John Smallmtn (00:01.41)

Welcome to another show of The Adapted Growth Show, everybody. I know, a truly original title. Today we have Tanner Cookson on the show. Tanner is the Director of Sales at Alternative Payments. We met really recently while I was speaking at an event, and we were hanging out talking about sales nerd stuff and leadership. He had really interesting things to say, and I’m super excited he’s on the show. Welcome to the show, man. I’m so glad that you’re here.

Tanner Cookson (00:26.506)

Yeah, thanks, John. It was awesome meeting you the other week. Honestly, I’m super happy to be here. I think it’s so fun. Sales to me is one of the most compelling careers in the world. Just the conversation we had about teams, building culture, confidence, and all these elements that make up great sales processes—to me, that’s what this life and my career is all about. So, thanks for having me.

John Smallmtn (00:52.594)

Absolutely. I think we’re going to have a lot of very interesting tangents to explore in the conversation. One place that I really want to start—because this show is really about adapting in different situations so we can get the growth and do what we need to do—you came into the role that you’re currently in as the sales leader, is my understanding. You were in leadership in the old sales role. Is that true?

Tanner Cookson (01:13.77)

Yep. At my last company, I managed the SDR division there. We had a big-sized team spread out all across the US and Canada. Then I came into this role from a player-coach type perspective. I was responsible for everything: picking up the phone, doing cold calls, closing deals, and having some leadership elements. I was really just one of those players that tried to do it all.

John Smallmtn (01:45.782)

There’s going to be so much to talk about with the player-coach thing because everyone has very strong opinions about that, myself included. Going back a little bit to the last role, leading that team of SDRs, can you talk about some of the challenges and maybe changes of perspective that you had to go through moving into that leadership role? Because there’s the hard component of the numbers and the results, but there’s also the soft side component of culture, enabling, and motivating. Where did you struggle stepping into that leadership and management role in the old company, if anywhere?

Tanner Cookson (02:25.022)

Yeah, I mean, I think there is so much to learn and so much to comprehend. I probably spent every waking hour of my day just trying to figure it all out and trying to understand how to wrap my head around how we position the team. When I moved into leadership in that last company, it was a crazy time for the business. Within a month or two of moving into that director role, we had acquired two or three other companies. So, we brought this SDR team that was six or seven people at the time, and then it immediately doubled overnight.

We had all these different remote teams and all this consolidation of bringing in companies that were all their own individual startups, bringing them under one SDR organization, and trying to figure out what the hell our identity was. What does that look like? Who are we? I think that was the hardest thing for me to figure out. Each SDR team kind of had its own approach to how they book meetings, how they run their cadences, what their sales style is, and what their expectations are.

So, I think the hardest thing was spending a lot of time with each individual and then as a team trying to understand: What is your goal? What’s your expectation? What do you believe in? What’s the culture you want to see? How do we merge all of that together to take four or five great cultures and combine that into one? That’s where I had the most difficult, but also the most rewarding, time just figuring out what to really do and where to go with that.

John Smallmtn (04:19.542)

Man, I personally feel like that’s a really cool moment in time, right? Because I’ll work with teams where people on the same team aren’t using the same process, the same labels, or the same titles for any of this stuff. But in this situation, it actually makes sense that they were doing it very differently because it was a wholly different organization. Did you lose anyone during the transition? Were they unable to put down the ego or the old habits, get on the same page, and do it the same way that the rest of the team was? Did you lose anybody during that transition, I guess, is the better, more succinct question?

Tanner Cookson (05:04.37)

Yeah, I think we lost people before anybody gave it a shot. I think that happens with a lot of acquisitions and mergers that happen within companies. A lot of people find it a scary event, right? Change is super scary for individuals, especially if you’re coming from a startup organization and moving into something bigger. It’s really scary to think about how that job might change, how expectations might change, or what compensation, quota, process, or team might look like six months down the road.

I think what happens to a lot of people is they get more afraid of the change and they step out before ever giving themselves a chance. We found that we had a couple of people step out before that process change ever even happened. Once that process change happened, we really retained pretty much everybody from the organization. Everybody that stayed ended up staying not just for a year, but multiple years after, and a lot of people were then able to accelerate into different career paths and opportunities within the organization.

I think a lot of flourishing happened. But again, during that early-stage part when that change just happens, people freak out. Teaching and coaching on how you manage that change internally and use that as an accelerator rather than a detractor from a career perspective is key.

John Smallmtn (06:40.702)

Holy crap, I love that. Looking at the question differently, how much did you pull away from what they were doing as far as their cadences, their outbound, and their motions? Did you pull anything from them and integrate that into what you guys were doing? And if you did—sorry, two-part question—was that intentional to try to build team cohesiveness, or was it just outperforming and you said, “We’re going to steal this, use this, and borrow this for the sake of the team”? Or was it like, “What do you guys do really well? Let’s try to do that.” How did you get to that place of meshing all these different cultures?

Tanner Cookson (07:26.162)

How I really look at teams in general in sales is micro-awareness, not micromanagement. One of the things I always tried to be extremely diligent and focused on was that whenever we were working with any team and building this out—and this goes for the exact same thing today; I think I’ve taken this through all of my jobs and tried to keep this mentality—it’s not about taking somebody, plugging them into a single process, and then telling them exactly what to do, which is micromanagement. Doing $X$ number of calls, $X$ number of emails, $X$ number of activity, and doing it in this cadence—those metrics help people get off the ground and running.

But when you’re bringing in experienced teams, it’s more so about teaching them how each individual can get to a point where they understand their own KPIs. They’re coming to me and saying, “Hey, this number of calls equals this many demos for me. This many emails equals this many demos for me.” Then what we tried to do is take all of those different ideas. We had some teams that were literally using an Excel sheet and a cell phone, just picking up and dialing away. We had other teams that were using HubSpot cadences that were super advanced and tied into marketing. We had other teams that were using different platforms like Salesloft and had a whole different set of cadences—maybe email-heavy and call-light.

We just tried to first map it out to the buyer journey. What are the buyer expectations? How do we accelerate? Each product sells into a little bit of a different audience, so how do we make sure we’re matching up there, taking best practices from all of these different organizations, and then trying them across different teams? We spent a lot of time testing. There’s a ton of things I learned. The one thing I consistently harp on for any new person that joins my team or when I talk about sales is: I don’t know what the best technique for next month is. I know what worked last week, maybe last month, but I don’t know what works this week or next month. We always have to be pushing and trying new ideas because it’s only from testing that we’re going to get better results.

John Smallmtn (10:01.446)

Interesting. The tech nerd in me wants to dive into that because I imagine some people are on a spreadsheet calling on cell phones and other people are HubSpot-driven. Meshing all of that and getting everyone on the same page is a unique puzzle because everyone has their ways.

I’m also a big fan of not giving everyone the same kind of KPI goal as far as “you must do 100 activities.” It removes any drive to be better at the job, in my personal opinion. You just think, “I’ve got to do these 100 dials,” and then when you get put on a write-up because you’re not having enough conversations, we’ve almost missed the boat.

I’m a big fan of a midpoint KPI being the first one, like meeting count, discovery count, or demo count—something in the middle of the process. That way, there’s room for individual reps to figure out what volume they need to do to hit that metric. That’s uniquely difficult because it creates a lot of empowerment in individuals and room to mess up, but I also think they carry the goal better as opposed to being what my coach called an “at-leaster.” You’re not doing super well, but at least you’re hitting the metrics. I love that.

With all these different acquisitions, if I’m hearing you correctly, they were not all in the same market or to the same kind of audience. It might have been selling different things to different people. Is that true, or was it about making a better product for one market?

Tanner Cookson (11:48.858)

It was the same market, but for different people within that market, like for IT or different divisions within that market. Your buyer was actually different people within the organization, so it was very different people.

John Smallmtn (12:02.05)

Very different people, it sounds like. That’s interesting. Do you have any other tips for people who might be a sales leader inside of a company that’s doing lots of acquisitions? Any other tidbits of knowledge that might help someone else out if they’re a sales lead in a very growth-oriented, buy-by-acquisition type of business?

Tanner Cookson (12:28.914)

It’s a hard thing to wrap my head around, and I still made a thousand mistakes and had a tough time. I think the biggest thing is that change is a great thing; it’s the perception of change. Most people just perceive change as being scary and feel unsure about their job.

One of my biggest mentors tells me all the time, “Live like ‘fuck it.'” You have nothing to lose in this career. Everything is icing on the cake. You have to live with that mentality—not saying you don’t care and nothing matters, but the opposite. Don’t be afraid to make decisions, to make choices, to be assertive, and to purposefully drive things in the right direction because you’re scared of what could come in the change.

Instead, go into that organization and do the best you can with the best intentions, and good things are going to happen. Especially if you involve the people around you and think of this as a team effort, whether it’s the SDR that just started two days ago or the person that’s been there for 10 years and now just got acquired under your umbrella. Every single person is valuable. Just bring them all in. Don’t try to do it all yourself. Do it as a team and go with the mindset of, “Let’s just try to figure this thing out, build something unique together, and make us all owners in this process.”

If you can go in with that, there’s not a world where you can’t be successful. You’re going to make mistakes—everybody is—but you’re going to be able to work around them because you’ve got the whole team behind your back.

John Smallmtn (14:41.854)

Okay, so I was going to change gears, but you brought up something there that I have a couple of questions about. SDR is a grind: very activity-driven, very activity-heavy. It’s also an entry-level sales role, so a lot of times we’re bringing in people who are brand new to this role and have never been in sales before. There’s lots of reluctance and avoidance. Do you have any tricks or tips that you’ve uncovered about helping new SDRs get accustomed to that grindy cadence of doing more activity than they think they need to in order to backfill with intention? Any tips about getting people started or having that mindset shift that they’re going to need to do more than they think?

Tanner Cookson (15:30.578)

I love this topic so much. I’m so glad you asked about this. I think there’s this massive difference between motivation and drive. The way I think about this is like people who train for a marathon or do sports—there are a lot of sports analogies here—nobody wants to wake up at six in the morning and do a run because they’ve got a marathon coming up in a couple of months or next year. But they know they have to to be able to get to that spot.

John Smallmtn (16:08.312)

Yeah.

Tanner Cookson (16:13.41)

And it’s the people that are driven, right? Whether it’s raining, whether it’s cold out, whether they woke up tired, anything like that—it’s the people that are driven that are always going to find that success. I think what a lot of sales mindset gets to, and a lot of what sales teams get to, is that short-fuse motivation. It’s like, “Hey, hit this activity metric,” or “Let’s do this spiff for the most amount of calls or the most amount of $X$ in a single day or a week.”

That yields very short-term results. It’s not sustainable, it’s not really teaching the rep anything, and it’s also just teaching them, “I only need to do this when I get rewarded for it.” But that’s not actually true at all. You need to do that every day of the week.

So, what I think about is: First of all, how do we hire for driven people who fundamentally are those A-players? Whether they have experience or not doesn’t matter. Do they show up every day in life looking to wake up and do what needs to be done?

The second part of that is enforcing that, talking about that, and being open about that within each of those conversations—just asking, “How do we get there?” It’s not a motivation thing. It’s really about coaching around that repetition of: Put in the work, and the results will follow. You kind of have to disassociate the results from the work at first, focusing just on the work and worrying about the results one or two months down the road.

John Smallmtn (18:05.054)

Oh man, it’s so interesting to me because I remember being a rep, and leadership would come in offering a gift card for some carrot that I didn’t care about at all. I always hated it. But I also know that I’m not the standard personality type for sales roles. Part of that constant skepticism that I have keeps me from buying into some of those situations.

That is very interesting to me. So, question then: Do you think that siloing the sales approach—having BDRs, SDRs, and AEs over here who close business versus full cycle, just to put it into those two very distinct categories—do you think we’re improving sales as a role, as a function, and as a craft by doing the siloed approach? Or do you think that being full cycle is ultimately better for salespeople and organizations?

Tanner Cookson (19:08.99)

I mean, it’s a tough question. I’ve been in organizations that do both. My last company was very siloed. You’d have your SDRs who were just responsible for the pipeline generation side, and they were all partnered with AEs who were fully focused on closing and didn’t book any pipeline.

At my company now, our team is very lean, nimble, and agile—we’re a startup. Totally different dynamics, right? You don’t have that consistent flow or the budget that you used to have. Now we’re in a position where all of us do everything. I’m about to jump on a cold call block here in 45 minutes, and I’m going to be picking up the phone with all my reps. We’re all responsible for everything.

In terms of what is better for who, that’s a question the organization has to answer. Ultimately, the way I feel about it is that if you’re in a position where you have an incredible product-market fit, you’re highly successful in outbound, and you have a really good marketing flow, then it absolutely makes sense to have a sales team just closing deals. If you can fill that pipeline, then hell yeah, have at it. Get really good at closing those opportunities and just run through those all day.

But again, if you’re in more of that startup environment, you’re still kind of figuring out where to go, and you need to create that opportunity—to go out there, be boots on the ground, make those dials, and have those conversations—we’ve all got to play our role and play our part. At the end of the day, almost all of the most successful AEs I’ve seen—whether they’re directly responsible for it or not—all pick up the phone, make those dials, and generate that pipeline. So, it doesn’t really give a simple answer to your question, but that’s kind of how I think about it.

John Smallmtn (21:11.258)

Yeah, it drives me crazy, this idea that people are moving into sales… I had a conversation recently with a guy who’s never been in sales before, but wants to be in sales and wants to come in as an AE. He asked, “Can I pick your brain?” I was like, “Absolutely, happy to help anyone who wants to move into sales. Let’s have a conversation.”

I told that guy, “Look, if you don’t spend any time prospecting, your people are going to know it, and they’re not going to be able to trust you when you try to give them help. If you have someone who’s supposed to be setting appointments for you and building pipeline for you, and they’re not doing a good job, there is no passing the buck if it’s done well.”

If you’re an AE who has an SDR setting for you and they’re not doing a good job, you’re supposed to be in there backfilling that situation and showing them by example what it takes to fill that pipeline—as opposed to saying, “They’re not doing a good job, but it’s not my fault.”

I think that’s becoming harder and harder to do because it is so siloed. Some of these people who have been AEs for three, four, or five years have prospecting skills that are out of practice and a little rusty. So it’s one of those things: Do we take a really good closer and make them prospect too? It’s a very hard, interesting challenge to work with. I was just curious as to your take on it.

Now, before we hit record, we talked about an idea that you called the “invisible finish line,” which I think is such a unique name. The way that you talked about it to me was that you just knew the work was done, and you knew it was time to go find something else. Honestly, that’s a big reason why I work independently for myself: When it’s time for me to go, it’s time for me to go. Once I’ve figured out the puzzle and it’s no longer a challenge, I start to get dismissive and a little bored with the situation. I don’t really hear most other people talk about that unless they’ve made the decision to go out on their own.

Can you talk a little bit about what that finish line felt like for you? How did you know that it was time to move? Was the writing on the wall, or did you just wake up and decide?

Tanner Cookson (23:42.422)

Yeah, I mean, listen: All of us have invisible finish lines all throughout our careers. Every single job we enter has what I believe is that goal of what we’re all trying to get to. The hard part is that you never know when you’re finished and when you’re not finished.

For me at my last company—look, I started there as an SDR. This goes back to your last point: I was an AE at the job before that, and then I went back to being an SDR to relearn some of that skill and work my way back up. It’s the greatest spot in the organization to learn and to become successful. So, I did that, worked my way up, and eventually became the Senior Director for the BDR division.

I had been in that job for two and a half years. We had acquired probably six or seven companies at that point, and we had taken the business from $10$ million in ARR to $75$ million in ARR—massive growth. We built this phenomenal team. Then I went to the office one day on a Monday, and we did our team call. I sat on that one-hour call—our Monday stand-up across the whole organization—and I didn’t have to run it. I sat there and realized, “I didn’t have to run it.”

I had this phenomenal team of SDR managers that I got to raise up through the organization. The team was really mature. We had incredible talent across the team that had been there for a really long time—they were tenured and experienced. We were hitting all of our metrics; it was really good. I just remember coming off that call and being like, “Wow, I think that’s my sign.”

It’s a difficult thing to do. I remember talking to my fiance—my wife now—and I was just like, “You know what? I think I’ve really accomplished my goal.” I felt so good about that. It was at that time where I was like, “Okay, I think it’s time to start this all over again and put myself back in the fire.”

Careers go to die when it’s comfortable. The moment you feel comfort is ultimately the moment to either go to your boss and say, “Hey, I need more,” or it’s the moment to say, “Hey, it’s time for the next thing.” I just remember really feeling that and thinking, “Okay, I feel really good about what we’ve got here.”

John Smallmtn (26:45.891)

Yeah, I tell lots of people that I’ve had way too much coaching because I’m like you now: If I feel something, I try to figure out why, and I want to be aware of it. It’s interesting because some people ask, “John, how long are we going to work together?” It’s like: For as short a time period as possible, because I’m trying to give you what you need, and then I’m going to go find something else.

I also think that lots of other people take the opposite approach: “Cool, I’ve done the heavy lifting, and now I just get to manage.” On both sides of that conversation, I have moments where I worry about complacency. On some level that bothers me, but on another level, it’s a job, it’s a living, you’ve done the big part, and now there’s some consistency. There is something beautiful about having a consistent lane as a salesperson, because there is so much other chaos that we have to figure out how to thrive in. At least having the knowledge that the role, the team, and the product-market fit are set—that’s one less thing to deal with.

How long did you sit with that feeling of, “Okay, I feel like I’ve done a good job here, and I think it’s time to go do something else”?

Tanner Cookson (28:01.646)

Three months. Three months, yeah. I remember sitting there starting off the year in January, and I think I ended up leaving in April. Again, I had to reaffirm it. I asked myself, “Am I jumping the gun too early? This is so comfortable, so why wouldn’t I stay?” The company had an exit strategy, and there were things going on that gave every reason to just hang out and take it easy.

But I made this promise to myself years ago: I never want to be comfortable in a position. Reward doesn’t come from not taking risks in life, and I think there’s a fun element to it. To be fair, not everybody can afford that risk in their life. I feel very gracious and grateful to be in that position because my wife and I rent an apartment in Toronto, we don’t have kids, we have a dog, and we’re young. We were in that position where it was okay to step out because nobody else was counting on us—we didn’t have kids counting on us.

I feel grateful to be able to take that risk, but it is something that really means a lot to me: Always push yourself. I think it’s the same thing with hobbies outside of work, too. Push yourself to always be a little bit uncomfortable, and I think great things will come from that at some point.

John Smallmtn (30:05.238)

Man, I love that. I appreciate you talking about the fact that lots of people are willing to do the slog of a startup because there is an outsized exit opportunity. Was it hard to walk away from that idea? Because there are some people who feel, “Cool, I’ve earned this. No harm, no foul.” If you’ve figured out a way to get to market and have repeatability and consistency in the sales motion, you’re doing a good job and you’re due part of the exit if you’ve been around that long. Did you have any concerns or struggles about walking away from potentially bigger exits and bigger money if you had stayed?

Tanner Cookson (30:52.194)

A little bit, but honestly, not really. The way I feel about it is: Life is too short to wait on things.

John Smallmtn (31:02.006)

Love that.