96: Breaking Records During a Pandemic - Outreach's Top Enterprise SDR Kyle Hermann

0:08 Scott Ingram: You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve. To learn more, visit us at top1.fm. Here's your host, Scott Ingram.

0:24 Scott Ingram: Today on the Sales Success Stories podcast, my guest is Kyle Hermann, who is the top senior enterprise sales development representative at Outreach. And it's worth noting, because I realized in a conversation earlier today that I don't really say this on the podcast, but I only interview quota-carrying individual contributors who are either the number one top performer in their organization or at least in the top 1%. So that's why Kyle's here with me today. Welcome to the show, Kyle.

0:53 Kyle Hermann: Appreciate it, Scott. Thanks for having me. Excited for what's in store here.

0:56 Scott Ingram: Absolutely. Well, let's, let's kick things off like we always do with some immediate value and talk about the top 3 things that you believe have contributed the most to your success as an SDR?

1:06 Kyle Hermann: Yeah, yeah, that's a great question. And for me, I'd say there are 3 things that stand out the most. First off, I think it's extremely important, and one thing that SDRs that are new in their role, what they don't tend to do is ask a lot of questions and be curious about the role. They get shy, scared, think they're being a nuisance at times, which I get. And there's some point where You do have to be self-sufficient. But I think asking questions is important because if you don't, stuff gets unanswered and it slips through the cracks at the end of the day. And it's funny enough that I actually still joke about this with the first manager I had over at Outreach, and we talk about it all the time. He's like, man, when you started, you asked way too many questions and it was annoying. But now looking back at it, I really do see the value that And why you did that, because I'm looking at my reps now and they see this, you know, they see the same thing and they're afraid. They're afraid to ask questions and really dive into what they need help with. So with you being so vocal about it, you know, it was able to give him a better understanding of where I needed help and how to be successful on those ends. So I think, again, being curious, ask any questions, whatever's top of mind for you, it's important to get those answered. So that you can maximize your results.

2:24 Scott Ingram: And does that carry over to the way that you are when you're talking with prospects?

2:30 Kyle Hermann: Yeah, that's a great question. I 100% think so because it gives you this mindset that you're not just curious about how to be successful as an SDR, but you transition that in that you're curious about how businesses are operating, how businesses are run, and it gets you in this mindset to poke around, ask questions, find the value, find the pain. And ultimately, at the end of the day, you know, we're here to help and solve a problem. So I think that that definitely is relevant when going through and actually going about your day-to-day prospecting skills.

3:00 Scott Ingram: Yeah. And, you know, I think it's interesting. I had another conversation earlier today with another gentleman who, you know, much more experienced and senior, and he's in a spot where he's, he's doing a lot more cold calling. He's like, Scott, I haven't, I haven't made cold calls in a long time. But he says, all I do is I just, I just try and get them to talk. Right. And if you ask a good question and engage in a conversation, he's like, it's amazing how much they'll tell you.

3:24 Kyle Hermann: Yeah, it really is. And, you know, I try to stress this and teach the newer folks that join the SDR team and the ones that I help onboard as well. And I'm always trying to stress, ask open-ended questions because you're going to get them talking. And once you get them talking, you're going to find a pain or you're going to find something that's bothering them. So at the end of the day, what that comes down to is you just needing to align that pain with what value you can add and how you can help solve that problem. Yeah.

3:53 Scott Ingram: Great stuff. All right. So the first one was ask a lot of questions and be curious. What's number 2?

3:58 Kyle Hermann: Yeah. The second thing for me would be the training and coaching that I got along the way as an SDR. I can't be more thankful for the way things worked out with my sales development coaches here at Outreach. And each of them complemented each other in different ways, which was super unique. When I first started, I had a manager, his name was Ken. And what Ken really specialized with and what he really helped was getting you comfortable with the uncomfortable. So for that, for a lot of folks that come in new into a sales gig or new into an SDR gig, they're not comfortable on the phones and it's one of the most uncomfortable situations to be in. So Ken really drilled that into me. He made sure that whether I sounded good or not, I was comfortable to pick up the phone and make a call. And at the same time, also being able to handle objections, being able to do things that you just have to do at some point, even though they might seem a little weird or seem a little quirky or uncomfortable. So he really did a fantastic job of drilling that into my day-to-day, especially working with the people who are ramping up to full quota. I think that was a perfect complement at that time. And then transitioning from there, I then moved on to the SMB team where I worked with Dylan Fletcher, who was my second manager. And what Dylan did a fantastic job of was really honing into your skillset, figuring out what you were good at, and then helping you play to those strengths. And then at the same time, finding out what your weaknesses were and improving those. So really making you become an all well-rounded SDR. So at the time for me, I would say my biggest issues were I was not a great email writer. I didn't know what I was doing with when I would LinkedIn prospect and just finding other ways to break in and be strategic and methodical and then take that approach. And I was just a big call-heavy guy, but Dylan really helped me iron out my weaknesses. And then at the same time, still get my call numbers up, my conversion, call conversion rates up. So I was still improving every day. And really, that's where I skyrocketed and broke through in my SDR career when I was on Dylan's team. And I would say he's by far the best sales development coach I've ever had. And then more recently, I moved on to the enterprise team about 7 months ago, and I've been working under Heather Burke, who's my current manager right now. And what she does a really good job of is career growth and figuring out what you want to do next and ensuring that you get there. You know, she's been in the business for a while. She was an account executive herself, transitioned into sales development, and is really good at just understanding what your career goals are, understanding where you sit right now, how to leverage and, you know, really push yourself to make the jump for whatever that may be.

6:48 Scott Ingram: That's awesome. And I love hearing about organizations like this where they really are growing their people. I think I shared a sales tip a number of months ago where I talked about, I think in a lot of ways the SDR role is a career trap for a variety of reasons. And the only way out of it is you've got to find an organization like yours where everyone's invested in let's develop our people and get them to where they want to be, whether that's they want to be an AE or they want to lead a team or whatever that path is for them. So, I love hearing these stories where there's this much development opportunity and growth opportunity involved. And obviously, you've thrived. We're going to certainly come back to kind of some of those inflection points and what it was that you learned where it really started to click and you really felt like you got it. But we've only done 2 of the top 3. So what's number 3?

7:37 Kyle Hermann: Yeah, I know these are longer answers, but I feel like everything's pretty valuable here. And then for me, the third part was, and I think this is arguably one of the most important things, was mimicking and really picking the brain of the top performing rep at the time. So when I came in, I had some friends who had already been in some sales roles. This was my first job out of college. So wide-eyed, don't really know how things operate. And what I did was before I started, I asked one of my friends, I said, hey, what do you think I should do to solidify myself and be successful in an SDR role? And he said, figure out who the top performer is and pick his brain. So at the time, the top performer at Outreach was a guy by the name of Alec Kimball. Since then, Alex actually moved on to an account executive role with Outreach as well. But Alex was a killer, great on the phones. And I will never forget this for the rest of my life, but the first day I came into the office, I went up to Alex and I said, what do you do? How do you do it? And I'll never forget, he said, get good on the phones. So from that day, my main focus when I started was to learn the script, learn the value props, learn how to understand how organizations are run and structured. And from there, you know, it really, it really did measures. And I put time on Alex's calendar just about every week. We met with one-on-ones. I shadowed his best practices, replicated his workflows, and then he helped me set personal goals and really get me to where I wanted to be and served as a fantastic mentor and helped me really build my brand over at Outreach.

9:12 Scott Ingram: That's awesome. And yeah, kind of what this show is, is all about, right, is allowing folks to hear from the top performers in a variety of different ways. And I very recently built a list and we'll add your episode to this list as soon as we release it. But if you go to top1.fm/sdr, I just put all the SDR episodes there on one single page. So if you are an SDR or you're an aspiring SDR or you want to be a great SDR, gosh, there's probably a dozen SDR-focused interviews on that, on that page at this point. So really great stuff if you're enjoying this conversation. With Kyle, there are lots more. So Kyle, let's, let's put this in perspective a bit. Just talk about kind of what your role is and the current role, right, in this enterprise SDR role that you're in. And just talk a little bit about Outreach for anybody that isn't already familiar, but hopefully they're all already familiar.

10:03 Kyle Hermann: Yeah. Yeah. Great question. So yeah, to start out. So right now I'm working as the senior enterprise SDR here at Outreach. And what that entails is being a part of the enterprise team where primarily targeting companies who are 2,000 employees plus. So essentially going after the big fish, hunting after the big fish, and bringing in the larger pipeline opportunities for the company. And being in the senior role with that now, I'm still a full quota-carrying individual. So I'm still doing my day-to-day SDR prospecting and breaking into different accounts. But at the same time, now I've taken on some more responsibilities on the management side and doing a lot of training and onboarding for our new enterprise hires. We do a week of bootcamp, do a lot of workflow shadows, call practice. As many enterprise and SDRs know, in general, breaking into the enterprise space is a lot more difficult. You have to be methodical. You have to really grasp on the personalization and make it relevant because everyone wants to do business with the big fish. And I think it's really important to hone in on your skills and take everything that you've learned and then level up and be a pro. So we do that throughout our enterprise bootcamp, teach them how to be successful in the enterprise space. And then from there, you know, I do Gong call practices, call reviews with them. So essentially go through their calls and see what they could do better and what they could improve on. And maybe they're already doing something well, so we'll highlight all that. And then serve as almost like a secondary manager to my current manager and basically serve whatever she might need and help the onboarders through the day-to-day struggles, the stuff that comes their way, the questions they may have, and basically be as a resource to help answer those questions. So that's in a nutshell what I'm currently doing at Outreach. And then to answer your question about Outreach, essentially what we are is a sales engagement platform. And ultimately the goal is to help sales reps be more efficient with their day-to-day optimizing, prioritizing workflow, and putting them essentially into a sequence or a series of touchpoints to drive engagement from either potential or existing customers. So perfect.

12:14 Scott Ingram: And then quantify your results for us. I mean, just put this in perspective and what does it take to be number 1 at Outreach?

12:20 Kyle Hermann: Yeah. So we're scored and graded on sales accepted leads. So essentially what we're doing as SDRs is we're doing a lot of outbound prospecting. And then from there, the goal is to book meetings for our account executives who, after the first meeting, if it goes well, they essentially accept that lead into their pipeline and it creates an opportunity. And that's what we're scored on. So over my time in my last year, I've attained about a 200% quota attainment. And actually in April, I broke the enterprise sales record, which was 22 sales in a month. And that ultimately sourced close to $700,000 in pipeline. So it was crazy how that worked being in the middle of COVID and everything that was going on, but things kind of just clicked then and worked out pretty well.

13:07 Scott Ingram: Congrats. That's fantastic.

13:09 Kyle Hermann: Appreciate that.

13:09 Scott Ingram: So you said this is your first job out of college. Why this? What brought you to sales?

13:14 Kyle Hermann: It's interesting. I mean, what got me really passionate about sales is, I mean, it started with my dad ultimately. My dad used to sell insurance back in the day. And he always stressed to me, he said, one of these days you want to work for yourself. And essentially you can do that in sales, right? You're at that point where your work, the time you put in, the effort that you put in, it directly relates to the end result and you reap the benefits of how much time and effort you put into your day-to-day. And he even said, he said, it's a grind mentally every day. Like he was, one foot in, one foot out the door. And essentially that's how you feel as an SDR. The highs are the highs and the lows are the lows. It's pretty tough if you're having a bad day as an SDR, but at the end of the day, you're facing rejection, you're facing tough times. It's hard to get people to want to take a meeting with you, but just having that it factor and not wanting to quit or being persistent with your day-to-day and doing whatever it takes to get to that end goal. And I saw that with him and that really inspired me to start a career in that. And then just throughout my time in college and, you know, learning from some of the people that I looked up to who were a little bit older than me, who got their career started in sales, you know, I looked at their lifestyles and what, you know, what they do and what makes them successful. And I modeled myself after them and wanted to be something like that as well. So nice. That's where I stand.

14:40 Scott Ingram: Let's talk about like that mentality piece. I mean, how are you managing that?

14:44 Kyle Hermann: Yeah, it's tough. I mean, it's tough to be in a role where you, the majority of your day, you face rejection. And it took me a while to figure it out myself. But what I like to do, and I try to stress this onto the people around me as well, is I think you got to go into each call, each situation with a fresh slate, fresh mindset, because the minute you carry a bad call over, the next call is going to be bad as well. People can read off your energy, read off the negativity. So every call that I make or every time I'm engaging with a potential or existing customer, I'm trying to stay positive, high energy, come in with necessary personalization along with some sort of human aspect to it, like adding the humanity, the empathy. I think all of that is extremely important. And just ensuring that you don't carry over the negative, the bad aspects within your… you let that go, short-minded. And I think that stemmed from me playing sports as a kid and you lose a game and 2 days later you're back to the next. So my dad used to say, flush it down the toilet, get rid of it. Yeah.

15:56 Scott Ingram: Is there something that you're doing before each call to just kind of reset the mindset and make sure you've got that positivity going forward and such?

16:05 Kyle Hermann: You know, I think at this point it's just, it's kind of muscle memory for me. I think when I first started it was tough to really gain a grasp on that because it's so easy to let yourself get into a lull and, you know, things spiral down. So I think just when I was having those issues, it more so came from, I think just honestly like separating everything apart and looking into each Prospect is a totally different opportunity in a different situation. And just reassuring myself that I was going to go into each call and book a meeting.

16:40 Scott Ingram: What about the longer mental cycles? Right. So what about if you have an off day or an off week? How are you recovering from that?

16:47 Kyle Hermann: Yeah. Yeah. I think as far as the longer mental cycles, the tough months, the tough weeks, it just comes. I think it's just the same thing. It's all, it's mental. If you think of it, If you think you're gonna go into the next week with a negative mindset and have that, you know, oh, here we go again. I don't know what I'm doing on the phones. I'm, you know, it's gonna be the same thing as last week. It is, it's gonna be the same thing as last week. But if you come in and you say, all right, last week wasn't good, but it's over. It's time to restart, do something new. You're gonna see the results and you're gonna ultimately, you're gonna get better. And you're going to improve. And I think also that comes from like seeking help and again, asking questions, talking with your coaches, the resources you have, and expressing that you're struggling and expressing that, you know, I need to get better.

17:37 Scott Ingram: Let's talk about April. So April for, I think, a lot of people in sales was, you know, one of the hardest months they've maybe ever faced in their careers. I mean, everything sort of shut down and it was, oh my gosh, what, what do we do? And not only did you figure out what to do and get back to even, but you set a record in that environment. How did you do that?

18:00 Kyle Hermann: Yeah. April was a really solid month. And I think where my success in April stems honestly came from the end of March. And what happened at the end of March was that was about when everything kind of shut down. I remember like it was yesterday. I mean, I flew home because our office had gotten shut down. So I was going to be working remote for the extended future. And when that happened was actually the same day the NBA got shut down. And then I think soon after that, the MLB canceled all their stuff and all the sports got canceled and the world was kind of… no one knew what was going on. And there wasn't much talk about anything reopening. Businesses were at that point going to have to figure out what to do. So it was a sensitive time for a lot of people. And in that week where that happened, it was probably the worst week I had as an SDR. I got hung up on, people were calling me insensitive for making cold calls. People were saying like, I might not have a job soon. Like it was an uncomfortable time. It was a tough time, a lot of rejection. But what comes with rejection is trying to figure out how to get better and how to fight through the current climate and how to learn to sell in that environment. And one thing that I came into was, and it was talking with my dad and a few other close family and friends, is with it being such a sensitive time, you have to show some level of humanity and being empathetical with your approach. So that started for me with going into my calls and asking how their day was. How are you holding up? How are you doing today? And then also thanking them for taking my calls. So being really appreciative for their time because I think time is pretty sensitive. People are in back-to-back meetings and with the climate the world was in, I think it was extremely important to show that you really took appreciation into what they were doing for you. And then from there, just having a conversation, being a salesperson-to-salesperson kind of approach and understanding and being there for them in a tough time. I think that's what separated me from the rest as far as being able to generate so many opportunities and really building meaningful and strong relationships with my prospects at the time.

20:30 Scott Ingram: So it sounds like that probably goes back to the questions and the curiosity, right? It was just getting in and Like, how are you guys dealing with this? What's going on? That kind of stuff, right?

20:39 Kyle Hermann: Yeah, yeah, exactly. Yeah, that combined with just… and I think it, after a couple weeks when people were starting to be at home and talking to the same people every day, they were looking for something different. They wanted that conversation. So when people are coming in and just trying to pitch, pitch, pitch, that's not going to go anywhere. At some point you need to take a step back and maybe crack a joke, have a conversation and be a human. And Yeah, I think that's what stood out and really put me apart from the rest. And, you know, you got to be able to break through the noise in a time like, like COVID, where people are still getting hit up all the time. And it is just not a great climate to sell in.

21:17 Scott Ingram: So yeah, but you know, it's interesting, though, I think at the same time, it's just the fact that you pushed through and persisted. I mean, what I found through that period was, I was able to easily get ahold of so many more executives so much more easily than I would normally, because normally their calendar is just wall-to-wall meetings. There's, there's not a lot of time that they're even necessarily at their desk and able to pick up a phone. But here they are like, okay, well, all those standing meetings more or less went away. And here we are sitting at home and I'm lonely and I needed to talk to somebody other than my, my wife and kids or whatever else is going on. I mean, it was, it kind of felt like there was a window of opportunity if you knew how to treat it. And you knew how to kind of respect the situation that it was. But the last thing you could do is… what wasn't going to help is if you stop. Like, if you don't call anybody, you're not going to get any meetings. That's, that's just the way it's going to work.

22:15 Kyle Hermann: Yeah, exactly. You said it best there. And you seem to notice the same thing when it came to people were picking up, I was getting more connects. So at that point, it was just finding out how to convert those connects into meetings, because the opportunities were there. You just needed to adjust accordingly.

22:30 Scott Ingram: Yeah, brilliant, brilliant, brilliant. Yeah. And unfortunately, here we are just a few months later. And that's all, that's all changed. We're all back to very, very busy, lots of meetings. And I would imagine your connect rates have gotten pretty close to where they were before.

22:44 Kyle Hermann: Yeah, exactly.

22:45 Scott Ingram: So let's ride the roller coaster here a little bit. And we'll start with kind of the high. What are you most proud of? I mean, you've had a pretty good solid run there at Outreach. Like, what's the pinnacle been so far?

22:56 Kyle Hermann: Yeah, there's been some pretty cool things since I've been around at Outreach. And I think for me, the biggest accomplishment that I've had is, you know, the numbers are great and everything, but at the end of the day, the thing I'm most proud of was this thing that we do every month, and it's called the Big Ups Award is what we call it. And this isn't an award that's just given to like an SDR or like the sales team, but it's actually an award given to every month by our leadership for the entire company. And I think it was back in December, I actually won the Big Ups Award. This isn't about performance. This isn't about, you know, what you're doing well. This is showing that you exemplify Outreach's core values. And that was, you know, there was a time where I had a, you know, a positive interaction with one of my fellow SDRs and, you know, a manager had seen that interaction take place and submitted it to, you know, our leadership team and got chosen for ultimately having my fellow SDR's back. So, you know, I think out of all the awards and numbers and putting up big numbers, that's the one that stands out the most to me. And I'm definitely the most proud of that.

24:03 Scott Ingram: That's awesome. And I love that cultural piece of we've got your back and the way that you guys demonstrated that, you know, not just with each other, but to the broader sales community and helping people, you know, find places that were still hiring and all that kind of stuff. It's really such a, such a cool thing. So what about the other end? Like, what do you struggle with the most? Like, what's the bottom?

24:22 Kyle Hermann: Could you explain a little bit further?

24:23 Scott Ingram: Well, just biggest challenge, the thing that, that you find, maybe this is something you've already resolved. Maybe there was a place where you're like, oh, I was just, I got stuck and I wasn't able to break through. Or maybe this is just something that kind of persists. You're like, man, there's still this thing that haunts me. And I feel like if I could figure that out, I'd be even better.

24:42 Kyle Hermann: Yeah. I think my biggest challenge right now, and it's also one of my, one of my biggest passions, to be honest, is breaking in and having conversation in markets that, you know, aren't as early adopters to really go out and invest in technology tools. I mean, we're pretty prominent already in the, you know, computer software, cybersecurity, high-tech-based companies. But there's other industries that are, you know, a little bit further behind as far as, you know, bringing on different tools. And my passion is going after those people. In my eyes, I think there's a use for sales engagement in any industry. And it's just a matter of where it fits in and how you spin it and how you use it. So it's a challenge though, at the same time, because you're reaching out to these old school folks who have done things the same way for 25, 30 years. And to tell them, hey, you should look into this tool that a 23-year-old out of college is trying to tell you to take a meeting. You know, it's not everyone's going to be so receptive to that. So I think that'd be my biggest challenge. And I still, you know, see it on a day-to-day. You still have those issues when you're trying to teach an old dog new tricks. But, you know, it's being able to find where you can add value and where you fit in. And if the prospect sees it, then they're going to be that much more likely to endure and take a meeting with you.

26:12 Scott Ingram: Yeah. All right. Let's go a little bit deeper into that in terms of how you're typically breaking through that, because I think a lot of us see that, right? It's not as hard to sell to an early adopter or somebody that's really progressive and likes to be on the, on the bleeding edge or front edge of things versus somebody that, to your point, is kind of a legacy type of industry. Maybe they don't grow the way that most of us in the technology space are accustomed to. And it's just a totally different type of sell. How are you typically finding a way through that?

26:40 Kyle Hermann: Yeah, I think you just, you gotta find where the need is and where the pain is. And where that comes in is doing a lot of digging on the front end, reading into 10-Ks, looking into workflows, how their teams are structured, who's leading those teams, finding out who the right people to reach, what they care about, what they're passionate about, and then accumulating all that information and using that and finding where what you're selling fits into that need. So I think that's kind of what I like to do when I'm breaking into these new industries that have never heard of Outreach or never have thought about investing into a sales engagement tool. I'm really just trying to find out where the use could be and then showing them and talking it through them and explaining way more high level and what the results it can help provide.

27:34 Scott Ingram: Yep. Love it. Love it. So let's talk about routines here a little bit. And the way I like to start to dissect this is walk me through your typical day, starting with the alarm clock goes off. Tell me what time that happens. And I want a pretty detailed blow-by-blow until your head hits a pillow.

27:53 Kyle Hermann: Love it. Love it. So am I talking pre-COVID or post-COVID?

27:57 Scott Ingram: Well, let's… that's a great question. Let's talk current reality. That's the world we all live in now.

28:04 Kyle Hermann: Yeah, that's a great question. And the reason I asked that is I actually try to do the same thing every day, whether it's I'm in the office or working from home. I find that a routine and doing the same thing, it keeps me focused. It keeps me motivated. I'm not going to be your guy that's going to get out of bed in the clothes that I'm wearing and go start to work. So every morning, you know, I I have to shower, I have to dress nicely, show up to work as if I'm going to be in the office. For me, that's a mental thing. I feel more ready to rock, feel more confident with myself. And I think that is super important as I go about my day. But yeah, when I structure my day, I mean, the great thing about sales is each day is different. And I think that that's what keeps it fun. It keeps it upbeat and enjoyable is that you're not just clocking in and clocking out. But with that being said, you know, there are ways that I like to go about and structure my day. Personally, I'm not a big morning phone call guy. I'm gonna come in, I'm gonna knock out my emails, anything that, you know, I'll put some people into sequence. For people that don't know what sequencing is, essentially that's, you know, our series of touchpoints and writing out that first email and getting that sent out. And from there, I'll do that for about Couple hours between mid-morning and early afternoon, I'm usually making phone calls. And if I'm not making phone calls, I'm having internal meetings, internal discussions, whatever comes about that day, because there's always something different that happens. And then again, finish the day out with just more sequencing and more writing more emails and putting people in for the next day and making sure that my pipeline's full and I'm reaching out to the necessary people. And yeah, that's probably how I go about my day-to-day. Obviously with my new role of being more in that senior, senior level position and working with the rampers and people that are new into the role throughout the course of the day, I do have a lot of questions to answer, Zoom calls that I'm hopping on to just get the basics down and ensure that the rampers are feeling comfortable and answering all the questions that they may have.

30:03 Scott Ingram: Yeah. I'm glad you brought that up because I wanted to ask about this earlier on, which is what's kind of the percentage of breakdown between just your own individual contributor prospecting efforts compared to this kind of coaching role that you have with the onboarders?

30:16 Kyle Hermann: Yeah. Yeah. I would say right now it's, I'd say it's about 50/50. Obviously the focus has gotta be, you gotta hit your number no matter what. But I think being able to take on extra responsibilities, you have to show that you already are confident and you're, there's no doubt in your mind that you're gonna hit your number. So for me, I got to that point where, you know, I knew what I needed to do to crush my results. And really kill it. So adding on the new responsibilities, that's where it got difficult. It got tough because for the start, the priorities had to be elsewhere. The priorities needed to focus on the new hires, the people who needed the support to get caught up to speed. So for me to be able to go about that and balancing these new responsibilities, I needed to be super structured, putting time on blocks on my calendar, basically going back to the basics of This part of my day, I'm going to be doing prospecting. This part of my day, I'm going to be working with new hires. So for me, I would say that that breakdown though would look close to that 50/50 mark. Wow.

31:17 Scott Ingram: So you found a way to be as productive as you were as your only job was to set meetings and then layer on this extra stuff and essentially half the time. Am I kind of getting that?

31:27 Kyle Hermann: Yeah. Yeah, you are. I mean, but the beauty of being an SDR and being more on the tenured side as well is By that time you kind of get an understanding and you know your workflow, you know what you need to do to hit your number. So for me, it's just filling in the gaps. And now it's come down to, you know, I don't take as much time in my day to mess around or do, you know, non-work activities almost. So, you know, I'm trying to focus in, hone in, right? Stay true to my calendar. And, you know, really like still, still allot the time that I need as an SDR to crush my number and then spend that leftover, you know, rest of that time working with the new hires.

32:12 Scott Ingram: Nice. I love that. And if you're anything like me, I'm sure it's just because I resemble this a lot. It just forces you to focus, right? It kind of forces out the fluff that you had in your day that really doesn't need to be there. And when you're in this situation where you've got to deliver on both sides, you just don't have time for it and it automatically kind of goes away.

32:31 Kyle Hermann: Mm-hmm. Absolutely.

32:32 Scott Ingram: So let's get just a little bit more granular. I'd like to understand more details like on, on the morning routine side of things, like what, what are the steps? Is there anything special you're doing? What time does your day start? And then let's just talk about the prospecting blocks. So in a, you know, 50% of your day you're focused on prospecting in order to get to, you know, 200% of your number What are those blocks ideally?

32:57 Kyle Hermann: Yeah, so those blocks are typically, you know, on my calendar where… and this is, you know, circling back to one of the tips and tricks that one of my old managers, Dylan Fletcher, what he kind of ingrained into me to… at the time it was to work on my KPIs and get those numbers up, but now it's even more of a use for, for other things. So I'm seeing the value in putting on blocks like, hey, from this, from 11:00 AM to 2:00 PM, I'm going to be calling and I stay true to that and I call for those 3 hours or from 7:00 AM to 10:00 AM, I'm going to be sequencing and I stay true to that. So I think a lot of folks get, they'll do that. They'll put those blocks on their calendar, but they won't stay true to it. Their mind wanders, something comes up and all of a sudden they got to go tend to that. So I think it's being able to focus in, hone in on what's on your calendar and hitting it hard for however long you have it on there for.

33:54 Scott Ingram: Yeah. So is, I mean, is that kind of the recipe? Is that the ideal that it's roughly an hour of sequencing and then a 3-hour call block? Is that the right setup?

34:02 Kyle Hermann: Yeah. So for me, I'd say I go about 2 hours in the morning to sequence. I would say I do, yeah, about like 2 to 3 hours a day of calling and then finish the day up with about another hour and a half. 2 hours of sequencing at the end of the day. So to structure that into my schedule and then leave that leftover room and fit that in for the other needs and the other responsibilities that I have as well.

34:23 Scott Ingram: Yeah. Now, is there anything special that you're doing in those call blocks just to make sure that you don't get distracted and you don't see like, oh, I got this email, I gotta, you know, something dinged on my phone, I'm outta here.

34:35 Kyle Hermann: Yeah. I think the best part is competing with other people and doing these call blocks, doing these blitzes with, with the team. And that's one of the things I love about Outreach is it's tough to do it now because we're not in the office and you're not feeding off the energy of everybody else on the floor. But what's great about it is, you know, we still do it as a team. We still have competitions, we run spiffs. So when we're calling in these blocks, you know, no one wants to lose. You gotta do whatever you gotta do to win. So having that healthy competition, I think that keeps everybody on track when it comes to staying true to your calls because everyone wants to make more calls and book more meetings to ultimately win different prizes, opportunities, lunches, whatever is decided on beforehand.

35:19 Scott Ingram: Nice. Now, are there any other habits or routines that are really key to the way that you operate?

35:25 Kyle Hermann: Yeah, it's funny you asked that. So one of my favorite routines is I need my coffee before I get in the call blitz. And I think it's funny how that works because I could definitely make calls and be just fine without it. But for me, I love, I'm a big energy guy. So if I get a couple cups of coffee or a cup of coffee in me, I'm feeling good. I'm feeling ready to talk to people, have conversations. I'm that A-type personality where I'm going to come in with the energy, come in with the positivity. And I think that really rubs off on the other side of the phone when talking with prospects. People pick up on that and are more inclined to engage with you if you're, you know, showing that sort of energy that, you know, the positivity and what you're bringing to the table. So that's where on my end, you know, I love throwing down a couple cups of coffee before I go about it.

36:14 Scott Ingram: Right on. Right on. So what about your information diet? You know, we've talked about the coaching and training being one of your kind of key factors. What are you reading, listening to, watching, and when does all that happen?

36:26 Kyle Hermann: Yeah. So I mean, I have actually pretty recently picked up on a new podcast that I've been diving into. It's called How I Built This. I don't know if you're familiar with it at all.

36:36 Scott Ingram: Guy Raz.

36:37 Kyle Hermann: Yep, exactly. But essentially I was actually referred to this podcast by one of our account executive managers and she ranted about it and said, this is awesome. And I think this one really fits well with me as well because I come from an entrepreneurial background and for some context, How I Built This was It's this podcast, which is great for companies explaining how they started and how they built their businesses from the ground up. And my dad, he started his own business. He runs his own business right now. In college, I studied entrepreneurship. I created my own company in college. And so this entrepreneurial background that I have, it really interests me into this podcast. And I really, really enjoy listening to see how companies come about and make it at the end of the day.

37:22 Scott Ingram: Nice. What was the business in college?

37:24 Kyle Hermann: Yeah, it was actually a gelato company. So Funny enough, it's actually a really cool program that's run through our school. I went to the University of Washington and through the business school they have an entrepreneurship program. And the great thing about that is they actually give you the opportunity to create, come up with an idea, facilitate it, and run your own business. And it's a 2-quarter class. The first quarter you come in, figure out what your idea is, learn, pick the brains of other people who have We get guest lecturers come in and you can ask them a bunch of questions about how they built their businesses. And then at the end of that quarter, you're then pitching your idea to actual investors who then give you money or invest in your product. And from there, you're using that to facilitate, drive sales, and build the product and sell it. And we did Gelato and super successful. We made profit on it. But at the end of the day, it was just a great learning experience and finding out how businesses operate and what it takes for these companies and people to be successful in whatever their interests may be.

38:30 Scott Ingram: Yeah. How important do you think that understanding of business and kind of that entrepreneurial business education, the ongoing curiosity and how I built this and all of that, how important is that to just your day-to-day motion and conversations in sales role.

38:47 Kyle Hermann: Yeah, no, it's super aligned. And I think I was joking about it with one of my friends the other day. When I was in the class, you don't really understand it because you don't see it on a day-to-day, but it's so relatable when you go into the workforce. And my goal, what I'm trying to do now is understanding how businesses operate, understanding where the pains are and where we can add value. And I think I've said that a few times now. And I think actually being in that position where you're trying to get a company off the ground and knowing what you need to do to be successful and drive profit, drive revenue, it was extremely informational. And I don't regret a single part of it, even though at the time there were some times where I was like, oh God, we got to make some more gelato here on a Wednesday night. But at the end of the day, I learned a boatload from it.

39:40 Scott Ingram: Yeah, awesome. So we got to one podcast. What else are you reading and listening to?

39:45 Kyle Hermann: Yeah, so there's another thing that was actually started here with a few of the members here at Outreach. It's called SDRs Anonymous, and I've been looking into that recently. And essentially it's SDRs have the ability to, you know, ask questions, anonymous questions to our page. And I don't run it, but a few of my colleagues do. And essentially from there they get SDR leaders or top SDRs or different people to hop on, you know, a huddle almost and be able to answer those questions for the audience. And I think that's super helpful. Again, like, it aligns super well with my idea of don't be afraid to ask questions, right? So being able to see this firsthand and seeing it take off, you know, I'm loving every second of it.

40:28 Scott Ingram: Yeah, great stuff. And as always, we'll have a link to that and everything else we talk about at top1.fm/96 or top1.fm/Kyle-Hermann. And my regular listeners are totally laughing at me right now because I actually know what number the podcast episode is going to be. So let's see, let's talk about the tools and apps and just kind of your personal tech stack, which I have to imagine starts with Outreach. But what else kind of makes up the core tools that you're using on a day-to-day basis?

40:58 Kyle Hermann: Yeah, I mean, as you said it best, everything starts with Outreach. Wouldn't live without it, wouldn't work anywhere that didn't use Outreach. So Obviously I'm a little biased here, but that's my firm opinion. But yeah, I mean, I live out of Outreach and then some other tools that I use, love LinkedIn Sales Navigator and that combined with ZoomInfo, fantastic tool for just finding contacts and generating and being able to source leads. I think it's unbelievable. I know they just IPO'd pretty recently this past week and they're absolutely killing it right now. So it's cool to see that. And so love those. And then just like any way to get a foot up, like using tools like Crunchbase and understanding if a company has received any funding, company news. I love those. I love resources like that where it's just adding any sort of extra personalization, any way to make a conversation warmer. And that's the end of the day, that's the goal. So I would say those 3 are the ones that would stand out to me the most combined with outreach as well.

42:03 Scott Ingram: So yeah, it's interesting. You keep coming back to this idea of the personalization and the humanity and those kind of components. I'm curious about maybe it was that, maybe it was something else, but it sounded like as you were talking through your coaches in the early part of your journey that maybe you had sort of an inflection point or you're like, Oh, I get it. I mean, it almost sounded like something clicked. Is that fair? Like what happened?

42:29 Kyle Hermann: Yeah, it really did. And I owe that all to, again, I'll, I'll say his name again, is Dylan Fletcher, 100%. That when I was on his team, that's when it clicked. That's when I became the best SDR that I could be. And what he did a really good job of in relation to this idea and this piece of personalization is so many SDRs will come in with some sort of personalization and They'll say something that's relevant and whatever, and you're just trying to catch attention. But what I think what separates a good SDR from a great SDR is being able to tie in that personalization with value and where you fit in. Where, for me, where does outreach fit into their current business or the current person's responsibilities, their needs, and being able to find that out. In explaining that in a phone call, explaining that in email. And for me, that's when it clicked. And that's when I was seeing results. I was booking more meetings, phone meetings, email meetings, LinkedIn meetings, whatever it was, you know, things just started working and falling into place. And I was able to see the direct results from it.

43:38 Scott Ingram: So give a specific example of that.

43:40 Kyle Hermann: Yeah. So I think my idea when I'm looking into and researching into an account, we We run an account research document. So it's basically finding anything about the company or about the prospect that we can find. So looking into 10-Ks, looking into previous opportunities, previous conversations that we may have had, and looking into specific prospects. What are they responsible for? Tying it back to what their workflow is. Is it, do they have SDRs? Do they have AEs? Are they full cycle? Are they field? Are they, you know, what are their reps responsible for doing? How are they doing that? Are they outbound prospecting? Are they inbound? Is it primarily an inbound shop? And this is all stuff you can do on the front end and by just doing your day-to-day research. And I think that's pivotal. And then tying that into when I'm actually writing out an email, the way I like to structure my emails, and I do the same thing with my phone calls, is coming in with that personalization. Hey, you know, I noticed or saw you're responsible for XYZ, or I saw that one of your big company initiatives from your 10-K is XYZ. And then I'll provide the value of what Outreach specifically does. And then I'll finally tie it back to how we can specifically help their current need.

45:03 Scott Ingram: Nice. Nice. So, A, I think you've convinced me. This has come up a couple of times and now I'm gonna have to find a way to fit it in. I'm actively working on building the agenda and the lineup for the Sales Success Summit in October. And one of the things that's come up is just a session on how to read a 10-K as a sales professional. I think it's a, it's a skill that not enough people really have. And there's a little bit of, well, it's not so much art to it. It's just, you know, having a good process for doing it. How did you learn that?

45:31 Kyle Hermann: It's a good question. And to be honest, I could still be better at it. I haven't fully mastered how to work through a 10-K. But the previous senior SDR, her name was Carrie Olson. She trained us on how to read through it. She would do it pretty heavily when she was an SDR as well. And she just taught us, you know, different keywords to search for. So whenever I'm going through a 10-K, I'm looking for words like sales, like revenue, like technology or sales tools or tools, and just kind of spot searching and see what comes up. And, you know, people might listen to me here and say, God, this guy's an idiot, but Maybe there's some other way. So I'm always looking for new ways to, you know, improve my research game and really dive into it and see what works best. So I wouldn't say I mastered it.

46:17 Scott Ingram: You set me up perfectly for my follow-up question, which is how do you find that right balance between research and activity? Right. Cause it's, it's so easy to just go off the research deep end and then never make a call ever again.

46:30 Kyle Hermann: Yeah. I think, I think research is pivotal, but like, I agree. At the end of the day, you gotta pick up the phone, you gotta make your calls. But especially in the enterprise space, you can't just get away with spray and pray. You can't just blindly call someone and hope they pick up and talk about outreach without any relevant stuff. I think people realize that it's just like, these guys are getting prospected. These people are getting prospected every single day, 30 times. I'll get on phone calls and you're like, this is the 30th time someone's called me today. Like, what do you do differently? So like if you just come in with no personalization, it's going to be a legless call or a legless email. Like I think that's where personalization comes in key. And once you do that on the backend, from there it's just, it's plug and play. You come in and you use that personalization. It's in your notes. I mean, Outreach, thankfully we have that following us every part of the screen that we go to, but it's there and you can just see it and use that within how you're crafting up emails and how you're talking to people on the phones.

47:33 Scott Ingram: Yeah. Do you ever set any sort of time limit to say, okay, I'm going to spend 5 minutes on this account and then I'm done, I'm going to get as much as I can, or any way that you sort of manage the time that you're spending in research?

47:44 Kyle Hermann: So I wouldn't say I have like a time limit on it. There's usually like a certain amount of prospects that I'm looking to put into sequence. And the way I like to tackle my accounts is I'll kind of just do one at a time, one account at a time. So really dive in, I'll pop open, you know, pop up an account, do all my account research, my digging on them. And then from there, find my prospects, plug and play. And I think, I mean, if I were to put a timeline on it, it would probably be, you know, 30 minutes to an hour a day researching and sequencing an account.

48:17 Scott Ingram: Got it. So it's almost an ABM-centric approach. Like, this is my account for the day, I'm going to deep dive on that account, I'm going to find all the contacts, I'm going to do all of my first email drafts, and then the next day you might be on to another account.

48:30 Kyle Hermann: Exactly, exactly. And that's what I, you know, when I, when I say like I separate time throughout my day, like I have the morning where I'm sequencing and the afternoon I'm sequencing, that's combined with the account research as well.

48:41 Scott Ingram: Yep.

48:42 Kyle Hermann: Got it.

48:42 Scott Ingram: Got it. Now, Kyle, how would you describe your style?

48:45 Kyle Hermann: Yeah. Yeah. So I would say for my style is I love to try new things and try out new strategies. So You know, if I hear something I like, if I see another rep doing something that I'm like, wow, this is pretty cool, I'm going to try it. I'm going to do it. And if it works for me, I'm going to keep it. And if it doesn't, oh well, I gave it a shot. So I think that's something I really pride myself on is I don't like to hold back. And, you know, if someone else is seeing success, I'm going to take that. I'm going to implement it and do what I can for it to be successful for me as well. And I think that's the beautiful part about sales development is you feed off your peers constantly.

49:19 Scott Ingram: Yeah. Where are you looking to find that? I mean, maybe it's helpful being in sort of this coaching role that you're in, right? That you're listening to a lot of other people. Does it come from that? Are you seeking out other high-performing reps? Like, where are you finding those sources of inspiration to inform what you're trying?

49:35 Kyle Hermann: Yeah, I think you said it best right there. Like, being able to listen to calls constantly and doing just that. I think one thing that tenured folks get complacent with is they figure out their process and they, they stick to that and they don't really look to improve it or try new things out. Oftentimes new SDRs come in all the time and bring something new to the table and have new strategies. So I'm always looking to learn things from newer SDRs who are brand new to outreach. Maybe they came from a different company and they did something different and it worked well for them. Well, fantastic. I'm going to see what they did differently and see if there's a use and figure out a way that I could, I could do it here at Outreach for myself. So like I said, I think circling that back, I just think that being able to collaborate with your peers and collaborating with other top performers, you're going to feed off of each other and pick up new strategies and ideas to keep you growing as an SDR in general.

50:35 Scott Ingram: Yeah. It's kind of the big secret of mentoring. You know, I find a lot of times when I'm helping you know, younger professionals who are earlier in their careers, I get just as much value, maybe more value than they do, right? Like, sure, I've got a lot of experience, but you've got fresh ideas. And you're just seeing this totally differently from the first time. And a lot of times, it's just that, that shift in perspective in that new way that breaks through all the… this is what everybody's doing right now. So it just doesn't work anymore.

51:04 Kyle Hermann: Exactly, exactly.

51:05 Scott Ingram: So I always like to ask, is there something you believe that the average SDR would think is crazy?

51:12 Kyle Hermann: Yeah, to best answer your question there, I think a lot of SDRs would say I take on a lot of responsibility. And this stems from, you know, whether it's the senior role and doing a lot of, you know, work with new hires and training and onboarding and coaching, or I've also spent time on the events team at Outreach. So going in, I mean, back in the day when events were a thing, going into different conferences, trade shows, in doing that. I was also part of the sports, our sports go-to-market team. So, you know, one of the big industries that we were looking to break into were, you know, sports accounts, ticket sales. And I think, you know, I really enjoyed that. I'm a sports guy through and through. I grew up, you know, watching, playing, loving sports. So being a part of that was pretty cool. But, you know, with that came a lot of extra responsibilities. And I think this also stems back to what I was talking about with time blocks and really structuring my day. Because at the end of the day, there was less time in my day for messing around and not participating in whatever sequencing or coaching or whatever that entailed. And people think I'm crazy because I block off my calendar, but I feel like I'm in grade school or something like that where it's class to class. But I think that's helpful for me to get through my day and stay true to what I need to be doing and making sure that I'm doing whatever it takes to get my necessary work done within the course of a day. So I do recommend it as well to my fellow SDRs, as this was also passed down to me by my old manager. So I think it's a fantastic strategy.

52:49 Scott Ingram: Yeah. What about the flip side? Is there something that typical SDR believes that you think is crazy?

52:55 Kyle Hermann: For me, It's objection handling. It drives me crazy because I think your average everyday SDR, they don't like objection. It's uncomfortable. But I think objection drives conversation. I think if someone is objecting, they're interested. You've caught their, you've caught their attention at something. So now it's just being able to handle it and then ask a question in return, spark conversation. Right. That's at the end of the day, that's what you're trying to do. Get insight, gain intel. So, you know, I think one of the things that, you know, when SDRs, when they face objection and they, you know, they don't have any further questions to ask and they hang up the phone themselves, you know, I think that's a little crazy and I try to keep talking until the person either books a meeting with me or hangs up on me.

53:49 Scott Ingram: And so, I think what I heard, it's so funny because minutes ago, you know, just before we started this conversation, Mike Simmons sent me a couple of pieces of audio for some Daily Sales Tips. And one of his was around objection handling. And he's like, you know, look, it's just ask a question. Like, you need to understand exactly what they're objecting to. And it sounds like that's very much your approach. Like, that's awesome. This is just an opportunity to go deeper into the conversation and really get at what, like, what's, what's going on here.

54:19 Kyle Hermann: Exactly. And don't get me wrong, I, you know, I love it when someone just says, you know, you come in with your, your introduction, they're like, yeah, I'll take a meeting. Like, those, those are the best calls you get. But I think where you learn and grow as an SDR is, is learning how to handle objections and ask the necessary and proper questions to follow up and understand where the pain is and how you can help solve that.

54:41 Scott Ingram: Yeah, great stuff. So what have been the most important decisions you've made or lessons you had to learn to get where you are today?

54:49 Kyle Hermann: Yeah, one thing I think my dad used to always, always tell me is, is hard work beats talent when talent doesn't work hard. So essentially, you can be the most fluid, the smoothest, the best person on the phone or best SDR, know exactly what to say. But if you don't work work hard and you don't put the time in, the results aren't going to come. You may hit your number, but you're not going to exceed it. So putting in the hours, putting in the work, putting in the time when others aren't, that's when it gets noticed. And that's when I think for me, you know, that's what's gotten me to where I am today. Nice.

55:27 Scott Ingram: Let's go back to something you and I talked about just a little bit before we hit the record button. And that was kind of where are you setting the bar? Like when you think about goals, when you think about expectations for yourself, What is that?

55:39 Kyle Hermann: Yeah, I think for me, it's, it's, I don't like to stop. You know, I, some, some, some reps that, you know, they hit their number and that's the rest of the month. And, and for me, I feel uneasy if I don't keep going and push my pedal, you know, push my foot down, pedal to the metal until the end of the month. And I think just this, again, it stems from competition. It stems from sports growing up as a kid. Like you never want to, you never want to lose. I hate losing more than I enjoy winning. And if I don't put my foot down, I'm not going to be at the top every month, in and out. So I think that's important. And also being able to find people, find other top performers on the floor to compete with, to push you. And there's one of the SDRs on my team, his name is Brennan Vaughn, and we go back and forth all the time. And we feed off of each other, we trade ideas from each other. But at the same time, every month, we're competing, who's going to be the top. And it motivates us to be the best and really keeps us on our game and put the foot down until the end of the month.

56:45 Scott Ingram: Okay, so talk more about that. Because I love that, like, how have you developed such a, like, productive sense of competition, right? Because I think there's 2 types of competitions. There's, there's the competition you just described. And there's the competition that would have you discover some strategy that is just massively helping you improve and you wouldn't share that with him.

57:11 Kyle Hermann: Yeah.

57:11 Scott Ingram: Like, oh, this is my trade secret. I'm not going to do that. I'm going to use that as my leverage to beat you. But it sounds like your relationship would be, nope, I'm going to give you that tool too. And now let's see what we're able to do.

57:21 Kyle Hermann: Yeah, I think it's at the end of the day, you got to understand that everyone's here for the same reason. Right? For the greater good of the company. We're trying to source meetings and source pipeline opportunities so our AEs and our closers can close more business and generate more revenue. That's the goal. So I've never even… it's never crossed my mind that I wouldn't want one of my SDRs to not do well, to miss quota or perform poorly because we're all in it for the same reason. We're all trying to get better. So I think feeding each other ideas and we started the same month, we've been competing back and forth since we started. And he's one of my closest friends in the office. And I obviously want him to do well every day, but I want to beat him every day. And yeah, I think just understanding that we're in it for the same reasons and we're here to support the overall growth of Outreach. And that's what we enjoy doing.

58:16 Scott Ingram: Yeah. And I think a lot of it is also the underlying culture. Right? It comes from what's going on in the office. Because again, I've seen it the other way probably more times than I've seen it in the way that you described, right? Where it's, it's really, I'm just trying to beat you. And we're not thinking about the bigger, like, how do we all help each other win? Because we all, you know, we're in this together.

58:38 Kyle Hermann: Exactly.

58:38 Scott Ingram: Even though we have individual numbers.

58:40 Kyle Hermann: Exactly. You said it best there.

58:42 Scott Ingram: So let's, let's talk to the folks that are just starting out? I get a lot of folks reaching out to me who are thinking about getting into sales or, you know, they're, or they're looking to get into software sales. And so they're thinking about the SDR role as a good entry point into the industry. What advice do you have for somebody that's just starting out in their sales career today?

59:04 Kyle Hermann: Yeah. Yeah. I mean, it's crazy because I also feel like I'm just starting out here in my sales career as well. I mean, I've only been at Outreach for a year. I graduated college a year ago. So, but in sales years, it feels like it's been forever. I feel like I've been part of the organization and I feel at home. So what I would say to people who are starting out is, and this is exactly what Alec had told me, my mentor when I first started, and he was a top performer, and it's A, pick apart whoever's best. Whoever's at the top, do what they're doing. And then at the same time, get good on the phones, put in the extra work earlier, set yourself up for success. When you're meeting with people, a lot of people get in the habit of putting time on every person's calendar, which I'm not a big fan of doing because you're just going to hear conflicting ideas and you're going to confuse yourself. So find the top performers, know what they're doing, and model your day-to-day around theirs.

1:00:12 Scott Ingram: How can folks who are new to an organization… and let's, let's forget about the process that you have where you've got the onboarding and you're already kind of mapped to them. But let's imagine that I come into your organization. I'm a brand new SDR. I see you. I see that you're the top performer. I want to implement your idea. I want to go learn from Kyle. How should I treat you? How do I ask for your help? Right. How do you want to be approached and what's the best way for me to manage that relationship?

1:00:43 Kyle Hermann: Yeah, I think for me, it's treat me as an equal, treat me like I'm one of you. I mean, I am, I'm an SDR as well. I'm full quota carrying SDR. And, you know, I respond on email, I respond on Slack, I respond in person, whatever, whatever the form of communication is, you know, I just, I think it's important for newer reps to, they get shy, they get complacent. They don't, they feel uncomfortable asking for your time, but I'm always down to meet with someone if they need the help or want the help or want to put in that extra work to be successful.

1:01:14 Scott Ingram: Yeah. Is there a wrong way?

1:01:16 Kyle Hermann: That's a good question. For me, I would say my big thing is if you're going to ask for time, come in with an agenda, come in with stuff that you want to talk about and want to work on. Don't just come in to talk to talk. So I think that's something that newer SDRs don't get in the habit of doing is they'll just expect me to tell them everything that I did to be successful. But it's hard to steer a conversation or steer what their problems are and knowing what they want to work on without them coming in with something and telling you what they want to work on. So then you can best be in the position to help them. Yeah.

1:01:54 Scott Ingram: Yeah. And part of my point in asking that was, for whatever reason, I see this a lot. There's so much intimidation around asking for this kind of help. And I think the reality is, man, we're all happy to pay it forward. Like there's people that helped us get to where we are, and you're just hurting yourself by not going up and asking the question and asking for the help. And I think your advice around, you know, being specific about it, you know, having some purpose in what you're asking for and not being just general and saying, so Kyle, how do I do it?

1:02:27 Kyle Hermann: You know, it's exactly…

1:02:28 Scott Ingram: you got to get a little bit more focused than that. I wonder, is, is there anything that we haven't talked about yet that is kind of a core part of what you would want to share though, right? If you were sort of building the curriculum of how to extract all the success secrets and tips out of Kyle's brain, is there any ground that we haven't covered in this conversation that really should be part of that curriculum?

1:02:49 Kyle Hermann: Yeah, yeah, absolutely. And I think One of the most underrated ways to prospect and be a successful SDR is also building a relationship with your counterparts, that being your account executives, right? You're interacting with these people every day, you're booking meetings for them, get to know them. Whenever I would introduce myself to an account executive for the first time, whatever it was, I would get to know them. What do you enjoy doing? What are your hobbies? So we could be like-minded, find something that we're both passionate about. And me, I'm a relationship builder. I love meeting new people, making friends, and that's my end goal. So I wouldn't say I have a poor relationship with a single account executive that I work for. And at the end of the day, if you are a solid SDR with a good relationship with your account executive, you're going to be more inclined to work well with them and book more meetings for them and push yourself to help them out in turn as well. So I think AE-SDR relationships for companies that have that business model, it's, you know, something that we, we pride ourselves on at Outreach and it's pivotal in my everyday and how I interact with, with my colleagues.

1:04:04 Scott Ingram: Nice. Now, does that also help you in your prospecting motion and in terms of the way that you might be coordinating around accounts or things like that?

1:04:12 Kyle Hermann: Absolutely. 100%. Yeah. And one of the things that I love doing with my account executives is tandem prospecting and kind of getting a feel of, you know, maybe I start out and send out an email and my account executive comes up on top of me and, you know, the combination, the dual prospecting skills sparks the prospect's attention and they're more inclined to take a meeting with us. Or if my account executive says, hey, you know, Kyle, you talk to these people, I'm going to talk to these people. And we'll meet in the middle and see what we can find and come up with a systematic plan of attack to each account that we work.

1:04:47 Scott Ingram: Yep. Yep. Great stuff. Is anything else in that curriculum, any other ground that we didn't cover that's like, Scott, we have to talk about this?

1:04:53 Kyle Hermann: Yeah. And I think the last thing that is coming to mind is building your brand and building an internal brand within the people you… and this also aligns with working with your account executives, but more so on a broader scale, like just working with everybody in the office, coming in presentable, dressing nice in the office and coming each day with a purpose to get better, getting to know other departments, other people within your company, being a pro when it comes to coordinating and working with C-level, VP-level executives. And really just having them know who you are and what you're about and that you care and we're all in it for the same end goal and to better the organization.

1:05:43 Scott Ingram: Yep. Glad I asked. So what about, I mean, I've interviewed bunches and bunches of people and asked lots of these different questions. What would you want to know about the top sellers or the top SDRs in other organizations outside of Outreach?

1:05:58 Kyle Hermann: Yeah, I'm always hungry and always curious to hear new ideas and For me right now, what's top of mind is making that transition from an SDR to an account executive and maybe other SDRs who are in that same position with me where we've worked our way up, we're at the senior levels, enterprise level SDRs, and the next step could potentially be an account executive role. And I'm always curious to hear what other people are doing to further their resume and further their skillset to be best prepared for when the time comes and they have the opportunity to interview for that position, what they're doing to be successful?

1:06:38 Scott Ingram: Yeah, great question. I mean, we've probably covered most of it, but what else are you doing? And maybe those 2 go together, right? It's sort of preparing for that transition, but also the brand that you're building. So when the opportunity to interview comes up, you're a known entity, right? Like, hey, this is somebody who's, who's consistent. Like we, we know what Kyle stands for. What, what else are you doing along those lines?

1:06:59 Kyle Hermann: Yeah, I would say for me right now, what I'm trying to really get a grasp on is it's a lot different to talk about outreach in a 4-minute call versus a 30-minute, an hour-long initial meeting demonstration. And I think a lot of SDRs get in this mindset where it's like, it doesn't really go much past the initial meeting. That's all they really care about. Where when you get to an account executive role, you know, there's a process that's involved. And I know at Outreach, we're talking to a few of our sales leaders, we're big process-oriented. You gotta be able to run an initial meeting, a demonstration, a proposal, you know, it goes down the list. And being able to like hone in on what that is, studying up on the different plays and situations that we run with our potential customers, combining that with meeting up with account executive mentors, people that have been in the role, maybe people that transitioned from an SDR to an account executive role at Outreach, pick their brains. Also talked with account executive management because they're working with their reps on a day-to-day. What are they seeing that has been successful with SDRs becoming AEs? And then ideally, hopefully one of the things I would appreciate doing here soon is potentially even learning to take smaller meetings, smaller deals, and having the opportunity to work those and getting some practice in before that time comes.

1:08:23 Scott Ingram: That is awesome. You know, I had a conversation earlier today, and I don't think I'm speaking out of school because I think this is all good stuff. I'm going to say very positive things about, about all of them. But I was talking with Katie Ivy, who's the RVP of sales at Demandbase. And I recently interviewed… I guess it was, it was late last year, I interviewed the top SDR at Demandbase, and that was Vin Matano. And Vin's now on Katie's team and he's in an AE role. And she's like, man, he is just doing so great. And we were talking about, she's like, you know, they're another one of these companies that does a great job of managing that SDR pipeline and moving them into AE roles. And she's like, you know, it's not uncommon for us. And these folks usually do well. I think the trap that a lot of companies have is there's no ramp from one role to the other and they're very different roles. Right. So, you know, just because you were a great SDR and then let's flip the switch and now you're going to be an AE, it's just a different thing, right? There's a lot of skills that absolutely transfer, but you've got to be kind of prepared for it. I asked why I was like, what is so special about this? And I think part of it was the length of time that he spent in that SDR role, because he got really, really great at it and took the time to really develop himself and learn to understand the AE role. And then she was also talking about, it was just having the broader mindset of the totality of the territory and understanding like, this is essentially a business you're going to manage, right? So keeping your head wrapped around that is just, there's again, too few organizations that are creating this type of progression, but those that do it well are reaping massive rewards and having just Not only incredible SDRs, but incredible AEs as a as a result. So I'm I'm sure that you're on a similar path. I know I know Outreach has done again a lot of those types of transitions. I've seen a lot of people move up within that organization. You guys are growing so quickly; it can happen very fast for you if you're doing the right things, right?

1:10:25 Kyle Hermann: Exactly. Yeah. I mean, Outreach does a phenomenal job of you know if you're doing well and and if you're building your brand and hitting your number, of course, and not just hitting and exceeding your number, solidifying yourself as a top performer, things will work out and they're going to find a place for you to level up and get to the next level. And I'm seeing it firsthand with one of the guys who just got promoted a few months back and just to see how much his skillset has changed and learning, just really leveling up and learning so much more and what goes into a deal outside of prospecting and seeing his progression. I see that and I'm like, wow, I want that for me as well. So it's motivating to see it and know that hopefully at some point it'll come my way as well. Yeah.

1:11:19 Scott Ingram: That's just great, great stuff. And I've got a couple of resources for you and I'll share them with everybody else that's that's listening. And it sounds like you've kind of done this work because when we were talking earlier, you know, I was asking you about, you know, what's next? Where do you want to, where do you want to go from here? And you, you know, have kind of done the soul searching and thought about, you know, I really want to be an individual contributor. Last year, really the last 2 years, the last 2 Sales Success Summits, we've had a lot of panels around just being intentional about that, that type of career management and thinking about where you want to go and how you position for that and how you think about that. And I started usually the way that this is supposed to work. So depending on when you're listening to this, if this is too far into the, into the future, this, I may have gone back to the original, but pre-COVID, the deal was when you join the listener list at top1.fm, I will let you pick any video that you want from, from any of the summits. And I'm happy to send you a promo code to get access to that. And in these, I like to call them challenging times, different times. I'm just giving everybody access to all the videos. Just, you know, it's, it's our way to make sure that we've got everybody's back and are helping support the sales community through whatever they're working through. So, you know, it doesn't really cost me anything to put the videos out there. So again, if you join the listener list at top1.fm, you'll get links to the video sites and you can kind of see what's on there. And I'll either give you access to all of them or you can pick one, which one's relevant. But there are a few sessions on there that are very keyed into this idea of what is the right path and how do you make those decisions and hearing from people who have been in a variety of different roles who've been in leadership and they've been individual contributors and why they chose the paths that they chose. I think it's just good to make informed decisions around that stuff. Let me ask this too, because I've enjoyed asking this here frequently in terms of what you think, and maybe it's premature, but what do you think is the right amount of time to spend as an SDR before, like, you've really got it down? And you're probably ready to start thinking about that transition to an AE role.

1:13:25 Kyle Hermann: Yeah, that's a great question. And I think one thing that our sales development leaders built out and now he's actually our director of SMB sales. So he's overseeing the entire SMB sector of account executives. And he actually was the enterprise SDR manager prior before I was on the team and right around the time that I started. So he and our VP of sales development, They came up with an idea of 6 months fully ramped in an upper segment. So for us, that's a corporate, so mid-market to enterprise level in 6 months of hitting your quota in a row, being fully ramped. So I think that's a very adequate amount of time because you can master your skillset on the emerging level, master, you get even better and level up way more Coming into upper segments as well and learning how to talk with VP-level, C-level executives on a day-to-day. From there, I think 6 months is a beautiful amount of time just to bake out, really understand what you're doing, how you're able to be successful, to drive enough value, find a pain, ask the right questions. And honestly, I still feel like I'm learning something every day, which is awesome. Because I think if I learned everything already, I'd be burned out and it would be boring for me. But being able to still be hungry, still learn something new, it keeps me on my feet. And so the short answer to your question would be, I would say about 6 months in a fully ramped segment.

1:15:01 Scott Ingram: Yeah. So that ends up being kind of a 2-part piece though, right? Because that sort of assumes that there is just the fundamental learning in a lower segment. So what does that end up being in totality? Like how much time do you need to spend learning the fundamentals? Before it's appropriate to move up into the, into an upper segment?

1:15:17 Kyle Hermann: Yeah. So we typically see it as like a year in total. I know I spent 4 months on the emerging team. So again, that's just really baking yourself out as an SDR, being comfortable with prospecting, being comfortable with making cold calls, learning how to talk with these people, learning how to properly personalize emails and know what people are looking for and what they care about. Like learning those different skills are a necessity. And I think that would take for about, you know, 3, 4 months for someone to learn.

1:15:50 Scott Ingram: Yeah, perfect.

1:15:51 Kyle Hermann: Cool.

1:15:51 Scott Ingram: So let's wrap things up here. I will remind everyone, if you've been loving this and you want more of these, remember top1.fm/sdr is the shortcut to all of the previous SDR episodes. Kyle, if you were to boil this down, into an action that our listener could take to improve themselves and improve their results over the course of the next week or 2, what would you have them do?

1:16:17 Kyle Hermann: Yeah, I think what I would boil this down to is get comfortable with the uncomfortable. I think that's where, where growth happens. So, you know, a good challenge would be anytime you feel nervous or scared or, you know, feel sort of uncomfortable, take that first step, pick up the phone, ask the question, just force yourself to do it and put yourself out there. And at some point, that uncomfortable is going to start being comfortable for you.

1:16:43 Scott Ingram: Beautiful, Kyle. This has been a blast. Thank you so much for joining me today. Really enjoyed our conversation, and I know I will be seeing you here in Austin in October.

1:16:53 Kyle Hermann: Fantastic! Looking forward to meeting you in person, and I appreciate the time here, Scott. Thanks for listening to the Sales Success Stories podcast. To be sure you never miss an episode and. And for an invitation to our Sales Success Community, powered by Influitive, subscribe to our newsletter at top1.fm.