I would say, is kind of my third there.

3:06 Scott Ingram: And Scott, that's fantastic. This is going to be great. And I'm sure that we'll probably see these show up again, but why don't we start with kind of the attention to detail piece? Where does that show up? I mean, in your day-to-day, where do we see that?

3:20 Jonathan Greenberg: Yeah, I think it meant something a little bit different to me when I was in my first role in accounting than it does now in sales, you know, in 5 years after starting, but It really changed also throughout my career in sales. So started as an SDR at HubSpot, became a BDR, moved into a quota-carrying role after a year, moved a bunch of different divisions, worked in San Francisco, Seattle. So to me, there's always been this kind of concept of change every year and almost like a video game where the rules change a little bit or it gets put on a bit of a different difficulty setting. So for me, really kind of staying closely tied to the things that I do know, You know, what are my metrics? What are the things that are influenceable? Is there a part of my process where maybe I'm running a call every day and I just feel like part of my presentation is off or it doesn't feel authentic or true, or I'm kind of losing people? I used to share a deck that was like 17 slides long. I would lose people by like the 4th slide. So really just kind of keenly paying attention to that. But I think, you know, to answer your question, I think the biggest area of influence it's had for me is in my process. And I think the process piece will kind of… I'll speak about that a little bit separately than running calls or having meetings, but for me, just staying very religious to mapping out my territory, looking at my total addressable market really and saying, okay, you know, here's a kind of zoomed out view of that. Now let me make a really strategic plan to go into that territory, break out what I can and can't do, where I can apply influence. And for me, I'm really looking at it as a full sales year, even though we're on monthly quota. So kind of making that strategy plan or almost like a go-to-market plan for my own territory and staying very, very tight to the details that surround that. That's been really huge for me.

5:07 Scott Ingram: Oh, so much to talk about. So we will come back. We're going to talk about process and planning and how you're thinking about your year and that whole approach. But I'm most curious because you just sent me one bullet in our prep and it just said fear. Tell me about the fear, and and I want to hear how it's changed. Like I can certainly understand the fear early on when you're picking up the call, the phone for the first time, and settling into kind of that rhythm. But I'm really interested in how does that show up today?

5:36 Jonathan Greenberg: Yeah, and I think that like you said, it does. You know, it does definitely change over time, but I think some of the tenets remain the same. And and there's kind of the lower level. Hey, you know, I'm not sure what HubSpot even really is when I first got on a call, and you know, I got out of training. I was like, okay, I think I know, but. I just still have that kind of hesitation. But, you know, really, I think the thing that carries through is the people I was talking to, and I was really trying to contact C-levels. I think what I realized was at the time that I didn't feel that I was on equal footing in my conversations with people like that who had all this experience, who were super knowledgeable about their industry. You know, how could I call them and say, hey, I recommend that you do XYZ? To me, it just didn't logically make sense. And so what I've tried to really use that as a way to become an expert, or as much as I can be, on the industry, on trends, on the market, on some of the things that their customers are asking for or struggling with. And so that has, you know, I think allowed me to not get a sense of complacency if my numbers are doing well, but almost like ignore the numbers altogether and say, okay, If I was sitting in a boardroom having a conversation, would I provide any type of value to these people? If not, let me look inward and try to find out. Obviously not going to be able to make go-to-market decisions for them, but want to be able to actually provide value instead of just saying that. That's one thing I've learned early was salespeople, we've got to provide value. It's got to be relevant. It has to be something that is giving to the customer. And I always kind of questioned that a little bit because I thought, well, at the end of the day, I'm still trying to sell them something. Right. And so as soon as I kind of took that out of it and said, okay, well, maybe I'll lose this deal. You know, maybe I won't, maybe it won't be the right fit, but how can I just have a business conversation and, you know, have a really good, something that that person will walk away from and say, okay, I feel a little bit better after that conversation. I got some insight into a part of the business or the market that we didn't know. And go from there. So that's been huge for me. I think now, instead of that fear of, oh, I don't know something, you know, that's good that they're going to ask me, or I don't know a question that they're going to ask on a call. Now it's been really, okay, how can I provide some value to the people that I'm talking to in those positions of influence?

7:51 Scott Ingram: Jonathan just talked about providing value, being relevant, and giving to the customer. One of our sponsors, Alyce, allows you to do just that. Alyce is a personalized gifting platform that helps you build deeper relationships by creating a personal experience that's relatable, relevant, and respectful through one-to-one gifting. Whether you're looking to open new doors and new relationships or solidify the ones you have, you can learn more about how Alyce is helping enterprise sales, marketing, and customer success teams create personal bonds with everyone they do business with at top1.fm/alyce. That's top1.fm/alyce. Now back to my conversation with Jonathan. There's multiple things I want to talk about there, but let's just keep going because I'll come back to them. Let's talk about the self-awareness piece.

8:43 Jonathan Greenberg: Yeah, I think there's the rigid side of my brain, and I think that that's, you know, my mom was a… she had 9 kids. She got her GED to PhD in under a decade. She was maniacally focused and driven, and I really kind of… I think that that piece of it speaks to more of the attention to detail part. My dad Dropped out of high school, wanted to change the world, and ended up going overseas and doing humanitarian work for 25 years with Mother Teresa, opened halfway houses for youth over there. Really kind of followed his heart. And a big part of what he kind of… the impression he left on me was just, you know, there are a lot of distractions, there are a lot of influences in the world around us, even people that are our friends, our coworkers, you know, people who believe that you should be doing something because of a talent. And to him it was, you know, keep checking in with yourself to say, are you really happy in what you're doing? And at the last business I was at doing accounting at a certain point, you know, that was the trigger for me to get into sales because I was able to stay very true to what I believed. And I knew there was something off. I wasn't really able to use the part of me that liked to connect with people and make connections and have great conversations and be social. I was hiding behind Excel for the most part. So I think that piece of it really helped me, you know, in a zoomed-out way with my role. But then on deals, you know, there's always this part of you that thinks, okay, I heard the customer or the prospect saying XYZ, sounds like, you know, they're really leaning towards HubSpot here. And then something comes out of left field that you didn't, you know, really think about because you just had those happy years. That was one of my biggest challenges when I first started. So I think being self-aware there is kind of the same concept where you could say, hey, what is it that I'm missing? What is it that might be a surprise? And how can I kind of look at past mistakes or deals I've lost and use that as a way to maybe do a little bit more research or prep or find a way to win the next one?

10:39 Scott Ingram: Yeah. I think it's such a recurring theme on this show, and I love that you called it out specifically. I think the best of the best really continue to think of this as a craft, as a profession, and they continue to hone that. But the only way that you can get better at it is you have to be aware enough to know where you can improve, right? What's, what's missing? What's working well that you need to double down on? Those kinds of things. So again, lots to come back to. So why don't we first though put this in perspective? Just talk about what is your role today at HubSpot?

11:12 Jonathan Greenberg: Yeah, so today I cover Seattle for our mid-market team with HubSpot. You mentioned I am the best seller at HubSpot. I'll make a slight caveat to that in saying that There are groups of us who I would consider to be the best. So just to give a small shout out to the team around me, those people are incredible. Right now I'm covering Seattle. I did San Francisco for 3, 4 years, worked at that time in our small business division. So that, Scott, was really working with like high growth businesses, startups, had some really interesting conversations there. And now, yep, it's a little bit bigger businesses. So about 25 to 200 employees. And now downtown Seattle, and this is obviously direct sales. We have a partner side, but I'm on the direct team.

11:52 Scott Ingram: Perfect. And then speaking of kind of the bestseller piece, I mean, put your results in perspective for us. What does it what does it take to be kind of the top of your game over there? Before Jonathan talks about his results, let me tell you about Terryberry, who's all about recognizing and rewarding this type of performance. Recognition drives performance, and Terryberry understands that what gets recognized gets.

12:16 Jonathan Greenberg: Done.

12:16 Scott Ingram: Organizations all over the world have turned to Terryberry and their award-winning 360 recognition platform to recognize people for their contributions towards success. If you understand that a powerful recognition solution can help you drive the success you're looking for, let Terryberry help you build a culture of performance and recognition today. You can learn more at top1.fm/terryberry. Now back to Jonathan and his results.

12:45 Jonathan Greenberg: Well, we have obviously the annual metrics to hit. We're on a monthly quota system. So I think when I first started, that was really where I was focused was, okay, I just got to hit my number. I've got to provide some value to my team. I looked at it as a basketball player. It's like, how can I be the one who's not making the team miss during the month? And now, like, you know, looking at things in a little bit more of a zoomed out way, you know, a lot of our contests and, you know, our kind of annual awards to me, that's really in looking at the way our sale works also. What I've tried to set my mind to is planning for the year. And so 125% or so to hit P Club. And then we have a few other, you know, kind of larger goals for obviously bonuses, accelerators, things like that. But for the last few years, been lucky enough to be, you know, right around 180, 170, 180% for the last couple of years. So really been able to, I think one of the keys has been just, you know, trying to stay as consistent as possible. And again, you know, that those kind of 3 keys I led with there.

13:45 Scott Ingram: Yeah. Well, you said what I was thinking. One of the things I always look for is I'm not really looking to interview folks who hit the sales lottery, right? They got lucky and walked into a great deal and they, it looks like they're a hero, but they can't replicate it, right? Being successful and consistent, strong performer year over year is a super big deal. So you mentioned basketball and I wonder if maybe that'll come into play. Talk us through your origin story. How did you get into sales in the first place, especially from the accounting world?

14:12 Jonathan Greenberg: Yeah, I met a lot of salespeople who have kind of an alternative path to sales. So I wouldn't say that, you know, mine is all too unique, although it's different. My family, well, my dad's from Boston, moved overseas, obviously, as I alluded to, and I grew up in Belgium. So on the back half of his international travels as the 7th out of 9, actually on a little farm. And then when we moved to the States, when I was about 13, so I went to public school in Belgium and my family's Dutch on my mom's side, so I I spoke Flemish in school growing up, which Scott, I can tell you is not a major benefit here in the States. I haven't found too many Flemish speakers in Seattle. We did just buy PieSync, which is great. They're a Belgian company, so I was able to connect with some of those people randomly, but came to the States, ended up on the Cape and went to public high school there, transitioned from homeschooling, which was an interesting transition in the '90s, wearing skinny jeans and really having trouble fitting in. And then I was actually doing a music project with my brothers. We had been trying to record an album and we were doing some performances and shows, did about 300 or so shows in the greater New England area. And really like our mission was to try to provide positive music as an alternative for a lot of young kids out there that didn't have that. And kind of my dad was really helping us drive that. A couple of years after high school, I really wanted to kind of start the next stage in my development. And I was also really interested in basketball. I kind of packed everything into my car. I quit the band. I kind of left my family and ended up going out to Western Mass about 4 hours away and just walking onto the basketball team and starting to study business. And that was a really interesting time for me because I think it finally gave me the opportunity, just like my dad, to kind of branch out on my own and find my own way. I found a really great community there. It took a little bit of time, but found also a way, I think, to learn the very basic concepts of sales, which to me were repetition and detail. And I was learning a brand new sport that was embarrassing, actually. I was afraid to fail in the same way, right? We were 1 and 24 my sophomore year. That's 1 win and 24 losses. And I think that really was when I first said, okay, so this is what's going to drive me to try to become you know, to get to the top of my game, at least where I, as I saw it. I was at a D3 school. I really wanted to go back and play overseas. I was learning business, but at the time, you know, as a sophomore or junior, really didn't know where I wanted to go. Ended up, we had the best record at that school in 25 years. I kind of blew out my knee my senior night. So pretty classic basketball tale. Had an opportunity to go overseas, but the knee really never responded. So ended up moving back to Boston. I waited tables, which was, Pretty bad for a surgically repaired left knee, just going through ACL surgery, but did a bunch of odd jobs until I finally broke through and landed the accounting job over at the Boston Celtics, which was very entry-level, a lot of, you know, kind of basic reporting, doing expense reports, doing department budgeting. And that's really, I think, where I mentioned that attention to detail. I worked for this, one of my favorite mentors, Bill Reisfelder, who's been the CFO over there for 30+ years. And he's the one that left those sticky notes on my desk. Hey, like you submitted a report without a punctuation mark at the end of it. Like he's going to return that to you and you're going to spend an hour going through and looking for other errors. And so I actually rebelled a lot against that. I thought, you know, this is menial stuff. I don't really, you know, I want to do something bigger. Like, can you give me more projects? And I kept asking him, kept, I kept asking him, he refused. And so I was almost ready to go. And I remember we had an operations side there. I was working, part of my role was actually office management that first year. So I went in and I reorganized our whole supply closet. I had an espresso, took me about 4 hours, and he came over and he was like, all right, I think it's time. It's time. You're organized. You're ready to go. And that developed into larger projects, working with our marketing team, working with our customer success team on budgeting and I think there really learned the value of interdepartmental relationships and kind of connecting people to finance and to budget, which really helped in sales. Now, after some time, like I mentioned, I just felt like I wasn't fully fulfilled. I felt like I wasn't really living my true purpose. I wasn't all that excited to go to work every day and heard about a company called HubSpot. A few people there actually mentioned sales as a potential avenue for me. I really didn't want to take a huge pay cut after 4 and a half years and, you know, kind of start something fresh. I met with the president, actually, Rich Gotham over at the Celtics, who had a career in sales, retired young, and they actually pulled him out of retirement to go be with the Celtics. And he said something super influential to me, and that was, you know, you may not kind of know what you want to do, you know, in the future, 5, 10, 15, 20 years from now. What sales provides you is an opportunity to expand that horizon to so many different levels. You're going to get a firsthand look at every department. You're going to be talking to people across every type of business or industry. You know, you'll have a really good sense of what you want to do. And he said sales is one of the toughest jobs. If you can do that, you know, you open up a lot of doors. So I made the jump to HubSpot. I had to start as a BDR/SDR. I was working on a team at the time, I was 28, working with, you know, 5 to 10 21-year-olds. So that was a pretty tough experience, but, you know, kind of battled through that and then got into our small business division working San Francisco and now in Seattle years later.

19:56 Scott Ingram: Amazing. So boy band to basketball, and now here you are selling.

20:00 Jonathan Greenberg: I could have wrapped up that soliloquy, you know, in about 5 seconds with that, Scott. Instead, I took 10 to 12 minutes. So yeah, great overview.

20:09 Scott Ingram: I think it was worth it though. I mean, who knew we were going to connect the dots to the CFO that was sticking sticky notes on your desk was actually the CFO of the Boston Celtics. That's a pretty good story.

20:19 Jonathan Greenberg: Great guy. A great guy too.

20:21 Scott Ingram: Oh, that's great. So if you were starting over today, knowing what you know now, and maybe you're looking forward from your serving job, would you have approached your career any differently?

20:33 Jonathan Greenberg: Yeah, it's a really tough question, you know, because I am one of those people that believes that every experience, you know, helps define you and is a learning moment if you allow it to be, which I know is vague and not the answer you're looking for. But I think if I could do anything over, you know, there was a time at the Celtics where I really didn't practice what I was preaching or what I'm preaching now. You know, I knew that there was something kind of missing in that role. I ended up staying there probably a year and a half or 2 years longer than I should have because I ignored that voice. You know, and I felt like, well, it's just going to get better. It's going to get better. But I wasn't passionate enough about the work I was doing. I think I was more attracted to being around the team and it was an operations side. So we were over at the Garden on game days. I was on the court meeting the players and I think you can get kind of wrapped up into that and lose sight of, well, is this a fun job to do or is this something I could see myself doing for the next 20, 30 years? So I think if I could do it over, definitely go back and just try to apply some of these big concepts to those times in my life, even that basketball journey, starting that 2 years after high school. I think, you know, if I could cut down some of that time, you know, maybe I would have started in sales a little bit earlier, but, you know, all those experiences, especially serving, you know, and working at a restaurant, and I've worked in the restaurant or service industry for 10-odd years, bartended in Boston also for a while. I think that really gave me great, great customer service skills, gives you a lot of patience. Working with 21-year-olds who are, you know, passed out on your bar at 8 PM, night hasn't even kicked off yet. So yeah, I think that there's a lot of things that really helped kind of define my success today that I would not take back. But, you know, if I could apply some of those top 3 to my prior gigs, I think I may have left them a little bit earlier.

22:22 Scott Ingram: Yeah. Well, maybe later you'll have to explain to me the sales learnings that come from having people passed out on your bar at the beginning of the night.

22:29 Jonathan Greenberg: Happy to.

22:30 Scott Ingram: So you told us a great personal story, and I love getting into the origin and just hearing, you know, what informs the path to where we are today. What about a sales story? Is there a particular deal that really stands out for you? Maybe you won, maybe you lost, maybe it was the deal you were scared of, but something that taught you a lot.

22:49 Jonathan Greenberg: I'm gonna focus on success, you know, 'cause I love talking about myself, Scott, in a successful way. But there are plenty of deals that we could spend hours dissecting, and I've already done that, so I don't want to go down that rabbit hole. But no, the one that I think is… there are 2 actually, one being a few years ago, and this was kind of before the Vidyard craze kicked off. And I remember on my team, we were trying to find ways to personalize activity at scale, which is a huge kind of key that I've tried to focus on over the years. And we came across Vidyard. I ended up sending a message to the leader of this pretty high-tech company in San Francisco, and they were growing really quickly. They ended up buying Vidyard for their sales team as a result of that video, which was really kind of a cool thing. And when I went to meet them in the office, it was like, oh, this is the Vidyard guys, the guy that sent us that really personalized video. So I ended up meeting their team and that was kind of a cool win because it felt to me like I work. And as you know, Scott, HubSpot is a big-time inbound marketing company. And a lot of our deals, I'm fortunate to say, like, you know, our marketing team will help influence those. People will come to us, they know the brand. But, you know, as a salesperson at a company also growing that quickly, it's on me to find new opportunities. And I can't, you know, not practice what we preach and go cold call people and, you know, enroll them in mass sequences. So that was really kind of a cool, like, I think kind of creative way to manufacture cold opportunities. So that was a huge win for me.

24:20 Scott Ingram: Well, Jonathan couldn't have possibly set me up any better for my mention of our 3rd and final sponsor of this episode, Vidyard. Vidyard offers a free Chrome plugin that allows you to really easily record videos of yourself, of your screen, or even a combination, and then drop those into your email to really grab someone's attention. Plus, it'll send you a notification when your video has been watched. Give it a try. Did I mention it's free? top1.fm/v for Vidyard will take you right there. Let's get back to Jonathan and his second story.

24:56 Jonathan Greenberg: But I don't know that I learned as much as the second one I'll reference. And this was actually this year during COVID season. I hit a snag with this really big opportunity I was working in. This company does awesome stuff. They're called Greater Good. And what they do is they connect people with causes or charitable causes that they're passionate about helping influence. So you guys check them out. But this company, actually everything kind of stalled. Everything was put on hold with COVID obviously. And At the time, I was working on a pilot with their team, and it's one of the things I've worked on pretty heavily in the last few years is actually almost becoming less of a salesperson and more of an implementation manager as much as I can ahead of the sale. And with a product like HubSpot, there's so much complexity to it that I feel if you can't help somebody visualize their own setup in the system before they buy, it's very difficult for them to kind of take that leap of faith. So this was one of those moments and we, you know, I just spent a few months working with them in a free trial and actually, you know, launching a few campaigns that helped generate some clicks back to their organization that helped raise some money during like a really impactful time for a lot of people. So personally, like, you know, in my, with my background and, you know, the things that I care about focusing on for the future, really want to help give back. So that was a huge win, not just on the deal side, but also to be able to kind of prove that, hey, this concept of putting the deal to the side and just being able to help. And, you know, even if we don't win the deal, let's just try to help this company with what they need to do. I think a lot of people talk about that, but it's very difficult when you're a salesperson, you have the weight of your quota over you. But that's one thing that I've just tried to build into myself is, you know, I might not make my number this month. I might not make it this quarter. But if it's the right thing to do, you know, let's build that connection, that relationship. And, you know, this is a company that ended up being a very quick close once it was all said and done, once they had things greenlighted on their side.

26:54 Scott Ingram: So 2 paths I want to go down based on that. And you mentioned this earlier, I had taken a note that it was essentially disassociating yourself from the outcome and having that business conversation, right? You talked about that really early on. And I think it's powerful. And what you described, I think, is a good story that demonstrates that. That is, you have to find a way to sort of separate yourself from all, I'm in sales, all I care about is closing this deal, because that experience is not very fun for the person on the other side versus the experience that you just described where I'm just trying to help you and maybe I have the solution that's going to help you, but even if I don't, we're going to find some way to provide some value and get you pointed in a good direction. I'm just going to let you talk more about about that? Because it sounds like you figured out a way to kind of make that transition and do that really well.

27:46 Jonathan Greenberg: Well, I think it ties into the fear piece we were talking about a little bit before, where it's, you know, like, what am I able to actually provide? You know, like, okay, I'm a salesperson. I get on a call with you, Scott, I'm trying to sell you something. Like, we know that relationship, or we know that dynamic ahead of time, ahead of the call. So really, that's like the uphill battle I'm fighting when I first start to talk to somebody is Well, they don't really technically believe that I'm just there to provide value and to help them out, right? Like, well, at the end of the day, this guy's a salesperson. Okay. So I think that that's where I've really tried to lean into, okay, like, you know, what is the thing that all salespeople have that is unique? Personally, I feel that for me, at least in my role at HubSpot, I'm talking to hundreds of companies in the same verticals, in the same industry or employee employee size. And so if I'm doing my homework and if I'm looking at trends across those conversations, I actually do have something really unique to provide to those CEOs or C-levels. I can say, hey, without naming names, like, here's a few things that I've seen where other companies just like yours are finding success because they're doing XYZ, and here's a few things where they're, you know, they're dropping by the wayside. And those are things that if I didn't have those conversations with all of those people, I think that's something very difficult for a CEO to go find online or very expensive to hire a research firm to do. So I think approaching the conversation like that, with just a genuine interest and curiosity about the business makeup, thinking about it as if I'm an investor or board member, I think that's always started the conversation off on the right foot. And then it kind of gets to, okay, well, now we've reached like kind of an agreement on what we believe is the path forward, but Jonathan, You know, we worked with larger orgs that shall remain nameless that are massive companies that have been around for a long time and they promised us XYZ and, you know, here we are a year later, we haven't implemented things. And so if my, you know, my real big themes or my pitch around HubSpot is this kind of time to set up and how can we simplify a lot of things that are too complex. So I want to prove that out as well and that's really what I've tried to do. It's not so much that I'm going to go in and do all of the implementation work that a consultant or that our great onboarding team might do, but just to say, hey, like, let me show you a few of the things that I'm telling you so that you can also confirm with logic and reason that this might be the right solution going forward. And I think you get to that stage by building some trust in that initial conversation, you know, with some of the information you might have about the industry or things you've researched.

30:26 Scott Ingram: Yeah, that's great, great, great stuff. And I appreciate you setting me up earlier for the Vidyard mention, a great sponsor of this show. So that was perfect. But one of the things that you mentioned in that was that you really love this idea of personalization at scale. Talk more about that, because this is also something I'm obsessed with. So what does that look like today?

30:46 Jonathan Greenberg: Yeah, so I think that this all came about as a, as a BDR and an SDR where my numbers really related more to the number of meetings I was booking. And obviously, the deals that were closing did have some influence on it. But You're in that role, it's kind of like, hey, go out and find good quality conversations. And if I'm a BDR manager, like, I'm gonna set that number pretty high, right? Because we have a pretty fast-growing team. So there were a few ways that I saw other people around me that were relatively successful that were, you know, coming in at 5 o'clock in the morning and hitting the phones and doing 100, 200 dials a day. Others were, you know, doing things like mail merges or You know, sending out a bunch of kind of cold emails at scale and hitting 100, 200 activities. And really as a BDR, I was kind of put on this activity board, right? Watching like, how many calls are you making? How many emails? I didn't have the credibility to say like, hey, Mr. Manager, like all of my emails are really personalized. I know I'm last in activity, but you know, these are great. It's great stuff here. Check these out. So what I tried to do is say, okay, I'm going to Do a little bit of both. I'm gonna start off, I'm gonna try some of the things that seem to be working for other people. I'm also gonna spend the extra weekend coming up with some more creative messaging or doing that little bit of extra research and building that into my process, like really helped because it was the creative messaging. It was that, you know, 5-5-5 rule I heard on a similar… heard somebody talking about this recently, 5 minutes of research, 5 minutes to write the email. 5 minutes to look up something about the person that you're sending that email to. And I love that because that to me came off as a real valuable message to somebody. And as a BDR, that helped. Those were the deals that seemed to be closing. As a rep, I kind of took that and said, okay, now I need to also, on top of all of that activity I'm trying to put out, now I need to like also close deals and run calls. And there's just this extra weight now in terms of my time during the day. So it's now even more critical than ever to do that type of personalization at scale. And that's when I got into Vidyard, started getting into things like CloudApp, where I'll record like a small GIF of a part of the product or something that a theme or a concept that we're talking about. I've used Doodly before, which is a kind of like a whiteboard animated video creator. So things like that, I find those to really like the first step for me is just get somebody's attention. Let them know that that email is not spam, that there might be something of value there. But then the message, keep the message real short and personalized, pitch the meeting, which is really where I'm going to be doing, you know, most of the talking or the figuring out if they're even a good prospect and if we're a good solution for them.

33:29 Scott Ingram: So I think I know the answer to this. It's probably pretty obvious, but if you had to choose one path versus the other in terms of essentially quality over quantity, right? Like which path do you choose and why? And does it only work for you in the way that you're doing it, or have you seen other approaches? Work just as well? Because I'm sure you've seen a lot of different people do a lot of different things across HubSpot.

33:51 Jonathan Greenberg: No, I think that's a really good question because I think that it plays out based on the individual, right? So my authentic self, like, I don't love having 5 seconds on the phone to pitch somebody on my product or service and book a meeting. But there are other people who, like, that is their innate personality. They are very, very good at that. And that's, you know, kind of, I think, their top skill. For me, like, my… I believe that my skill is being able to do that research really quickly, be able to identify what a challenge might be, and then put together some creative writing around that. Actually used to be a… I used to think that I would be a fiction writer, Scott, at some point wanted to write stories. So a lot of that writing I think is kind of just my, that's my skillset. And so I lean heavily on that. Those people that are making high activity dials during the day, I think that that's also a skill. The one thing I haven't seen pay off that successfully is blasting people with cold messages and cold emails. That seems to be consistent across every salesperson I've talked to. But I think for me now, it's almost like a little bit of a mixture between both because as I develop relationships with my prospects or as, you know, if they eventually become customers, what I'll try to do, and, you know, we have this concept of additional products that they might be purchasing into on the customer side. And so once I've kind of built that relationship, what I'll try to do is also some of that activity in larger increments, meaning last year, for instance, I ran a webinar for all of my current customers that were using a specific product that showcased some value of a different product that they weren't using. And in that type of situation, I was able to do, you know, kind of a mass invite to those people. I'd already kind of built that trust. They knew who I was. It was really more about using the tools at my disposal. To be able to get those invites out a lot faster, ended up getting 40, 50 people to sign up for kind of a mini webinar that I ran on my own. So a little bit of that kind of mass activity in certain bursts or with the right people, I think is useful. But if I'm hunting that new deals or if I'm trying to develop brand new relationships, I think it's super important for me to start that relationship on the right foot. Yeah.

36:00 Scott Ingram: Good stuff. I'm glad I asked. So you have accomplished a lot. You've had a lot of consistent success, what are you most proud of?

36:08 Jonathan Greenberg: It's gotta be the boy band days, Scott. Being able to perform, doing choreography in front of, you know, my middle school peers and then having the stones, for lack of a better word, to go face them in high school the following year. I'd say that's one. On the sales side though, I think that, you know, we talked about this or alluded to it a little bit in the beginning, but consistency, you know, and I wouldn't even say, and I've listened to a bunch of these podcasts and heard some really good sellers who've been around for a long time. You know, I've been in the game for 5 years or so. So even in a small sample size, looking at HubSpot and the way that things change, the way that my role has even changed over the years and the products I'm selling have changed, to me, I'm most proud of just being able to come in year in, year out, have a plan, try to execute that plan, obviously hit snags and potholes throughout, but seemingly, you know, continue to have success even with new rules, new products, and new changes every year.

37:03 Scott Ingram: Nice. Now, I didn't find any videos of your boy band days, but I know there's a video or two of you singing the national anthem at a Celtics game. So maybe we'll stick that into the show notes. And if you have an old boy band video for me, maybe we'll link that up too.

37:19 Jonathan Greenberg: There's a reason, Scott, we've scrubbed everything. No, it was thankfully pre-YouTube days. So there was… and pre, like, cell phone capture. So there was… the videos that are out there are actually VHS tapes.

37:31 Scott Ingram: Wow. Some things belong in the past, right?

37:34 Jonathan Greenberg: They do. They do. But once we digitize it, I will get you a copy of that and it'll be a good laugh. It'll be a good laugh. There you go.

37:41 Scott Ingram: Fantastic. Well, the other thing that we haven't shared is you're not a little guy.

37:45 Jonathan Greenberg: In stature, I am 6'7. We were just talking about the new puppy and how I had to match my stature to my puppy, which I actually did not need to do, but it was a, was a requirement I set out. And now I have an Old English Sheepdog that will be 100 pounds in under a year.

38:00 Scott Ingram: Unreal. Unreal. I don't know what that says about me. For those who've been following along for a long time, you know that I had a Chiweenie. Unfortunately, we lost her a few weeks ago. So we have a new rescue pup who she just lacks the weenie. She's just a Chihuahua and she is 7 pounds. So I don't know what that says about me. I don't think I'm that small, but she's a, she's a little bitty thing.

38:21 Jonathan Greenberg: It's part of my, you know, trying to bite off more than I could probably chew. Scott, I'm noticing a pattern, but I'm going to have to figure this one out because I want to keep my house under relative control. We need some law and order.

38:31 Scott Ingram: That's right. So, well, that's a pretty good transition, right? In terms of, you know, whether it's biting off more than you can chew. I'm just curious about what's the biggest challenge for you these days? What do you struggle with the most?

38:43 Jonathan Greenberg: Yeah, I mean, I think that as I've progressed at HubSpot, you know, you kind of… one of the things that's great is that you keep all of your customers. So anybody who I've sold to, you know, they're going to continue to be relationships of mine that I'm going to develop over the years and You know, I'm kind of always looking at things as like, okay, well, what did I do last year for deal creation? And should I continue to stay on that pace? And you try to factor in all of the different avenues, you know, with existing customer upsells or net new. And I just think that having the rules kind of change every year and having things be a little bit different, that's been difficult. It's been difficult for me to maintain the same levels of activity that I've had in years past. You know, I have more kind of customer conversations or I want to help somebody out with a project they're working on. It doesn't necessarily relate to MRR. So really, like, I think kind of keeping control of my calendar and trying to stay true to the things that I know I need to do, but still being like self-aware enough to say, okay, you know, maybe I can be okay with dropping my deal creation rate a little bit as long as my ASP improves this year. Or maybe I can find a way to improve a small part of my competitive talk track so that I can win a few more of those deals. So I think not being too closely tied to the numbers, which is, I think, an accounting trait of mine to constantly be auditing and saying, okay, am I exactly at this metric? Okay, I did this over the last 3 quarters, so that must mean that Q4 is going to be that. There's a lot of nuance, I think, also to our sales process. And as a company that's breaking into new markets, you have to kind of allow a little bit of flexibility with yourself to not hold yourself too, too tight to the way that you've done things before. So I think I sometimes will fall into that rut or routine, and there's a benefit to that because it keeps me really organized and process-driven. But there's also, you know, a part of that where I need to kind of pick my head up sometimes and say, okay, am I putting in the most high-quality activities for what I need for this moment? Am I holding myself to the right metrics? And then, like I said at the very beginning, like, am I still even excited and nerdy enough about this product to want to learn it every day and to learn new things in the industry? So I think those are some of the things that I've struggled with and just trying to keep myself aware of nowadays.

41:05 Scott Ingram: Yeah. Well, let's talk about the routine and the process and all of those things. And the way I usually start this, we've, you've listened to a few episodes, you kind of know the drill. I like to walk through kind of a typical day in the life, but starting at the very beginning. So alarm goes off, what time does that happen? And just walk us through until your head hits the pillow.

41:25 Jonathan Greenberg: Yep. Life is a lot different nowadays with a puppy. So actually that is my alarm. It's him barking or growling usually around 5. We've stretched it now to 5:30 AM. It's been great. I tell myself because I've been able to do a little early morning prospecting, but For the most part, I'm getting up and really trying to focus on kind of physical, mental wellbeing, at least for the first 30 minutes to an hour of the day. I love coffee. I love consuming information about my territory. So I'd say that I was listening to Lisa last week and she just had these amazing books that she's… I think she said she was reading for 2 hours every morning. Like unbelievable. I wish I could get to that level. For me, like my main focus again, back to like, okay, what's my focus for this year? It's really understanding my territory. And so I'm deep in like GeekWire and Puget Sound Business Journal and the Seattle Times and a lot of local news to try to pick up anything about businesses there, or even just like some commonalities I can talk to people about on the phone. So first thing is, you know, kind of reading the paper, having my morning cup of coffee, and then I try to get a workout in as soon as I'm kind of awake enough to do that. I'm a big wellness fanatic. I've switched my diet over. I went to a carnivore-only diet for about a year. I've now since included some vegetables, which my girlfriend's very happy about. And after that point, it's kind of like into my workday. One of the things I really love about living on the East Coast and working in West Coast territory is that my calls don't… I don't talk to a human until, you know, 11 or 12 the day. So I have a great prospecting block in that first part. And I'll usually do my admin, my sourcing, you know, go through my LinkedIn and see if there's any major changes that I need to be aware of. Job changes are a huge one that I'm tracking. And then usually 12 on is kind of my calls, my demos, you know, anything else that I'm doing. Mondays I've been blocking off as almost like a full prospecting and admin day. So I try not to take any meetings at all. If I can on Mondays. I've been doing that now for about 2 or 3 months. And I would say I have like a 50% hit rate on a day with no meetings or not, but I love starting the week off that way. That gives me a much more organized feel. I feel like my actions are much more intentional. And then at the end of the day, usually just kind of winding down, trying to make a plan for the following day, do follow-up emails, et cetera. And, you know, walk the puppy.

43:54 Scott Ingram: Nice. Let's zoom out a little bit because you talked about You've got a monthly quota, but you're really focused on kind of the big picture and thinking about things annually. How are you doing that planning, that preparation? When are you thinking about that stuff from a, you know, kind of higher level perspective?

44:13 Jonathan Greenberg: Well, I think that there needs to be just like a business plan. There need to be regular check-ins throughout the year. You know, if it's going to be an annual plan, what I try to do is we have our quarterly business reviews. So like that's already kind of built in as a time for me to say, okay, how am I performing against the goals I've set for this year? And during that time, one of the things I really love about HubSpot is we have a big focus on wellness as well. So it's not just, you know, how's your ASP this quarter? It's how are you feeling toward, you know, with the stress and the grind of the day-to-day sales job? So I think that's been kind of a big thing to just have automatically built in. And then my Sunday nights are really like my time to say, okay, like, what do I need to do? What part of the month is it? Because there is some timing to that as well. Even though I'm looking at things annually, a lot of times there might be deals that need to close at a certain time. And so I'm usually prioritizing by, you know, first is any deals I have in play or things I need to kind of push across. Is there any next step for me to do, or am I waiting on somebody else? And then, you know, what are the prospecting activities that are going to determine the best results for that week or for that month? So say Sunday nights are kind of my strategy nights. And then I have kind of my quarterly check-ins as well to see how I'm doing from a more like zoomed out perspective.

45:31 Scott Ingram: Got it. Let's come back to the wellness and I'm hoping I can even get into the mental health side of things as we start to get ready for the Sales Success Summit this year. That's an area that I kind of committed to going pretty deep into because, and this was before COVID I think it's probably even more important now. I mean, you were talking about some of your cabin fever and we just have different issues. I mean, I've hardly been out of my house in months and months and months. This is, this is a different experience. And I think a lot of us struggled in different ways before. So how are you managing that, whether it be mindset or mental health or all of the above? How do you think about that stuff?

46:11 Jonathan Greenberg: Well, it comes down to, for me at least, that self-awareness, right? So first is, okay, am I on the right track? And I'm so kind of like process-oriented and I need to have everything kind of detailed out. So I'll break it out into my top categories, right? There's my family, there's my work. I know that those are 2 big things I want to lean on. There's my personal life. I love playing basketball. I love playing guitar. I do yoga, meditation. Like some of those things are, I just kind of feel like I need to do that once a week or once every other week in order to stay happy doing what I want to do. So there's kind of like the larger categories that I look at and I want to check in with myself and say, you know, how am I doing? Is there My mom actually has this rating system in her mind for her 9 kids where she has like a green, yellow, red. She's like, okay, son number 7, you know, he's got a big test coming up. He's in the yellow. Oh, son number 8 needs some help with his credit. Like he's a red, you know? So I kind of try to think about that with those categories also and just say, okay, I've really been grinding for the last 3 months with COVID you know, worrying about my quota and worrying if that's going to impact, you know, deals I have in play. Okay, now I really need to focus on, you know, the physical well-being side of me, or, you know, pay attention to some of the things that have helped me kind of relax or de-stress in the past. So that's really kind of what I'm looking at is those larger categories and, and how I'm doing every day towards those.

47:33 Scott Ingram: So do you get other like pipeline management sort of strategies from your mom? I guess I'd never considered… I mean, I have 2 daughters and that's it. I can't even begin to wrap my head around 9. So I assume you have to come up with coping techniques and you, you color code your children. Are there other things that sort of come from that? That's, that's insane.

47:54 Jonathan Greenberg: Oh, absolutely. You know, we had to be pretty self-sufficient because my parents were working a lot too. So they assigned, you know, group leaders and those leaders were in charge of kind of assigning different roles and responsibilities to other people. So we, you know, we had to learn this concept of responsibility pretty early. Even though I don't know how well I did towards it, but the concepts were there at least. But I think like one of the biggest things I've learned from my mom is just that sense of like, you know, the work's never really done. She says this thing all the time. She's like, if you're walking from one place to another in the house, like you should be carrying something because if you're not, like, that's another thing you got to do later. And so it wasn't a like, oh my, you know, like there are so many things to do that We just don't have time to do them. It's like, there are things to do. And if we do them, we're going to get, we're going to get to where we need to be. So let's get on it and let's do it. And I think that's why she was able to do so many of these kinds of things that I think I take almost for granted because I've talked about my story a bunch, but you know, they're kind of these huge life things, especially getting her degree and coming over from Europe with no GED. She ended up going to Yale and being the first nurse practitioner through their PhD program there after, you know, just a decade in the States. So. I think the biggest thing I learned from her is that drive. It's like, if you want something, sit down, map it out, go after it. And then of course, some of the organizational benefits and seeing how she managed the crew of us, 8 boys and 1 girl, by the way. So there was a lot of energy in the household. Wow. Wow. Wow.

49:24 Scott Ingram: Let's keep going on the drive kind of side of things. And I'm curious to know, does the fear come back into this? Fear one of those drivers? Like when you just think about motivation in general and what gets you to do what you do, what is it?

49:39 Jonathan Greenberg: Well, I think it to me is because I think that answer is different for everyone. To me, it's an ever-changing thing. It started as fear for sure, because it was like, well, okay, I can't get to where I want to be if I'm losing deals or if I don't know XYZ. But I think what I really needed to do is change that to be a more positive motivator. And to me, that eventually became, well, I want to have a farm someday. You know, I want to have a place for little Cosmo to be able to herd some sheep around. So, okay, if I know that's my end goal, you know, how can I work myself backwards into the numbers to try to get there? There's some personal and professional things I also want to accomplish. I want to run a business. You know, I want to eventually go and play in the Maccabee Games, which is about 3 years from now. So I want to get my knee up to that point. So I think like having a few of those more positive goals has helped me say, okay, like I'm going to use that fear as a motivator because if I don't do these things, I won't get to that goal. But the end motivator is really the goal instead of the fear. And I think that helps me kind of put a more positive spin on it and say, well, yeah, I have to do 12 hours of sourcing today to find some great accounts. By the end of the day, it's going to be worth it because I have that shining light to look forward to instead of just the fear of losing or not closing enough MRR.

50:57 Scott Ingram: Yep. Yep. Where does the self-awareness piece come into play? Like, is that a practice? Is that a specific process? Or is it more just ingrained and incorporated into what you do? How do you think about that?

51:10 Jonathan Greenberg: Yeah, I think it's something that becomes ingrained in you over time if you give it enough thought, or at least for me, that's been my experience. There was a time when I kind of just I said, okay, I need to do XYZ. And I just put my head down and barreled through it. And I really didn't realize after, like I said, at the Celtics after 3 years, that that wasn't really what I wanted to do. And I kind of needed to have that built in so that I would hear the warning signs. So now I have these kind of like regular check-ins with myself as almost second nature, but it's because I think I really tried to spend the time after the Celtics to say, okay, am I repeating the mistakes of the past? Am I actually happy with what I'm doing, or, you know, is there something better out there for me, or something that could give me more life, more purpose? If you have that one thing, and that's why I always ask anybody who says, hey, like, I'm super excited in HubSpot, really want to get into sales, it looks awesome, like, well, what's your driving motivator? You know, what's your thing? It could be money for some people. It's been money for me, you know, where I had to kind of work my way out of the poverty line and, you know, get to a place where I could hopefully buy that farm someday. But I think there's a, like I said, it kind of has to be that like larger goal, that bigger vision. And if you have that, I think then it's pretty easy to check in with yourself and say, okay, am I still working towards that? But definitely important at a certain part of my life, I didn't really have the focus on that. So if you feel that you haven't spent enough time, you know, kind of truly trying to decide, and this is tough, Scott, because, you know, when I was an entry-level salesperson, I wasn't I was just trying to get by. I was trying to keep my job. I wasn't thinking like, well, like, you know, if I wanted to do this, then I should be, you know, if I wanted to go paint, I should go start art school now. You know, I was really just like focused on the task at hand. So I think it's a developing process too. Like as you continue in your career or in sales, wherever you are, you'll find things that might be more interesting to you or not. So if you could build in that little sense of self-awareness, I think those things will pop up. Louder on your screen, interrupt your day, so to speak, in your mind and help keep you kind of focused towards that true north, that like happiness level.

53:19 Scott Ingram: Yeah. Do you find that you do it with each of your deals? Do you kind of take that time to process the wins, the losses, and learn at that level as well?

53:30 Jonathan Greenberg: Yeah, I know it's a good segue into kind of the sales part of self-awareness. And I think that is so critical on every deal, even still after 5 years, like We haven't, we've changed our products, but you know, there are some things that are absolutely crucial to know in every conversation. And most of my conversations, I try to keep as unstructured as possible because I really want it to be more of a genuine conversation versus, you know, hey, we need XYZ piece of information from you, or this isn't going to work. So I think in those types of conversations, you can sometimes miss, you know, key or critical things. And I really work with my manager a bunch on this. Is like, okay, what did I hear that you didn't hear? Or what did you hear that I didn't hear? I think that's where kind of group selling comes in, where different avenues, different thought processes can really help. So yeah, it's super important. And one thing that I keep in mind on every deal is, you know, what are some of the things that I might be missing or not thinking about that could derail this thing?

54:26 Scott Ingram: This feels very meta right now because I feel like, wait, isn't that what I'm doing? Right? I want to try and just have as real and authentic a conversation as we can. But at the same time, there's certain points that I want to kind of get and have that perspective because we've gotten that perspective from so many. But I'm really curious about what are those most key critical items for you, right? If you think about those conversations, what are the top things that you feel like if I don't get this, it's going to hurt me later in my process?

54:55 Jonathan Greenberg: Well, it seems like oversimplified to say like, you know, in the same way that somebody might have a motivation for why they would put 12 hours into sourcing on LinkedIn. Like, somebody's got to have a motivation to buy HubSpot or to look at HubSpot as a solution. And we can get distracted, or I get distracted, I've been distracted by some problem that arises maybe in the conversation or something that they might be really focused on, but that isn't the reason that they would buy the software or not buy the software. So for me, it's like, okay, There's a lot of nuance to the sale. There's a lot of really, really important information that I need about budget and timeline and all the kind of standard sales stuff. But if I don't know what the motivator is for that specific person and what's going to help them in their job or their role, then I'm really kind of lost. And so that's my biggest key now is like looking at things as less of an account-based selling type of model. Or really more role-based selling. This is something that a good friend and mentor of mine, Ryan Mansman, who works with me and I have talked a lot about is, you know, what are those specific motivators for that individual? How can I help them build out a plan towards that? And then let's figure out, you know, how this also directly impacts the business. If it's something that solves for both, you probably have a pretty good opportunity. If it's one or the other, That's where some of those red flags pop up and that's where I need to dig in a little bit more.

56:24 Scott Ingram: Man, it took us an hour, but I feel like that right there, at least for me, is such a gold nugget. And I'm flashing back to the conversation that you mentioned earlier, the conversation that I had with Lisa. And I feel like maybe this wasn't even in the actual episode. Maybe this was, was part of the secret track, but what we were talking about was the emotions behind the deal and we buy emotionally. And yet I feel like we as sellers, I as a seller, am really not good enough at getting to the core to you. And I think you said it really well, essentially, like, what's the why behind this deal? Like, why does this person, not this company, because we can do all the logical justification all we want, but if there's not that emotional, why does this person want to make this change and make this investment? If we're, if we can't get to that, it's so much harder. And if you can get to that, it's so much easier.

57:21 Jonathan Greenberg: Yeah. And I think it could get pretty distracting because people don't necessarily want to open up about that because usually what they're trying to solve is a business problem that just happens to affect their department or their role. And it's kind of for them. And I remember this from being in my accounting role, you know, I looked at QuickBooks, we had to do an ERP evaluation. It was like, okay, my boss told me to do an ERP evaluation, so I'm doing it. You know, and there are some things that maybe this software could help me with or, you know, help me in my job. But at the end of the day, it's just a software and I'm going to go to work and put my 8 hours in and go home. And so I think like, it's almost our job as sellers to help people get to that place where it's like, okay, well, how can this actually impact your day-to-day? And is there something here that, you know, could help swing that person emotionally? If not, that's fine too, because that just might be the case for that deal, but I'm going to forecast it a bit differently also. Knowing that. So I think that that's been really key to work on and try to keep in the back of my mind. And then also it's really helped in moving into kind of selling to bigger businesses and having more stakeholders involved, you know, an average of 4 or 5 people now in the sales process. I mean, getting buy-in from each of those people and really trying to understand their intrinsic motivations as well. That I think helps put the whole package together for now a CEO to say, okay, this is how it's going to impact Bob and here's how it's going to impact Scott. And he's able to go to them and have a conversation with them and see that truth. So I think that's been huge.

58:49 Scott Ingram: Well, and you went exactly where I wanted to go. So how are you doing that when, when you're in a more complex multi-stakeholder deal like that? How are you getting to multiple individual whys?

59:01 Jonathan Greenberg: Well, I think I'm in a little bit of a unique position selling to, you know, not like the 5,000-person orgs in the world, but a lot of times even a mid-market company, 200 employees, let's say they have 5 people on the marketing team and you know, a 50-person sales org, a lot of times, like, those people that I'm talking to are pretty connected with somebody in a different department. You know, they know their motivations. They may not know the emotional motivation, but they know kind of the business motivation. And that is really just the trigger that I need to get a conversation with them in order to get that kind of emotional side. So for me, it's really, you know, how can I provide enough value for the first person I talk to? Build that trust, like I mentioned in the beginning, you know, be kind of a market researcher for them, give them some info they might not have, then build out some trust in actually showing them how the solution might impact their specific role. And from there saying, okay, like, hey, we're able to help you. Like, is there anyone else we can help here? And I think, you know, asking them a little bit questions that are a little bit less tailored around like, okay, well, how does this impact your sales team? And saying, okay, well, Greg leads sales over there. And what are some of the things that he asked you to help him with this year? You know, and looking for that kind of alignment or, or maybe even breakage in the trust between departments. Figuring that out has helped a lot and just getting those intros from one person to another. Yeah.

1:00:27 Scott Ingram: Good stuff. Great tangent. So we talked a little bit earlier about in your morning, you're doing a lot of reading and what I heard there was it's very focused on kind of the Seattle market that you're selling to, right? So just getting inside the heads of, okay, these are, these are my business owners there and what they're going to be thinking about and what's on their horizon. What else makes up your information diet? What are you reading, listening to, and watching? And when all does that happen?

1:00:56 Jonathan Greenberg: Yeah. So I'd say that most of my kind of like personal information digesting, digesting process, I don't know, we'll come up with a better term for that. That happens on the weekends actually. And I really look forward to that time. Being able to kind of go into things that are not specifically related to sales and just kind of take my mind off of everything for a little while until Sunday, at least. So I personally have always been very interested in kind of this new wave of holistic healing and wellness and looking at the body as an interconnected and integrated being. And so I've really been studying a lot of that. My girlfriend's actually studying Eastern medicine and going through her acupuncture program now. A 3-year master's degree. So she's been poking me with needles and that's been really interesting as well. But I just recently read this book, Proof of Heaven, which a lot of people know about a neuroscientist's post-death or near-death experience. Really fascinating kind of scientific and non-scientific story just about, you know, kind of understanding your purpose in the world. The latest one I've been reading is actually The Art of Raising a Puppy. I don't really need to say much more there. And then some of my sales books that I actually wrote down, Lisa's Future of Leadership in the Age of AI. I actually ordered that book right when she mentioned it. That sounds super interesting. And then I've been on Audible. I use Audible a bunch. I've been getting through Gap Selling and Start with Why and The Unfair Advantage, like some of those pretty classic sales books. I love Duane Larkin. So those are kind of, I think that I try to, you know, not just only fill my mind. I respect Alyce because she is just the most incredible reading habits and standards. What I try to do is, you know, keep my focus on things that are also fulfilling or, you know, kind of fill my spirit with joy on the non-sales side as well.

1:02:46 Scott Ingram: Yeah. You mentioned that, you know, Lisa's reading habit is sort of next level. I think there's a lot of things about Lisa that are next level, actually. What's on my… I'm probably halfway through in my Audible listening to the other book she recommended called Multipliers, which is just a fascinating, great, great listen in my case. So certainly enjoying that. Let's kind of keep going on that thread, especially like along the sales books and things of that nature. Do you subscribe to a particular sales philosophy?

1:03:14 Jonathan Greenberg: Yeah, it's a really interesting question. And timing-wise, it's a really interesting one too, because right now at HubSpot, we're all going through our Sandler training, which I had already done a few years back, but really great to get a refresher on that. And I actually kind of grew up, or grew up, but you know, when I first started in sales 5 years ago with the Challenger framework. So I guess like as an outsider or as somebody who's always considered themselves a little bit of a sales outsider, you know, still being a bit of a rookie, I'm always thinking about these different kinds of philosophies. And I think Sandler, I would kind of sum it up as like Sandler is a great structure and framework for a sales process and Challenger is kind of like what the style is that you run, but at the end of the day, like it's ultimately up to you to kind of weave both of those into your authentic voice. And I think when I first started and I was really trying to stick myself into a sales framework or a sales process, it really came off almost disingenuous and my questions came off robotic and it wasn't natural at all. So I think like you said about our conversation today, it's like there are some themes that are really, really important that I can get as part of the, or that I can highlight as part of the sales process. I really want to make sure that I get those themes through, but how I go about getting those themes through, I think, is what is, what makes up kind of the art of selling, right? And so that's something I'm still working on and improving is making sure that I'm not just having a one-off conversation, that I'm still applying some of those core themes. But it's something that I really think is important is staying true to your authentic voice while still having, you know, that sales, that process and that framework in mind. Yeah.

1:05:02 Scott Ingram: I mean, that was so well said. I think that's ultimately what it comes down to. I mean, we talked at the beginning about, you know, you have to be a student of the process and treat this as a craft and as a profession. And there's no, I don't think there's an out-of-the-box approach or process that's just going to work because to your point, it's going to sound like somebody else. It's going to sound robotic. It's just not going to work. But you have to figure out a way to really own it. And you talked also about your process was really key to your success. What is your process then?

1:05:35 Jonathan Greenberg: How much time do you have, Scott?

1:05:38 Scott Ingram: These can go pretty long, but I, at some point I do need to get to my next meeting.

1:05:42 Jonathan Greenberg: No, I get very excited about process. I think it's the regimented mind of my mom coming through in my physical body. But when I started as an SDR and BDR, I was like, okay, so they're teaching me this way to go about doing activity and here's how I approach conversations on the phone. And then I got some Challenger Sale training through my first manager selling deals in our small business vertical. And over time, with that kind of sense of accounting, I think I was really looking at it and trying to audit and say, okay, well, what is working? What's not working? Where can I make improvements? The biggest improvement I needed to make was how can I get my activity higher? While still personalizing it. And so to me, that meant really like cleanly mapping out my territory, my opportunity. Like here's at the very beginning of the year, all of the available companies that I could potentially talk to this year. Now let me break those down by priority using things that relate to, again, the role, the people that I'm selling to, you know, are they coming up? Do they have an account that's coming up on a competitive renewal? Or did they just announce some funding or they just changed their whole marketing team? So that's kind of how I start by mapping things out in the territories based on timing on behalf of the people I'm selling to. And then zooming into that, it's okay, well, what are the daily activities that I can do to influence that process? What's my deal creation look like? How am I moving deals along? Is there part of my, like, even my demo process where You know, there's a concept that's not getting through. How can I work on that? So for me, process means all of the different stages of a sale that you can potentially influence. Is there something that you can do to influence that in a either to speed up the time to sale or you know to improve your close or win rates? And I was really struggling for a while with even presenting HubSpot because we have a kind of like a website page that we go to and. Everybody talks through the inbound methodology and for some people that works really well, but I felt there was like these larger components. Like we weren't talking about our services, our onboarding team, which is like a huge part of what we do. We don't outsource any of our consulting. Like we hand deliver somebody who's used to setting things up like this. So what I wanted to do is build a deck that showed, you know, kind of some of the top 3 reasons why people buy and just a small thing like that. Like it led to other spider webs within my process to say, oh, my like demo portal, I need to fix this and that there because, you know, here's a part where my demo's going off the rails. Long-winded way of saying, like, I think to me, my process and to other people, everybody has a bit of a different process. But if you could be really critical about, again, those influenceable moments on behalf of the seller, is there any part where you can improve? That to me is kind of what I'm looking for all the time with my own process.

1:08:35 Scott Ingram: Love it. I would love to go deeper down this rabbit hole, but I I actually do need to manage time a little bit better than I normally do. So that's my fault. I do block a good chunk of time to get through these, but even still, sometimes it's not quite enough. So we may have to circle back on the deeper dive in some of the nitty-gritty of the process and the style.

1:08:56 Jonathan Greenberg: But, you know, we can, we could potentially talk about that at the Sales Summit, Scott.

1:08:59 Scott Ingram: There we go. There we go. Well, more to come. There will be some interesting opportunities going on there. Well, there's a couple of questions I always like to ask just to, I don't know, I oftentimes create sort of a soapbox moment. And the first one is, is there something you believe that the average sales professional would think is crazy?

1:09:20 Jonathan Greenberg: Well, I think eating meat only for a year is probably what I'd lead with since most of my friends and colleagues did think I was crazy, although it did help with my digestive system considerably. But I'm not gonna say that as my kind of core, you know, here's the crazy thing. I think personally, like there's this really interesting new trend towards LinkedIn as the modern business card. And I truly, truly believe that that is really important. And maybe this isn't a direct answer to the question because a lot of reps do believe this as well, but I think that I have come across a lot of reps that still even now today believe that social selling's a waste of time. And again, it depends on kind of your, you know, are you selling transactional? Are you selling enterprise? I don't know that I have directly influenced a lot of deals with the content that I produce on LinkedIn. You know, I'm not getting people inbounding to me and say, hey, like we're ready to buy HubSpot Enterprise today. But I think that the LinkedIn profile should not be a resume. And I see a lot of sellers at HubSpot even putting their attainment percentage and how much ARR they sold, which is great. Like if you're looking for other opportunities. But I think having that be your kind of pillar that you send your prospects and customers to as a way for them to get to know you better and say, okay, this person knows what they're talking about in the industry, or they're posting relevant information, you know, they're able to get to that place of trust a little bit faster. So maybe not too crazy, but I think it's crazy that people don't, haven't leaned in fully. So we'll go with that one.

1:10:52 Scott Ingram: Yeah. Yeah.

1:10:52 Jonathan Greenberg: Gosh.

1:10:53 Scott Ingram: I mean, that's a topic that has been a personal obsession of mine this last year. And I mean, I've always been a big proponent of LinkedIn and used it heavily, but, you know, really kind of upped my game starting late last year. And the project I've been working on the better part of the year, if you're not familiar with it, the LinkedIn Sales Stars project. So if you go to top1.fm/LISS for LinkedIn Sales Stars, we've been tracking the top 100 folks that are in sales that are driving the highest levels of engagement. And Jonathan, you're obviously doing a good job. You came up onto my radar. Just before we did the last evaluation and, and made that list. And I think a lot of the things that you're doing matter. And I think that specifically what you talked about in terms of this needs to be more buyer-centric, not job-centric, right? Because if done right, it's really about positioning this for your customers and building credibility. And what you said to me when I let you know, like, hey, you made the list, And you said, that's great. I'm not going to post about this because it's not why or how I use LinkedIn. And I think just having that understanding of what you're doing was… I totally respect that.

1:12:06 Jonathan Greenberg: Well, I definitely appreciated the nod, Scott. And I was hoping that that message didn't come across offensive because I think that, like, I love the network. I think that… and I went through and followed a bunch of people on that list and I'm watching kind of how they're doing content. Some of these people are just at an incredible level. Of awareness for what I think their buyers or prospects are looking for. It's a small but a big community, the sales community, I'm realizing, and there's some really good people to lean on in that network specifically. So I really love being kind of able to get into that and to meet some of these people from other businesses because again, I'm all about getting perspective from the rest of the industry so that I can kind of widen my scope and be more in tune to what's going on, not just with HubSpot and not just with my buyers, but also with the rest of the industry and how things are. And then my last point there, Scott, really interesting also, I think, is the makeup of your LinkedIn. So your followers are the people that you have in your network. And when I first started, it was like, okay, I'm going to follow all of my friends and hopefully they tag me in some things. I want to make sure I kind of broaden out my network. I'm gonna go follow some influencers as well. What I've tried to do is like go and find the best people in marketing automation or in demand generation and watch what they post and the information that's interesting to them so I can kind of become, you know, a little bit more centered in their world. But I think it's… that's what's amazing about LinkedIn. You know, if you have a good mix of, you know, the people in your own direct sales network, you know, those top LinkedIn sales stars that are publishing this great content to emulate. You also have a great group of the people that you're actually selling to. And then, you know, kind of a third layer of these kind of top-line influencers. I think it's really important to kind of audit that and say, you know, what does my LinkedIn makeup look like? Do I have the right people around me to help kind of expand my scope?

1:14:06 Scott Ingram: Yeah, absolutely. I think that, you know, it's kind of that peer thing, right? So if you're connected to a lot of the people that influence your buyers, right? That says something, right? When they look at you and they're like, oh, I have these common connections and oh wow, those common connections are people that I trust and have some relationship with. And, you know, it just, it lends more and more credibility.

1:14:28 Jonathan Greenberg: Yeah. And there's even some really good groups you can find too. I found a few really good like marketing automation and, you know, customer kind of centric groups where you have to go through a little bit of an application process. And obviously I can't, you know, go in there and spout the good word of HubSpot or I'll get kicked out. But just like scrolling through that in the morning, you know, I find that even to be more valuable than going through GeekWire and looking at the latest funding. Like I can go in and see if somebody is upset with a competitor or, you know, they've found some new kind of demand gen formula that seems to be working. So I find those groups to also be really valuable.

1:15:03 Scott Ingram: Yeah. Great, great stuff. So I want to ask the flip side of my question that kind of kicked this off. And that is, is there something the average sales professional believes that you think is crazy?

1:15:14 Jonathan Greenberg: Well, I think that that would depend on what the average sales professional is like. Are we talking about, you know, the 60 to 80 percenters? We're talking about, you know, the 80 to 100. But like, for me, I personally feel that there's kind of a split between like the top 25% of salespeople are all doing something. And I think the one theme I've noticed, even if it's a small business seller or an enterprise seller, and from listening to a bunch of your podcasts and a bunch of different types of content, The biggest thing to me is creativity. I see a lot of that and, you know, kind of like being able to think for themselves, whereas there's more of a robot mentality with a large other kind of swath of people. So for me, like, I guess I understand, I think it's crazy, but I guess I understand the craziness a little bit in that a lot of people will come and say, okay, like what's the formula for your success? Like what is the script that you follow or what's your prospecting playbook? Or what are the templates that you've been sending out that, you know, you're starting to book meetings from? And it's a very difficult concept to get through because I remember that when I was in that seat where I was like, okay, if somebody could just give me a few of the steps, then I can come up with the creative angle on my own once I kind of get into the flow of it. So I think like if there was a way to begin sales training without this kind of regimented or rigid, you know, we need to do XYZ according to this process, according to this framework. And if we could build in that creativity from the beginning to say, hey, at some point you're gonna graduate from, you know, just doing the standard steps in that process, and it's gonna be on you to develop your art, to develop your, you know, your music, right? And to say, okay, like, here is how your voice is translating this process that we're giving you. And so that's one thing I've always been a little bit, I've always like I've gotten into a few head-butting conversations with some of the sales trainers in my career, you know, because I think that some of that authenticity is grayed out a little bit because we know what we can get if somebody hits 100 activities a day. We know what we can get if they hit XYZ deals created. So it's, you know, it's okay. Well, where's the faith in the actual person that you hired to go out there and kind of, you know, come up with their own creative formula for that? So I think that's my long-winded way of saying like, there's no formula, I think, or like set model. I think a lot of people sadly believe that when they first get started. Lean into your authentic voice and, you know, obviously take process and meld that together. I think that's kind of the key for me.

1:17:45 Scott Ingram: I happen to know that you're wearing a headset and this would be very difficult, but I feel like you can sort of drop the mic right now. That for me is so spot on. And I think you're right. Like everybody's looking for Just give me the answer, give me the playbook, give me the set of actions that I can take that every time they're going to work. And it doesn't work that way. It doesn't work very effectively that way. And those who are the best, it is the creativity, it's the self-awareness and understanding this is who I am and these are the types of things that I can say in the ways that I can say them that maybe if Scott tried to say those same things, He would sound like an idiot. It just, it wouldn't be authentic. And I think the reason this is such a challenge in this industry is because that's hard, right? It takes work and practice and it's on the individual. And I can't just give you, this is the order of operations. If you do this, you're going to be successful. I mean, I keep going back to You know, I look at marathon training plans and man, they just work. You know, if you'll spend these, whatever it is, 12, 16 weeks and follow this process and do all of these workouts, you'll be able to run a marathon.

1:19:05 Jonathan Greenberg: Right.

1:19:06 Scott Ingram: But there's not that thing in sales. Yes, there is a lot of science pieces to this, but there's also a lot of art. And until you kind of work through and do the work on yourself Nor do I think any of us want to be automatons. Like, if you wanted that, then you would have stayed in finance.

1:19:28 Jonathan Greenberg: Yeah, I think that for me, it became pretty clear when I was learning… well, when I was thinking about music, because it took me a while to learn how to play guitar. It took me… like, we did vocal coaching. We actually did choreography lessons 4 to 6 hours a day for a few years. I think… I don't know where that went because I think I've lost most of that, but It wasn't until like I learned how to actually play the guitar and sing that I could then write a song on my own. And it wasn't the greatest song, but I was able to kind of put my own spin, my own authentic spin on it. And I wasn't able to do that if I didn't have the fundamentals, the base. Same thing with basketball. I wasn't able to go out and be a top performer without knowing how to shoot a free throw or do a left-handed layup. I had to build in some of those fundamentals, but I think it's when you reach that inflection point where it's like you push the bird out of the nest, it's like, okay, go fly now. Like it's on, I think that training side or whatever, that kind of beginning part of the sales process or training process to say, we're gonna teach you these fundamentals, but as you're going through these fundamentals, start to think about how they could apply to you as an authentic individual. You know, and I think like telling your story is a great way to do that for people who are looking for ways to kind of practice that true authentic self. It's like, tell somebody about yourself at the beginning of a call, just a short overview, and it will feel way more natural to start to kind of sell in that same way instead of, you know, when I first started, it was like, hey Scott, where are you calling from? What's the weather there? Oh yeah, great. Okay. Well, HubSpot Enterprise, you know, it's like a very awkward transition. It doesn't even come off as, you know, a real conversation. But yeah, I think that that art of selling that Lisa mentioned on your last podcast, a lot of people talk about that. It's difficult to quantify. Like you said, it's a very tough thing. It's something that I know that even when I'm done selling, I won't be at the top of my game. It's something I'm always kind of improving and working on. But just like anything else, you do have to have the fundamentals still built in so you're not missing some of the key components.

1:21:33 Scott Ingram: Yep. So that's maybe the best setup ever for me to ask What advice you would give to somebody that's just starting out in their sales career today?

1:21:41 Jonathan Greenberg: Great question. I think that personally, first things first, like if the industry that you are selling in or the product that you're selling, if you are not interested in that product or industry, it is going to be an uphill climb for you. You might be able to get away with it for a little while, kind of manufacturing that excitement. And again, like, you know, I sell marketing software. I'm not. As excited about that as I am playing with my sheepdog, but there's a lot of really, really interesting things about the customer space that excite me. I love looking at financials and understanding growth statements and figuring out business problems. So it's intrinsic to me to do the research because I know that that's going to help me in my conversations, but it's also kind of interesting for me to learn about new technology and new things that are popping up. So One, I would say really try to figure out something that aligns with a concept or a topic that you're interested in. I would be prepared to go to bootcamp, I call it, you know, the first few years of sales, as with anything, you're really kind of figuring out your place. You're figuring out like what it all means. What is it? And I think it's a higher, or it's a longer ramp time than a lot of other gigs where, you know, like we were just talking about, it's very regimented. And in accounting, if I did XYZ and I ran my reports this way and way I was gonna be, you know, I was gonna perform my job functions. I was gonna get paid for it. In sales, it's like, okay, well, I gotta learn the fundamentals, but then I also have to learn how to creatively practice my art. And so the uptime or the ramp time for that takes a little bit longer. If you're prepared to go through that and put the work in, I think it's super rewarding. And, you know, with that in mind, obviously, like keeping that end vision then clear in your mind, I think helps get you through those tougher times when you're really figuring things out. So super important, I think, just to have that self-awareness for that larger goal and then apply that to something that you're really, really interested in.

1:23:40 Scott Ingram: Yeah, great, great stuff. And I love the boot camp piece of that too, right? I think there's just sort of a recognition of the first period of time, it's going to be hard. You're just, you're not going to know what you're doing. You're going to be uncomfortable. It's not going to feel right. You know, there's just so… mentally, it's going to be really, really challenging. And I think if you prepare yourself for that, right, if you're going to be a Navy SEAL and, you know, you know, you're going to have to go through something pretty awful to get there, it's going to help to do some training for that and some mental preparation and just know this is going to be really, really hard. And I don't want to ring the bell.

1:24:19 Jonathan Greenberg: Yeah. In your conversations with other sellers on this podcast, like, how do people approach that? Because I found that it's different you know, in those moments to say, okay, I know what I'm getting out of this. Like, I know it's going to be really tough, but when you're in that valley, I can say from personal experience, I've been in many sales valleys and I'm like, man, it's, you know, it's a grind. Like I missed my number or I didn't hit this quarter or, you know, I don't think I'm going to make club or whatever. Like, have you seen a common theme there with other sellers as ways to kind of pull themselves out of that?

1:24:51 Scott Ingram: Ultimately, I think it really does come down to the mindset piece.

1:24:54 Jonathan Greenberg: Right?

1:24:54 Scott Ingram: You have to go in and know that it's going to be challenging and there's going to be really low points. And I think it's just being committed to the process and it's like learning anything, right? You're not going to be good when you start. The getting good comes from practice and repetition and trying things and falling on your face and getting punched in the face and all the other things that are going on there. I mean, the other analogy I like to use is, you know, it's kind of like if you want to be a doctor and you want to go to med school, there's gonna be a weed-out class, right? There's gonna be some chemistry class or something that is designed to make most people quit. And I don't know that sales is designed to make most people quit in the beginning, but I think it's the reality. I think the first couple of years, they're just freaking tough. But if you can get through it, man, the other side is amazing. Right? I mean, the earnings, the opportunities. I mean, you can go anywhere. I mean, to go back to the story you told in the beginning with the president of the Celtics, the foundation that you can build in sales, if you can get through that, you can literally go anywhere, do virtually anything.

1:26:10 Jonathan Greenberg: Yeah. And I think it's hard to also know, like, am I in the right situation for that? You know, or at least continually audit because you know, a lot of friends across the industry who were in bad sales situations and it was like, well, I'm just going to keep, you know, I'm in a valley. I'm just going to keep plugging along and eventually things will turn around. It's like, if you could be self-aware, even to like your place at a company and say, okay, like this isn't the right opportunity for me. I need to open something else up here rather than, you know, kind of butting your head against the wall. That I also think is like, to your point, it's like, it's not something that is built in to weed people out, but there are things that will come up that will weed people out. And I found that at HubSpot to be the case for sure with, you know, all of our products constantly changing and, you know, people switching territories. And there's a lot of different parts to it, but I think, yeah, keeping that self-awareness in mind to say, yep, like I'm in a valley right now, but no, I know that there's a path here for me. Or, you know, hey, I need to be brutally honest about this and maybe kind of change my environment. That I think is really kind of crucial there.

1:27:20 Scott Ingram: Yeah. And I think you're absolutely right. And I think it's one of the big reasons why developing some type of network or community… I mean, it's the reason why I work so hard in sort of developing the Sales Success Community, because some of those things you just can't go this alone. Right? You have got to figure out how to develop some mentors and some people within the organization, but also outside the organization, because there's also plenty of really, really toxic, horrible sales places that are not representative of what sales is and should be. And so I think a lot of times it helps to get some of that outside perspective and have somebody that's been down this road and seen different things who can say, yeah, actually, Jonathan, You're in a horrible situation. Like, this isn't you. You're just in the wrong spot. We got to get you into a better spot where it makes sense to do that work and to slog away because you are just sprinting at a wall, at a dam. I mean, that thing's never going to move. So knock it off. Let's, let's get you pointed in a more productive direction. So I really do think you've got to be mindful of having some outside perspective, right? Self-awareness is super important. But the rest of getting that awareness is having people who are looking at you from the outside pointing out the blind spots and the things that you may not be able to see from where you're standing.

1:28:43 Jonathan Greenberg: I totally agree. I think it is tough for newer sellers to develop those relationships with people who might really know those things. You know, like when I was first starting out, I didn't want to go follow all the, you know, the VP of sales at Drift and Klaviyo and some of the other big tech companies. But also I was like, well, I don't know, like, are they going to want to connect with me? Like, I'm just a lowly sales guy. But that's why I think it's really great to have something like what you're building with this network of people just like us who just are experiencing different things at different places and could say, oh, actually, this is my experience at XYZ company and this is my experience selling enterprise versus small biz. I think that helps ramp up newer sellers a lot faster, at least in that understanding of what's out there. And that, I think, in turn, like you said, helps with self-awareness to say, like, am I in the right spot or not?

1:29:34 Scott Ingram: Yep.

1:29:35 Jonathan Greenberg: Yep.

1:29:35 Scott Ingram: And it's, you know, the reason as, as we get pretty dang close, as, as we release this to the 2020 Sales Success Summit, there is going to be a ton of networking time. So we've invested in a platform that's going to allow for a lot of conversation and a lot of networking and a lot of that to happen so that people can develop those relationships and develop that network and have people That they can reach out to who can give them some of that perspective. So let's go a little bit further in. So we've talked about advice for somebody that's just getting started. What about somebody that's further in, right? Maybe they've made it through the weed out period. They've they've made it through a couple of years. They understand the fundamentals, and maybe they're good, but they're not great. What advice do you have for them to help them break through to that next level?

1:30:19 Jonathan Greenberg: Yeah, well, I think it's an interesting place to be because. The first thing I would ask is like, do you want to be great or are you happy with what you're doing? Because, and there's nothing wrong with that. There's a lot of people who are not making club every year, but they have a great job and they like what they're doing. And it's like, okay, well, like you're meeting with me because you want to understand the secret sauce to try to find a shortcut to get there, but you're really actually kind of happy with where you're at. If something better came along that you could do easily, Then, you know, that's great. You'll hear it. But for the people that I think are really, really driven to continue to climb, and I loved the analogy that Lisa gave last episode about a career kind of jungle gym instead of a ladder. I feel like that applies to sales in a lot of ways as well, because it's not a direct ascension. You know, you're kind of like, okay, well, let me meet with my sales engineer once a week to try to understand the product better. And that's going to be really tough because it's going to take away from my prospecting time. It actually may hurt my number this month, but in 6 months, that's going to help me close bigger deals. I'm not going to need to get an engineer on a call for some technical conversations. So I think like that actually was one of the keys for me as I finally kind of picked my head up and said, okay, I think I kind of understand the process. I feel pretty confident in what I'm doing. Like, how can I now get to the next level? It was really trying to become a student of the product and cut down on my sale time and improve my close rates by learning some of the things that our engineering team really was brought into a lot of conversations on. So I'd say that, and like, you know, looking at your sales pitch, like, does it feel like it's getting monotonous? Are you reinventing yourself at all? Are you changing in any way? And again, like this could have nothing to do with your success. It's not like, oh, I'm failing and I need to quickly shift my pitch, but it's, you know, people can kind of hear this in your tone on the phone. I believe they can hear your excitement for what you're selling, you know, your passion, and that translates into how true they believe it to be or not. And so I think even small tweaks here and there can kind of freshen you up with our monotonous days nowadays, running 10, you know, however many meetings on Zoom all the time. I think for an average or for a seller who's kind of been doing it for a while, it can just kind of feel like you're going through the motions. So even changing something up there, I've tried to do that every quarter, every couple quarters, and that's really helped. And then how are you working with other departments? I have tried to really kind of weave myself into other departments here because there's a lot of departments that are looking for direct sales feedback, and it's really beneficial to our product team, for instance, for them to have a conversation with me and say, hey, like, why are we losing deals in this product line? Or where can we make some small improvements that are going to help with rep adoption on the sales line, for instance? So I found that a lot of people, you know, in our busy days, it's very difficult to put the time aside to do that and kind of give without getting something in return. But what it's opened me up to is this, like, much better understanding of how our whole team works together, you know, what new product advancements might be coming down the line that I obviously can't sell ahead of time, but, you know, just having that knowledge is going to help me make a better recommendation. On the marketing team, like I've been included in a few webinars and I tried to help them with a few different campaigns and, you know, they've helped me give me some, you know, great talk tracks for people that I'm selling to and I'm basically selling to the people on the teams that I'm then helping inside HubSpot. So I think just working with a few different departments, even if it's not, you know, the direct sales org, trying to give of yourself freely, even though we don't have the time, you know, strategically. But I think that that can really help you expand your understanding of the organization. And like you said, Scott, you know, build that internal network as well to help, you know, give you a little bit more context for your conversations.

1:34:22 Scott Ingram: Yeah, great. Great stuff, man. This is pretty unusual because I really do a better job of scheduling these so we can talk as long as you want, which probably drives… I guess the people that are listening right now, like, they love it because here they are, you know, whatever it is, 90 minutes or more into the episode. You know, the folks that it irritates are the people who've already left that where I go close to 2 hours. But today we're a little bit time constrained.

1:34:46 Jonathan Greenberg: So for… we appreciate all of you. Yeah.

1:34:49 Scott Ingram: So for everybody's benefit, I really try and always wrap this up. With something actionable. So what would you challenge our listener to do, Jonathan, over the course of the next 1 or 2 weeks… 1 week this time because we'll have another interview next week… to improve themselves and improve their results?

1:35:05 Jonathan Greenberg: I'm going to stay with the accounting theme. So my accounting theme is audit everything. And it doesn't sound as horrible as the standard audit might be. But, you know, if you've got those categories in your personal life, your family, your work, you know, your personal relationships, your wellness, Whatever those things are that are really important to you, you know, continue to check in with yourself and you may have to block off an hour to do, you know, that side project that you wanted to do when your work might get in the way, but you just have to do it because you're going to burn out if you don't. I think that has been huge for me and just kind of continuing my consistency. So I don't get that real bad burnout that I used to get early in my career. And then in terms of like your actual sales process. I think the only person that can really critically look at and understand if there's improvement to be made. Your manager can to some extent, you know, your VPs can look at your numbers, your manager's obviously listening to your calls or might not be, but you're really the one who's kind of that market research, that strategist again, right? I'm looking at trends across the conversations I'm having with business owners and saying, okay, here's some of the things I'm seeing or not seeing. Like, I want to apply that also to my own process. And to my own activities every day. So, you know, am I looking at my deals that I've lost and trying to find or learn something from them? Am I looking at my actions I took the week before, the month before? Is it taking me forever to write a follow-up email that I can templatize or whatever that little thing is? If you can continue to keep a watchful eye on it, back to my core theme of self-awareness, I think that will really bode well for you in improving your process as you go.

1:36:44 Scott Ingram: Great stuff, Jonathan. Thank you so much for your time and being so open with me and everyone. Everybody that's listening. This has been fantastic.

1:36:51 Jonathan Greenberg: Thanks for having me, Scott. Great to be here and great to connect with all the sales professionals in your network.

1:36:58 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.