E10: Mark Bergen on Aligning Sales Product Partners and Mission

That's nice, but thanks, but no, we don't want to do it. And I was just flabbergasted by the whole thing. And I found out that actually the executive were maintaining a list of large brands we'd said no to. And it was a point of pride. It was huge. So every other organization I'd worked with had a huge list of all the clients we'd won and all the big logos, and that was the point of pride. This was the opposite. It was actually, here's all the large logos we've said no to because we're not going to deviate from being a product-led organization. And if they're not ready for us and we're not ready for them, that's totally cool. and we were really proud about that.

Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com, and every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes. But first, a word from our sponsors. This episode is brought to you by Momentum.io. Momentum is a powerful tool for turning sales and customer conversations into go-to-market data. Using GenAI, it extracts, analyzes, and automates customer intelligence across your org. The best part? It's not a new platform for your team to adopt. It integrates seamlessly with your existing stack and writes data back to Salesforce directly. Some of the most innovative companies out there, like Zscaler, Demandbase, Ramp, 1Password, and even my company, owner.com, use Momentum every single day to capture, forecast, and churn risk, autofill Salesforce fields, share product signals, and track sentiment. So check it out with a free trial at momentum.io. Mark Bergen, welcome to the podcast. Super excited to have you here, my man.

Thank you, Mr. Norton. Good to see you.

Good to see you as well. So I'm going to do a separate intro before, but give folks your 60-second bio so they know who you are.

Sure. So, Mark Bergen, I'm a Canadian. I've been in sales for about 30 years, either in kind of sales leadership, revenue leadership. Kind of fell ass backwards into it. I was a science guy, math guy out of university and got married young, needed work and ended up in a sales role basically because I talked too much in a young company that was struggling to try to find product market fit. And so, I ended up in a sales role and that really took my career off. I spent the first 8 or 10 years because I hadn't planned on sales and really have a vision of it. I spent the first 8 to 10 years trying to get out of it. So, I did a bunch of education around it, thinking about finance, thinking about other things I wanted to do. And, I was in my young 30s, ended up at a company called Vision Critical, which in the Canadian market space, kind of a 2005 vintage company, took off really quickly. And that was the first place I worked for a leader in Jason Smith that really impressed me. He was a good human. He exemplified what good looked like, cared about people, cared about doing really good work. And so it's the first time I actually saw a path of, oh, revenue leadership can actually be a really wholesome place to hang my hat and there can be really good work done here. And so that took off. So I spent 10 years at Vision Critical. We took a pretty quick sprint to $100 million and stalled out there. Left in 2015, took some time off, then Shopify called. And didn't know e-commerce, didn't really know Shopify. At the time was about a $250 million business. Was really interested in learning kind of a high-speed inbound sales motion. Most of my career to that point had been kind of that broad, big, you know, outbound enterprise stuff. So I took a risk with them and yeah, took off. So spent 6 and a half years there, which was a pretty wild ride. Left in late '22 and at the moment find myself doing a whack of fractional work, which at the moment is really enjoyable.

Nice.

Awesome.

How big was the sales team at Trop when you started?

We were, so for context, I suppose might help the rest of the conversation. Shopify Plus, we built it out to the side of the organization. So Shopify, very focused on the entrepreneur, very PLG in its motion. I was brought in to basically start building out a sales motion for Shopify Plus, which was for the enterprise where you had successful businesses with an established technology, established platform. So it was a rip and replace, considered purchase, a lot of risk.

So to answer your question, different definition of enterprise.

Yeah, totally. Enterprise is a very loose term. We're talking merchants that are doing like $1 million in online sales and north of that, which for an entrepreneur running a $1 million business, that's pretty successful and pretty good. And so ripping out the guts of that thing and saying, hey, you should plug in a new piece of technology that frankly hasn't been seen in this size business before and is known broadly in the market as being for enterprises or sorry, for entrepreneurs, that was a fairly risky proposition for them. So we built it kind of separate office out in Waterloo. The rest of the business was headquartered in Ottawa and Toronto. So when I joined, to get to your question specifically, Plus was around 70 people total and the sales organization was about 15 of which at least half of them had been hired in probably the previous 8 weeks before I joined the business.

Awesome.

Yeah, pretty wild to think about.

And yet it was a $250 million revenue business. And so like a well-established self-serve model with the core product. And so the topic we're going to spend some time on is how to succeed in a product-first organization, in an engineering-first company, how to best partner with product, And then we're also going to spend some time talking about, uh, partnerships. Partnerships were a huge driver for Shopify success, uh, certainly the Plus organization in a big way. And, and so you've got some really interesting thoughts which, which we'll dig into. The other part of your bio that, uh, we didn't get to that's arguably the, the most impressive and important accomplishment is you gave me my start in tech. Uh, I cold-called you out of nowhere having not much on my resume other than hawking crappy conferences. And I'm forever grateful for that chance and tagged along to Shopify with you at some later point. So we've actually— so we've known each other for, gosh, was that 8, 8, at least 10 years old?

That was probably even later than that, 2012, something like that. So yeah, it's been 10 or 12 years. Yeah, it was probably the best call I ever took cold. Glad you and I went for coffee.

Yeah, always appreciative. I wanted to make sure that one was on record. So you're doing fractional now. I'm curious, one more leading question. What's the biggest lesson you've learned from doing fractional work now for a year plus that you would want to take back operating?

Yeah, I didn't get into Fractional with the serious intention of this is where I want to take my career. I knew coming out of Shopify, I'd done two relatively fast-paced businesses and my career is generally punctuated by fairly long periods of time. Vision Critical is a 10-year run, Shopify was 6.5 years. And so, when I came out of it, I knew I wanted time off and I wasn't sure what I wanted to do next, but it was obvious that the hopping back in, take a CRO role of a larger company, I know it, it's obvious. I understand the benefits, I understand the cost of doing it, but I wanted the chance to step back and actually try some different things. And you always have this list of like, oh man, if I had time, I'd love to do X, I'd love to do Y. And so I had a chance to kind of plug away at a bit of that. And in the midst of it, I had two companies separately got introduced by investors that called with different problem sets and said, hey, working with this company, both of them mid-size, $100, $100+ million businesses, both struggling with different problem sets. Would you come in and just have a look at the business? And I had time on my hands. I thought, sure, why not hop in for a month and have a look at the businesses? So in both cases, went in, did an assessment of kind of where they were at, the problem set, tried to understand the problem itself deeply, and came back with an assessment, said, yeah, here's what's going on. Here's where you're at. And as I see it, here's what I think you need to do. And in both cases, they came back and said, well, do you want to join us and implement this stuff? And for different reasons, I didn't feel I was the right CRO for either of the businesses. So my response to this was like, no, but why don't I lean into it if it's okay, a couple days a week, and I'll see if I can help guide the organization and the leadership there towards where I think we need to go. And both of them kind of said, yeah, and it's turned out really well. And so to answer your question specifically, Well, I haven't necessarily planned on it. One of the things I've really enjoyed about it is the contrast with my career, which has been getting very deep around a particular problem. This is the opportunity to see lots of different problems. And so, for example, one of the areas that I don't have a lot of experience in is building PLG motions. One of the companies, my conclusion recommendation was we need to build a PLG motion. It's a low ARPU product. They'd build a sales team. The economics don't work. We need to find a new way of doing it. That I think is PLG-based. And so it's been super fun kind of going deep on that and trying to understand like, what is it? What are best practices? And because I'm fractional, I don't actually own the number. I have way more time to actually study the problem, talk to other people in the industry that I think are experts at certain things. So there's been a lot of learning with it. So I think that would be one of the biggest ones that come out of it. I think the second is it has been an opportunity to think hard about problems and make sure I understand them really well before going deep on things. And I found as an operator, I'm an action-first guy. I tend to just get busy and do stuff and there's always things to do and breaking the time to actually step back and try to see the forest in the trees and ensure you're heading the right direction, actually understand the issues well. I've enjoyed doing that and hopefully I'm learning that as a deep lesson that I can take into an operating role if I choose to go there next.

So deeply resonate with that.

I'm surprised to hear you say that. You're one of the most thoughtful, well-read leaders I know out there. I'm surprised to hear you say that.

I think it's the nature of the beast. You're always pulled into action mode, especially in hyperscalers, right?

It's just nonstop. You're firefighting 24/7. There's always more, there's always growth, there's always an issue. And I've found in my career, one of the challenges has always been to step back out of it and try to see the problem fresh. And I failed at it in lots of areas. I can look back at my career and wish I had done things differently and realized I'd gotten too kind of heads down on the train I was stuck on. And this has been really nice to be the guy as the outsider, to be able sometimes to step back out of the leadership group and say, hang on a second here. Do we actually understand the problem? Do we have a good sense of why we're doing this? So, yeah, I've really enjoyed that, and it's been good education and good learning for me.

So, what will you do different? I need this advice for myself. If you were an operator today, what structure or framework would you put around yourself to give yourself space to think about the problem and not get sucked in?

It's really interesting you ask that because I've been thinking about that recently. I did have a company call that I've decided to at least have a couple of conversations with. And I actually started asking myself that question. What would I do differently in my day-to-day if I were to become an operator? How would I bring these lessons with me? And I tried, I've tried in my career to block out a couple hours here and a couple hours there to try to think. It never works. You're too caught up in the middle of the day with whatever's happening, Slack hits, there's a crisis, things intrude on it. And so, I don't know if I have a great answer for you. I think one of the things that I'm attempting to do is actually break significant time. It's not 2 hours in the calendar because it's never going to happen. But actually, 2 days or 3 days or try to get away. For me, often it's I need to get away from the computer or the laptop and take a notebook and try a totally different environment where I can just sit out free distraction, leave the phone at home, which is super crazy to do nowadays. But I need to really find a change like that. And so, I don't know, that's what I try. Take a notebook and a pen, get away from your laptop, get away from your phone, and try to take a full day somewhere.

Yeah. So, my head of RevOps who's worked with me for 8 years now across a few different companies, he did exactly this. He took his Remarkable, it's like an iPad, but it's like black and white, and sat in a hammock this weekend because his wife was out. And I was like, "Oh, that's a great idea." I don't know how I would find the time to do that with kids, but a new space. I think finding a new space, having more than just I do the same thing. I was like, oh, I got 3 hours of focused time. I'll do this, this, and this, and then slacks from the night before.

One tip I've been telling others, and I'm not sure if I'm good at doing it myself. One tip I've been telling others. So, I worked for Loren Padelford at Shopify for 5 years, and he's a phenomenal leader, learned a ton from the guy. And one of the things he used to do, and I only realized in retrospect, He'd leave on vacation, be like, I'm gone for a week, 2 weeks, I'm off. I'm not touching my phone. Don't bug me. By the way, can you take this? You're responsible for that. He would just download all of his key responsibilities and they cross the executive team. And of course, more exposure to executives, you're happy to take something on that's his domain, gives them more profile. So, yeah, sure, I'll take it on. And he'd come back and he would never ask for it back. And then you suddenly realize 4 months later, why the hell am I doing— I've already got all this other stuff and I'm doing parts of his job. And he did it explicitly. He would just hand it away. And when he came back, he would naturally realize either what wasn't working, what was on fire, I need to take it back. Where someone overloaded or needs help, I can potentially step in or take it back. Otherwise, he just continued to download his responsibilities to give himself the time to actually focus on what he should, which was work on the business, not in the business. So, I always reflect back on that and it took me unfortunately too long to realize what he was doing, but I thought it was brilliant.

That is a good one. I like that. Okay. Let's, we're going to transition into our first big topic, which is partnering with product and succeeding in a product-first company. And in Shopify is not just product-first, it's engineering-first. And I always joke with people about my time there. There's a clear hierarchy. It's engineering, then product, then design, and product management. Bunch of things, janitorial services, and then sales is like just right one under there. And like I say that jokingly and I actually loved that part of my Shopify experience. I learned so much from being in a product-first company because I had never really been. I don't know if you disagree about Vision Critical, but that seemed to be fairly go-to-market-centric. Yes. And so it was my first exposure to the deep craft of product management in a way that it was woven throughout the entire DNA of the company. And I did a Reforge course and I got into a bunch of product management podcasts and newsletters, and I felt like it was one of the biggest lessons I took away from my experience. But also, I don't think comfortable for everyone. And I think it takes a specific type of leader to be able to adjust to that. But there is a lot of unique value. And so just to cue it up, I'm curious, had you worked for a product-centric company before that, or was this a new—

Not at all. My career had been largely classic go-to-market function. Sales is our number one priority. We listen to customers. That's how we're going to drive our roadmap. And Shopify, to your point, not that in the least. Very product-oriented.

Maybe before I ask the question, do you want to give folks like a concrete example of how serious Shopify was about the customer and the product coming before revenue?

Um, we had, uh, it was actually interesting. We took So sales leader in an organization, it's pretty obvious what you're measured on, pretty obvious what you're there to do. And we take great pride in bringing great customers and great business into the organization and a lot of pride on driving revenue for the organization. And I had countless experiences in my first 3 or 4 years bringing really large organizations, and I'll leave names out of it, but big organizations to the table that would be game-changing. And organization would look and be like, nah, we're not interested because they all had custom needs. They needed some to be done. And the organization would look and just be like, nah, we're not that interested in doing that work. That's nice, but thanks, but no, we don't want to do it. And I was just flabbergasted by the whole thing. And I found out that actually the executive were maintaining a list of large brands we'd said no to. And it was a point of pride. It was huge. So every other organization I'd worked with had a huge list of all the clients we'd won and all the big logos. And that was the point of pride. This was the opposite. It was actually, here's all the large logos we've said no to because we're not going to deviate from being a product-led organization. And if they're not ready for us and we're not ready for them, that's totally cool. And we were really proud about that. That was a stunner to me. Didn't help me achieve my number.

No, I think that's a perfect example of what I'm getting at here. And it was because they wanted something that was not on our existing roadmap. And the existing roadmap was about building for most customers with most of their needs, and they weren't going to deviate to do anything custom just to win a fortune.

And even beyond custom, because I can understand in a company with a million or a couple million merchants, we're not going to do a custom one-off. But even something was like, well, this might hit 1% of the merchant base. Unless you could arguably look and say, somewhat demonstrably, this is actually a common problem or it's going to be a massive unlock for merchants and actually make commerce better. There was just not a lot of interest to it. So you could come in and be like, hey, I think we could add, I don't know, 50 merchants if we did something like this that would be big profile or pretty good GMV or pretty good revenue for the business. No, that didn't cut it.

Yeah. And that was, I think, unequivocally the right way to do things because the product roadmap continued to move at a fairly dizzying pace. And even just in the short time, the 3 years I was there, I saw the product go from quite competitive in enterprise to being like pretty de facto, you know, an obvious choice. It was sort of a matter of when, like when would a, you know, a larger enterprise customer say, okay, sure. The right time to replatform. Like, it, it, the, the gulf between Shopify's product in the enterprise and others was only widening.

So I think it was, it was really interesting. One of the things that, um, one of the other things that I found really interesting when I moved into the business was they just had a different sense of time. And where, particularly as a public company, and most public companies you talk to are operating on, you know, quarterly basis, maybe annual, but likely quarterly, right? We got to hit analysts' expectations. We got to meet the street. We're looking at our share price. Toby did not care and he had a long-term vision of what he was building and that was the direction we're going to go. And he had a very deep understanding of the merchant problem and he had a very deep sense of conviction of what he needed to do to actually make entrepreneurship better, have the best product in the market. And so, It very much led the business. And so even when it came down to getting numbers, I remember being stunned that it was, we had quarters where we'd miss a number, we were going to get really close, and the organization was okay with that. It wasn't hellfire coming down or you need to do what you can to stretch the target. It was like, that's okay. We're building long-term. Think long-term. Don't make short-term decisions. So give another example. I don't believe at any time in my 6 and a half years at Shopify, I had variable compensation. Which was the first time in my career as a sales or revenue leader, I did not have a significant portion of my compensation being variable. And their rationale for— we talked about it openly many times. The rationale was, if we put you on variable, you're going to think short-term about achieving short-term targets, and we don't want you to do that. We want you to create long-term greatness and something that's going to be sustained over the test of time. And so we are going to avoid putting that pitfall in that trap in front of you. I thought that was a fascinating way to look at it.

Yeah, I didn't have variable with my time there either, and it broke my brain when I first got the offer. And, you know, Ian had to walk me through the rationale and I got it. And then it was such a powerful lesson that now my current comp plan is 80/80 base, 20 variable. I said to owner, you know, hey, look, you don't want me on a 50/50 plan. I cannot resist my own urges to make money. Like, if you put half of my compensation up for grabs, like, I got kids and a house, and humans just in general can't resist optimizing for that outcome. And Shopify was such a powerful lesson that I was really, like, strong in that opinion. Not that I had to be. Our founder was really open and excited about that view. And this is one of the most common pieces of advice I give to founders now hiring their first heads of sales. Like, look, you're going to give them the wrong quota. You're going to have to reforecast consistently. Like, if you're a Series A company going from 2 to 10, like, you're going to be wrong almost all the time. And if your sales leader is tied to this weird number, they're making short-term decisions. You're putting, like, all this undue stress on them and you're going to get poor customer quality and weird culture stuff happening. And more than a few folks that I know that are heads of sales or CROs that I've given this advice to or founders are now taking this approach. Will Burch talks about this a lot. One of his recent Science of Scaling episodes, he talks about putting people on full base salary. Your first reps, none of them should have a variable. So I think it's catching on a little bit.

I think so. I think almost back to— I mentioned up front, one of the things I've really enjoyed in this fractional work is being able to really try to understand the problem well. And I think to your point, when it comes to compensation, when I talk to founders and think people who are calling about, hey, how do I set up my first comp program? How do I hire my sales rep, et cetera? One of the questions I always ask straight out is, what are you optimizing for? And understand that really, really carefully. Do you need your first customer? Do you need a dollar revenue? Are you building something long-term sustainable? Like, where are you in that path? How stable is your financing at the moment? What is the board asking you to do? Because the moment you introduce a compensation program, you very quickly create your culture for the business, and you've told people really clearly what you expect them to do, and they'll do everything to go and achieve that number. So I agree with you. I learned a ton about compensation, and I'm a big fan, especially for senior leadership. Of not having variable or having very limited variable as part of what they do.

My sales team had no variable comp when I got there. Then we introduced variable comp, then COVID hit and we pulled them off of variable comp. No discernible change in, in active behavior.

Yeah, that's my experience as well. Yeah. Find the intrinsic motivators for junior reps.

Like these are all first 3 to 5 year career individuals. I think that's less and less true as you move into mid-market and enterprise, but that was an interesting lesson learned for sure. So in terms of the big— the question I was going to ask was the biggest lessons in working for an engineering-centric org. And we've talked about a few of them. So thinking long-term, and one of Shopify's values is that they're trying to build a 100-year company. Variable comp. What else were your big lessons working for an engineering-centric company?

One of the things I really appreciated about Shopify was, and I think actually as I've sat back and thought about that experience versus previous experiences, and even now in the companies I'm in, I'm dealing with one which I would argue is more product-led and one that is definitely more commercial-led. And It's kind of back to that cynic golden circle, bullseye, or whatever he has, right? Where Shopify had a profound sense of why, and then sales had to figure out how to take the why and package it and figure out how to bring it into the market space. Whereas most of my career was the opposite direction. It was kind of what we were selling dictated the business. We didn't have a really strong sense of why. And so that was one of the pieces, and I've become a really big believer in I think for companies really instilling that sense of why. And so that was one of the big things for me. I found that it was incredibly motivating for the business, created incredible alignment across people. Like people were there because they bought into the why of the business, not the what of the business. We weren't there to just make some money. We were there to actually profoundly change people's lives by introducing entrepreneurship and making commerce better. And that created incredible organizational alignment. And you saw people go up and beyond constantly, not because there was some kind of financial incentive, but because it was part of the ethos of the business in that sense of why. And so I think that's very profound. And when I look at companies today, particularly younger companies, it's always one of the things I'm looking for is do they have a really strong sense of mission and a strong sense of why in the business? But Shopify had it in spades, and it was kind of based around or led to that engineering focus of the business. And so that one, taught me a lot about creating alignment in a business and just creating very, very strong culture.

Yeah. Every company says that they're mission-centric and trying to figure out if it is real or not is definitely a challenge. So I want to double-click on this concept of thinking long term. So how did you operationalize that? So many of us are built to think in quarters. We have our pipe going into a quarter. We have our headcount plan thinking 1 or 2 quarters out, but like we are inherently short-term animals in many ways. And so how did you adjust to a more long-range mindset and how did you operationalize this, especially for new leaders joining the business and your senior teams?

It, um, yeah, I'd like to say I was great at it. Um, I probably have more examples of failure than I do of success, Kyle. I think so. A couple of things I kind of learned through the process. One was testing this in my mind to see if this is true. I don't think I had any of my senior leaders on variable either. And so one is I wanted to create alignment across all of us when we got together to think about the business. We were aligned in how we thought about it. So that was super important to remove that obvious tension you'd create of like, hey, I want you to think long-term about something, but they're focused on what can I do to benefit the business or specifically benefit me to hit my sales number in kind of this quarter. And so that was kind of number one. Number two, I would take my senior leadership away and we would try to really get away. Rent an Airbnb in the woods somewhere and just kind of hang out for a couple of days. And we specifically tried to avoid these really linear agendas of like, okay, we're going to talk 1 hour about sales process and we're going to talk 1 hour about our marketing alignment. And rather, we would ask really large existential questions. And I remember we did one, we had everybody together and we had our first session and I just opened it. I said, okay, we need to rebuild this business. We have no salespeople. How do we do it? How would you go to market and compete with Shopify? You weren't allowed to hire a single salesperson. And it led to this really interesting conversation that suddenly bubbled up all of these tangential ideas we hadn't thought about because we were a sales organization. This is how we think. It's how we're wired. And by stepping back and kind of asking these really big, broad questions and giving— I think we spent like 3 hours noodling it through and challenging ideas. That was really important. So doing those kinds of activities where we could actually try to step back and step away from it. So those are probably the two biggest. I'd say maybe a small third on that was we tried to spend— so I'm back up on this one. One of the challenges of a big company is it's easy to get somewhat siloed in your business, right? We're the revenue organization. Here's what we do. So we got sales and marketing solution, and we know our world really well. There's a domain, stay away. We're really good at this stuff. Well, product's doing the same thing, and you got marketing doing the same thing. And so bringing those others into our business and inviting them in, like, hey, we want to hear from the VP of engineering who— Shopify Glenn, he's brilliant. Glenn, could you join us for just 90 minutes? Just talk about how are you thinking about commerce today? What are the types of things you're thinking about for the business? Again, mission like very long-term product-centric. Like, how do you think about it? What do you think about the next 18 months? We found that very— it was kind of eye-opening for all of us of just like helping to realign ourselves around where is this business going? What are we really focused on? And are we building something that's long-term and aligned, or are we getting too focused on short-term metrics and just trying to achieve a quarterly number?

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Yes.

I don't know where he got that from, but I just attribute it to him.

Yeah. I found similar, I think in my early days when I was young and full of piss and vinegar and needed to conquer the world, I struggled with dealing with engineering was so frustrating. You ask a simple question, why they just can't ask, you get a 20-minute explanation back. It's like, give me a simple answer. And I really came to appreciate especially Shopify had some, and still does, has some brilliant product leaders, product directors, engineering leaders. They brought, certainly compared to the way I think, just a very principled, methodical, very reasoned way of thinking about a problem and thinking about an approach to things. And I gained a lot of respect after spending more and more time with them, gained way more respect and way more empathy, I think, for what it meant to actually be a product director, an engineering leader, and what to me seemed really easy. Why don't we just change an API element and just 5x it? All of a sudden, they're exposing like, well, here, let's talk about what the actual and how it actually operates and just gaining an understanding and respect and empathy. And by the way, I think on that, talking about this broad kind of creating alignment, I think when they saw me trying to understand what the root problem was and spending the time sitting down at lunch for half an hour to just listen to them and talk about the challenges of scale or why checkout gets throttled at a certain amount. I think that gave them much more respect for me then as a leader, actually trying to understand the problem and find creative solutions versus just walking in and demanding what I thought needed to happen in order to accelerate a part of the market.

Yeah. So let's double-click there. So what were the key lessons you learned to be a great partner to product? So spending time to understand their world and root root problems as well.

Clearly, I think, and by the way, that's a subtle thing, but pre-COVID in the office, we'd have lunch would be 12 to 1:30 or whatever. I would specifically at least once a week make an effort to try to find an engineering leader and sit with them because it was really common. All the salespeople sit together and the marketing people sit together and et cetera. And I would purposely go try to find an engineering leader and just Talk to them, just try to learn. Hey, tell me about, like, I'm trying to understand, you know, hey, we had an outage. What happened there? Or, hey, like, you know, this product we're looking at developing, like, what are the big complexities to it? Or what do you think the big unlock will be? And so that was number one. It gave me, number one, you just get to know people so you're more comfortable in their organization. You show up and everybody's not awkward when you're there. A lot of two-way conversations then open up. They would start expressing interest in commercial. Like, tell me about the customer. Like, What are you doing and how does that work and why are we struggling in certain areas? So that was hugely beneficial. I think, you know, we talked about this sense of why in the business, having an understanding and really respecting that. So when I'd come to the table, I always had to keep in mind, like, they're mission-driven and this is the mission they're focused on. And so I think with that, the asks I'm bringing are the things that I think we need to do as an organization. Are they aligned to that? Like, am I thinking short-term, I'm trying to win some deals, or how are they going to perceive this? Have I thought through this well enough to build the business case that actually what I think we need to do and, you know, the specific feature set or whatever that I want to talk about actually is aligned with this mission of we're going to make commerce better for everybody. And it's an 80% problem that merchants have. So those were some of the pieces that I learned at Shopify were important. But you know what the root of it meant? It was like relationship. It was serious, lots of time with relationship. And I think early in my career, I'd failed at that. I just showed up with my demands of what had to happen because we're a sales organization and you want me to sell, then go build this thing. And so it was a lot of time just getting to know them, understand them, try to understand their world a lot better that really played out and paid a lot of dividends over the long term.

Yeah. And I think the subtle change there that you're getting at is every roadmap ask or piece of product feedback being rooted in the customer first. And it's a new habit to build as a revenue leader because we always want to say it's 12 customers at $75,000 ARR a piece. Like, that's the framing a lot of the time, as opposed to— like, that's not how a PM or an engineering leader thinks.

Totally. One other thing actually that was super useful was particularly when you had, you know, I can think of a couple examples where we had a merchant or an opportunity open up that was really interesting for the organization and, you know, didn't need necessarily custom feature set, but maybe we needed to accelerate our roadmap in certain areas. It was going to cause some pain, but, you know, we believed the merchant was worth doing it, like the name brand recognition or credibility would create in a new territory or a new region or similar. And actually bringing the CTO or bringing the VP of engineering to spend a couple hours with a customer just to learn about their business and talk about it was incredibly helpful, not only to create empathy both directions, but what I found was it humanized a lot of the problem sets that the engineers faced. It wasn't just a theoretical whiteboard exercise of like, oh yeah, you know, when a merchant's trying to do this, it was actually sitting down with the merchant, listening to them talk about like, this is what's happening. This is the pain. This is the, fraud or the lost deals or whatever it was causing in the business. And so that was incredibly beneficial. And in a few cases, did actually move the needle of, okay, we should accelerate the roadmap and I understand the problem set. And especially for engineers, they get super excited about complex problems. And so putting them in front of a customer with a complex problem got them pretty jazzed up.

Yeah, check out Code Red as the most interesting story, I think, there. Because, you know, obviously the Plus organization would be banging their fists on the table for more flexibility in checkout, but it wasn't until it was put in the customer voice that it was actually like Toby down. It was like, excuse me, what are customers doing? Customers are hijacking our checkout to go do something else because we're not giving them what they need. Like, that's like, we can't have, we can't put a customer into that position because our product is deficient. And all of a sudden, boom, overnight, you know, they, they declared a code red, swarmed that problem, and all of a sudden it got better. And now checkout is this like insane competitive advantage for the company. That, that was a cool, that was a cool thing for me to witness.

Yeah, it was fascinating to watch a large company like that move that quickly and, and dedicate resource like I'd never seen before. It was wild to watch.

Yeah. And that happened at an all-hands, right? Somebody asked an AMA question about it and that's what triggered it all.

Yeah. It triggered a view into— yes, it was a question that triggered an exploration into a problem set that hadn't really been exposed that suddenly led to a, oh, we do actually have a real problem. And this doesn't make any sense. It just does not fit the ethos of the business, the way we think about things. And yeah, Code Red was called. One of our most senior engineers was put in charge, given unlimited resource. He could pull any person from any team anywhere in the organization. It was a 9-month sprint to recreate it, and they created arguably the best checkout in the industry now.

Yeah, I don't know how much argument there is there anymore considering the data. So we talked about how to build those product relationships. Let's double-click on influencing the roadmap. So how did you go about getting things onto the roadmap that you really thought needed to be there? So certainly rooting in the customer, bringing product to the customer. Any other big lessons on how to influence engineering?

I would say for myself, I think frankly, Kyle, that probably encapsulates. I think the only thing I'd probably add or put a finer point on is I think for myself being this kind of like fast-paced, action-oriented, I've got to get my quarterly number. I think previous to my career, I showed up much more demanding. This had to happen. It was obvious in my mind what had to happen. We're a sales-led organization. Of course, we need to do this. Suddenly being an engineering-led organization where those tricks didn't work anymore, spending the time to actually think about why is this important and does this actually strategically fit into the long-term roadmap of the business? And spending time actually understanding what is the roadmap for this business and hearing from the product directors. And we often talked in themes, right? The themes we were— these are thematically the 4 or 5 things we want to tackle over the next year, trying to really understand that and then use that to speak in their language that would align with those things. And it was good. At times, I'd come up with something that I thought was wicked important. And when I really sat back, was like, no, this is completely a one-off, doesn't fit into a theme. I can't make a good economic justification or an engineering justification that is going to help more than a handful of merchants. And while it might drive my number, drive a lot of GMV in the business, it's really not aligned with us as a product organization. I need to step back off of it.

Yeah. I think a lot of VPs of sales and CROs would categorize product and engineering as not listening, not being cooperative.

Yes.

And if you really step back and think about it, it's because we're speaking about— speaking using totally the wrong language without doing the work to seek to understand first. I think that's a real—

Yeah. And often talking timelines, they think in quarters and years. We think in weeks and months.

Yeah. Okay. Last question on the product-centric company topic. How did you get sales accepted? Because sales was a new thing for the company at the $200, $150 million mark. So a well-established culture and business that was now learning to have a sales org and collaborate with it. What were the key moments in getting sales accepted as a function in the business, one that could command some respect? Any lessons there?

It was a long unfolding journey. Still not sure it's accepted, but two things I think played out there. One was it is just a lot of time. It was a lot of time going to Ottawa, walking the hallways, meeting people, you know, helping them understand what you were building, why it was important to the business, helping them understand that, like, we're not misaligned from the rest of the business. Like, we buy in the mission of the business, we buy into the why, we buy into the long-term vision of making commerce better. We just need to now focus on merchants that don't understand how to acquire the software and don't understand where they should use it. And so it was a lot of walk in the halls, a lot of conversations. The second was And Loren was really good at this, was he'd remind me again and I get frustrated. I'm like, we've already talked about this. They forget everything. And he was like, yep, you got to remind them again and again and again. And so he would spend tons of time with the executive just storytelling, just reminding them again, like year after year. Here's why we exist. Here's the problem set. We're dealing with merchants that they just don't think we're the best product yet. So we're going to have to go talk to them about it. We're going to have to convince them. And he told that story again and again and again. And so that was the other one. And I'd get super frustrated. Like, I told you once, why do we need to have this conversation again? And it turned into like every quarter, yeah, you're having the same conversation again. So it was a lot of that and it took a lot of time.

Okay, cool. Perfect, perfect person to have this topic on the docket. So this is great. So we're going to transition to talking partnerships. So partnerships is a huge part of Shopify's success. Both in the core part of Shop and Plus and everything else now. But it is also all the rage in the market. People are trying to call it nearbound and ecosystem-led growth and better together is being said ad nauseam. Like, it's definitely in the water, especially as companies try to find a more efficient go-to-market. And the promise of partnership is it's a much lower CAC, higher quality deals, stickier, longer retention, higher LTV. And there's so many more partnership technology providers that are banging this drum constantly, two of which have just partnered up in Crossbeam and Reveal. But I also see partnerships go wrong so frequently. And this big dream with all this effort lead to pretty little return. I have some hypotheses. I'd be curious, what are some of the big, most common mistakes you see people make when they're setting up a partnership program? And we'll maybe talk about this from your experiences doing Fractional and some of the— what Chop did well. But let's start with the downside case, like where does it go wrong? Why are people not getting the return?

You're right. It's interesting that the, it's been a very common theme the last couple years of almost every company I talked to is interested in partnerships and how do I create, you know, an agency partnership or a technology partnership. And every company pretty well that I've worked for has had some form of a partnership organization. And I think arguably Shopify is one of the only ones that I saw work well. I think when I step back at it and in reviewing some of the companies, you know, some that I'm working with and others that I've just talked to, one of the things that I see straight out is companies get super excited about partnerships for all the reasons you mentioned. So in their mind, it's super clear why I would do it. If I could partner with, you know, Citibank, oh my goodness, they've got 500,000 small businesses and we get access to them and they're going to put us on their portal and oh my God, like maybe they'll put us in an email, we'll get a logo in there and if we could get— and then the classic math starts, right? If we can get 1% and et cetera, right? And every investor presentation for the last 30 years begins with that, right? It's a $48 billion TAM. If we can get 3%, the problem is the if. And so I think to get down to the root of your question, one of the things I find every time in looking at partnership programs I created that have failed at was I didn't actually step back to take the time to really understand why the partner cared about it. Like, what is their win for this thing? It's easy for me to get excited. I can see all millions of benefits and what I'm going to get out of it. If there's not a really compelling reason why they care about it, and not they get 10% of the, you know, ARR for the next, you know, 10 years, like, that's not it. They're not there to, you know, most partners and channel partners are not there to build a business so they can get 10% of ARR for someone they refer to you for the next 8 years. They're building a business specifically to accomplish whatever. So how do you actually impact their business? And if you can't answer that question well, here's how I help them acquire customers. Here's how I help make their product better. Here's how I, you know, 1 1 3, whatever it is. If you don't have a really compelling answer to that question, 99 times out of 100, you're going to fail. Partnership will work. Everybody gets excited. You'll sign documents, you'll put logos on each other's sites, you'll do some kind of high-level integration, you'll figure out a rev share model. Nothing will happen. I see it again and again. And so a good example, Vision Critical, I leaned in, I wanted to build an agency program. I saw all the reasons you mentioned was global distribution, lower CAC. I could get customers in that didn't understand the product and the agency could take it off my hands. It was going to be awesome. and I had agencies who were willing to do it. The problem was the core value proposition we brought to the market was, hey, end customer, you don't need expensive agency to do this. We make it easy, simple. You can do it yourself. Here's all the traditional SaaS value props. Well, that's counter-aligned to what an agency is looking to do. And so we had agencies that would sign up as a, like, just in case, but then ultimately would do nothing with us. And I never stood back to say, like, What is their win? Why do they want to do this? How am I helping them build their business? So I'd say that's probably the single biggest, Kyle. If people don't, if they can't answer that question well and really understand how they're going to help that business add an incremental 10% or 20% growth in a given year, it's probably not going to be a successful partnership.

And you got to be honest about that. I think people will tell themselves stories about Well, we're going to help them doing X and Y, but don't quite put themselves in that CEO or head of revenue shoes to say, is this actually that helpful? Yeah. Great.

We're going to do a webinar. I'm going to stick your logo in our newsletter. Is that really going to move the needle and stand the test of time, or is that just a short-term marketing tactic that we could do without a formal partnership?

When's the right time? Like, I, I, I think, uh, I see companies maybe do this too early when, like, why would a partner company care? Like, you're $7 million ARR, you've got 75 customers. Like, what? Like, why bother? Do you have a thought on when the right time is to think about channel or technology partnership? Maybe those answers are different.

Yeah, that's interesting actually to break those out. So I think for, I mean, certainly the most obvious is if you haven't figured out product market fit and you don't understand your go-to-market dynamics, like, forget it. There's no way you're going to push it down to a partner and get them to figure it out for you because they're less interested, less motivated, not spending the day in the problem. So I'd say that would be your first obvious. I think the second is you know, you made an interesting comment of, you know, like a $7 million ARR. Is that the right time? Like, when do you think about doing it? Um, I think you need to understand the market, and I don't think you necessarily need to have scale in the market, but you need to be really clear on what your ICP looks like, and you need to really understand that target market well and why they're going to buy it. And I think if you can answer that question well, I don't think you need to necessarily have scale to build your channel. From a distribution perspective. But if you're still not certain about it or your ideal customer profile or target segment is a little fluid, or the agencies or the channel partners you want to work with perhaps aren't specifically dedicated to it or maybe cross over lots of different boundaries when it comes to segments, I think you're going to struggle. So I think those are probably the kind of the two keys. The product side is an interesting one. I think I'll give two responses to it. I think one is you need to understand what you are as a company. So are we a platform or are we an application? Because I think the answer to that question will dictate what your strategy's going to be much differently. If you're a platform, you're probably going to be thinking about how do you build your partner program much earlier than if you're an application because platform somewhat predicated on having lots of different technology extensions to allow you to do all kinds of different things and people to build on the backs of you. When you're an application, I think that changes it. And in which case you need to really understand what is the purpose of the product partnership? Is it we're augmenting technology we don't have? Is it potentially opening up a whole new feature set that we're never going to build that's tangential to us and outside of our kind of core focus, but is in the eyes of our customers, maybe super important. So I think you need to answer those questions and then, you know, you get the obvious, like, do we, you know, build or buy or partner this kind of thing? So yeah, it's probably not a great answer, but I'm not a product guy.

Yeah, I think that platform versus application piece is really interesting. And if you're an application, whose platform do you plug into and make better legitimately?

Totally. Totally.

And again, it comes back to honesty. Do you really make that platform a lot better, or is this sort of a nice lie that we tell ourselves?

Yeah. And do you really— when you look at the platforms themselves, does the platform reasonably play in the market you're going after? And I see way too many times where we haven't answered the question well, or to your point, we lie to ourselves. It's like, well, they kind of do. Salesforce is really strong over here and they kind of work over here, so it'd be great to be part of their ecosystem. You've got limited resource. We all have limited resource, whether it's time or money or people or energy, whatever it's going to be. And when you spend it particularly on partnerships, because also, I guess the other comment I'd make on that one, Kyle, is I think a lot of companies look at a partnership like a one and done. We sign the contracts, we're going to do a webinar next month. Right on. We're on our way. And one of the things Shopify did really well with partners is they invested a ton of time in partners, a ton of co-marketing, marketing development funds, partner managers spending time educating. I would go out on the road. I'd always try to visit with partners. I would sit with them, talk about business development, help them understand what we were doing as a business, how to work closer with us. It was a big lift and we put a lot of time and a lot of money and a lot of energy into it. And we understood really clearly how agencies would make money on the backs of us that would further their business interests. We knew that really well, and I think those were two things. And so I think that would be the other comment I'd make is if you're thinking of building channel, it's not one and done. You need to think about this as a completely new go-to-market strategy and invest in it properly to see it through.

So one of the heuristics for folks Thinking about when the right time is when you can commit multiple resources and significant time exec down. And unless you can do that and you're trying to fill, well, this one manager can figure it out part-time, you're probably not willing to do it.

That's a great, yeah, I think that's actually, that's, yeah, fantastic summary to it.

Okay. Interesting. What about the question of, like, should I build a partner program? For what companies? Because I think it's so much in the market right now, and there's so much of this promise. Like, all the vendors will say ecosystem-led growth is going to fix all your woes. Oh, digital marketing CAC is broken. Outbound is dead. The only thing you can do is partner. Partner is the right solution for everybody, which is sort of disingenuous, but I get their marketing. If I'm hearing this messaging and thinking I should start a partner program, what are the questions that you should be asking yourself as a business? Should you build it at all? Because I don't think every business is naturally predisposed to working with a partner program necessarily.

I would agree with that. I think, hmm, that's an interesting question. I think if I step back and look at companies where I see partner programs go well, and actually with one of the companies I'm working with right now, I'm stepping back in and relooking at the partner program we've built and why is it working, why is it not, how do we rethink about it? I think some of this relates back to what we talked about, but you need to have a really clear understanding of what is their target customer segment and what is my target customer segment and do we have a high degree of overlap? I think the second one is, and this was one of the interesting things with Shopify, right? When you put a merchant at the center, remember one talk Lauren or Harley or someone had mentioned, we want to be the operating system, the commerce operating system. For these merchants.

Yeah, I remember that.

And I remember that just the phrase operating system was really interesting because it denotes not just like, okay, we're the commerce component, but like, what are all the things an operating system has to do? Oh, like lending and banking and we need to be able to facilitate payments. We need to do checkout. And what about marketing and merchandising and advertising?

And what about accounting and payroll?

100%, right? And so I think that's the other side of, you look at a company like Intuit, I think they've had a really interesting strategy. We've looked at small business and said, okay, we started as an accounting platform. But now as we look forward and we look at the world of a small business, what are all of those problem sets that a small business has and they believe they're in the right position, they should be thinking about solving all of those. Now, that doesn't mean they have to buy or build all of those things, but where do maybe partnerships make sense? And so I think when you understand the problem you solve for a merchant or a customer, where you sit in their kind of priority stack or their day-to-day, it's really obvious then to look and say, and what else is really related to this that is an obvious, like, well, if you're doing this, this is an obvious problem set. And this is where maybe a partnership starts to make a lot more sense because whoever you're partnering with likely is thinking similar and you're, you know, one of the vectors on their org or sorry, their partnership chart of, you know, areas of problem sets they need to be thinking about.

Should every B2B SaaS company be thinking about partner?

I think the obvious answer is probably no. I think every company should take the time to think it through and should have a really informed opinion about why or why not. And I think if they can answer the questions, maybe follow the heuristic you laid out and that we've talked about here, I think that leads to a conclusion of, yeah, this is probably a vector I should explore and put some time and resource into. And we're at the right age and stage. We have the right resource to commit to doing it. But I think if you can't cleanly answer some of the questions we've talked about and it's not obvious as to why a partnership would or would not make sense, then no, you should walk away from it.

And I really liked your point. At about the stage where you have clear repeatability in your go-to-market and stability.

Yes.

Because you can't get a partner motion stood up if you're still iterating on your messaging every 60 days and your ICP is still shifting. I think that's an interesting—

Yeah. If you haven't figured it out, there's no way they're going to figure it out for you.

Okay. What other advice would you give to companies that are setting up this Setting— let's talk about channel.

Sure.

Setting up a channel motion, like, what do they need to know to make this a success? Say they've checked the box, they have sort of a stable go-to-market, they know their ICP, they found a partner that does have a natural overlap, and they're ready to put in the resources. So we've checked your boxes.

How—

what advice do you give them to make— help them be the most successful?

Yeah, I think Be really principled in your approach. So what are your principles for partnering? What's going to guide your partnership? What are the attributes of a good partner? What do you want to see out of a partnership? Understand that really well. What does your customer get? What do you want the customer experience to be like? You got to think through all those sub-things. If something goes wrong, who are they calling? What's going to happen? So have that laid out in advance when you come up with your, you know, let's call it your target list of potential partners you want to work with. As you talk to them and as you work through understanding their business, your business, where they overlap, all that kind of stuff, go back to that and use that kind of principled guide as your checklist of like, can we answer this question well and does it fit with what we said that our gold standard looks like? And if it doesn't, walk from it. But you need to answer those questions and be principled and stick with it. I think the last one is then understand as a business, how you are going to support and how you are going to invest in that partnership and get beyond the fluffies. It's nice to do logos on sites and press releases, and maybe we'll do a webinar, but actually get down to the details. And I am a firm believer that a small handful of partnerships you can go really deep on and build good relationships with is way better than we're one of 500 logos on a website and I've got 500 that look like that. So yeah, I'd say those would be my top thoughts on it.

And how important are the rep incentives? Is it more important that there's strategic top-down alignment, or do you see the rep incentive for the person actually in front of customers being the key driver?

Can you ask that question differently? So when you say the rep incentive, you mean on our side or on the channel side?

Usually a financial Usually a financial incentive for the partner rep. For the partner rep.

Right. And this is where— so that's a great question, and this is where it gets very challenging. And so one of the things that I've commonly tried to do is, hey, how do I— I will pay an incentive to your rep's channel partner in order to have them promote the product and sell it and push it. Like, let me actually take that off your plate. I'll do that. I'll invest the money. And this is where that— back to that alignment question, how are you building their business? Because 9 times out of 10, I've had huge pushback from the CEO or the CRO saying, hang on a second here. Now you are incenting my reps to build your business. I'm incenting my reps to build my business. And if your business can help do that, great. But hang on, the moment we get an incentive involved, back to where you and I started this conversation way back when on, like, is variable even a good idea? The moment I introduce any kind of incentive from an outside organization into my organization, my rep's really thinking about building my business or they're not thinking about building another business. And so this is where I think it comes down to why is the rep going to care? Because you're going to help them close more business. How are you going to do that? Because you understand really clearly what you bring to them to make them better, to help them grow their business and win at whatever game they've set out.

You've made their solution better by being more complete.

So it's 100%.

It's about 100% building the customer.

You're helping them close business that benefits their company.

All right.

That's awesome.

All right. Let's transition into a quickfire. So I have 4 standard questions. I'm going to insert a bonus question because I know you. So I've never been around a leader with the unequivocal followership, like the sort of unimpeachable record of The perfect Q rating. Like, everybody who's worked for you will almost immediately say, Berg's one of the best guys I worked for. Like, it was, you know, he cared about me, he helped me get better. And I've never seen the same followership. Like, you're the number one on that Mount Rushmore from folks that I've been around. What? And we could— I thought about doing a podcast. I thought about doing the episode on leadership, but it's just too squishy and it's too much out there. But you would've been— maybe we'll run it back and do that one later. Where does this followership come from? What do you think you do different than so many that has led to sort of the perfect Q rating here? And I know you hate this question because you're a humble guy.

I do hate this question. I know if I'm a humble guy, but I do hate this question. Thank you, by the way, for the kind words. Gosh, man, I should probably ask you. You're one of the guys that worked for me, but In fact, I'm going to ask you, but one of the, I think when I look back at it and I learned this, I think too late in my career, I had this idea that I was the EVP of sales and I'm the head of revenue and I'm the insert fancy title and I needed to have the answers. It was my job to tell people what to do. And the reality was, it's like, I don't know, man. I'm facing problems day in, day out that are new to me. I don't have the answers. I got good instincts. I've seen some things, Most importantly, I've got a great network that can help me work through problem sets or maybe have seen problems I haven't. And so, one of the things that I learned way too late, I think, that's a real superpower for leaders is vulnerability and just being able to say, I don't know. I don't know the answer. Here's what I think. And I think we have this idea we have to be bulletproof, and I think people just see through it. I know that the leaders I have worked for in the past where you're dealing with their ego or you're dealing with this false sense of who they are and you just don't know who they are, and as a result, you don't build trust with them. And so I'd say it'd be number one. I think the number two is I'm just a big believer in people. And so I think a lot of people enter into a relationship where you got to prove that you're worthy of trust. And I find my default is I'm just going to assume you're here to do good work. You want to do good work. You're not here to screw around and have a job that's mediocre and feel like you're not really contributing. You want to work. And I've screened for that on the way in. I hired you for a reason. And so I'm just going to believe that, and that's going to be my default. And so I'm going to trust you when you come back and tell me something's not going to work. My default is, all right, I'm going to trust you on that. Now let's dig into it and find out why. And as we go through, we'll maybe uncover something different. And I think also, when I see a rep falter, they miss a month, miss a quarter, my default is not like they're out. My default is usually, that's really weird. Like, what changed that suddenly they're struggling? Is this something personal? Is it I haven't trained well? Is it they don't understand the objective of the business? Let's start there and work our way back to, no, they're just actually not well suited to the job. And so I think people see those things. They understand you're in it for them and go for it. That's not really lightning kind of round, but yeah.

So that second piece is one of the biggest early lessons I took from you, and it was within our first, like, 60 days. At Fish and Cradle because I came from a boiler room. I came from like a hire 10, 5 will work out, like turn and burn type of old school environment that I had to unlearn. I'd been reading a lot about leadership and I had formed a different opinion, but I'd never seen it in practice. And certainly early in my— I can't remember the words you used back in the day, but this like default to trust was something that I— it's in my operating manual. Like, I call it my blueprint. A lot of folks have it like, here's the blueprint of working with Kyle. And one of those things is like, I'm going to default to trusting you first, and then something may change that. But yeah, I would agree. I think the other thing is you never bullshitted anybody. Like, you were pretty straight up with folks and spoke plainly, whether it was good or bad. And I think it's one of the most challenging things for sales leaders is we're trained to persuade and spin and influence. And so we have that instinct for our people. It's like, oh no, your quota going up is actually a great thing because like, whatever. And as soon as you do that once or twice, then people are like, oh, obviously I can't trust anything this person says because they're spinning me. And I consistently knew that there was no spin from you.

Thank you for that. We've all worked for the leader where you've learned, you know you're getting spun, you know you're getting some kind of messaging, and you just instantly don't trust. And it leads to a culture of, what do I trust around here? Can I trust anything? And so I learned really early with org changes in particular, transparency is wicked important. You need to communicate a lot. You need to help them understand why you're doing it. And yes, be honest. Just tell people the truth. If you don't, not only do they know they've not been told the truth, but now they can't trust you. And that's super corrosive.

Yeah. Okay. Now the real quickfire. All right. What do you wish you knew as a new leader? So your first time in a second line, more executive leadership that you only came to understand Probably.

Yeah. Power of vulnerability. We just talked about it.

Okay, cool. What's the most common advice you give to your leaders or mentees?

Probably increasingly now, which I wouldn't have given earlier in my career, but increasingly now is, do you really understand the problem and have a good handle on it? And do you really understand what you are trying to achieve. Yeah, I think those two things are missed too often. We solve for the wrong problem or we solve— yeah, we solve for the wrong problem.

Yeah. I can't remember who the author is, but the quote I love is, a problem well defined is half solved.

I love that. I know you always hear, this is not quickfire. You listen to engineers talk about, like, you fall in love with the problem and I spent hours thinking about the problem and I've never done that. My extent of the problem is 28 seconds and I've got the answer and let's move forward with it. And then realized many, many times I solved the wrong problem or I solved a problem and created 17 more downstream that I didn't think about.

Yeah. Or a problem, but not the most important.

Yeah. Great one.

What's the hardest lesson you've had to learn? Oh, interesting.

Probably understanding myself. Shopify invested in coaches, and I'd never had a coach. I thought it was for kids and silly and people who don't understand themselves. And I met a coach that really resonated with me. And when I would bring problems to her and it was always like, I can't figure out, like, so-and-so is being a dick and it's their problem. And 9 times out of 10, we would sit there and at the end of the day, it was like, why do I feel that way? Why am I reacting? What is my triggers? and it's been unbelievably valuable for me. So I'd say that was probably the hardest lesson to learn because there's a lot of difficult self-reflection that goes into it.

Yeah, that's a great one. Last question. What's the best thing you've read in the last 12 months?

Ooh, best thing I've read. You're going to get disappointed because you read so many business books. At Christmas, I was given— it's called The Master and Margarita. It's by— I'm going to screw up this guy's name— Mikhail Bulgakov. Was written in 1940s in Russia, Russian author. And it's this fascinating, really wild, vivid kind of journey this person goes on. But there's a lot of, like most Russian authors, 17 layers deep of culture and government and a million things inside. And it was a fascinating read. Really, really good book.

Cool. Nice. This did not disappoint. I knew this would be a good one, and it was great. I think there's a couple really big takeaways here. Understanding what's in it for the partner is one that definitely stands out and some of the timing around when it makes sense. And then being successful with partner, really starting with empathy. Like, I think we came back to that empathy point a number of times. And so that, that is hopefully one that folks will take away. Where can people find you? What do you want to plug?

So I'm not on social. I can do a whole rant on socials, but I'll leave it out. LinkedIn. So that's usually where I am. I don't post a ton. I post a little bit, but I am on there. People reach me that way. That's it, Kyle. And I guess this, I guess this podcast.

Yeah, there you go. And if you're a late stage, if you're a late stage B2B SaaS company, you got cool problems to solve.

That's right.

Million plus.

And if you're a 70-year-old executive at some boring old company, you know exactly how to reach me.

Yeah. Awesome, man. Well, thanks for joining. This was great. Appreciate your time as always.

Right on. Good to see you, Kyle.

Thanks, brother. Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe and you can You can find a link in the show notes and be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.