Overcoming Market Challenges by Connecting Product Signals and Sales Opportunities

with Dakota McKenzie,

Revenue Leader at Endgame

In this episode, Pete is joined by Dakota McKenzie, Revenue leader at Endgame. The two discuss revenue challenges in the market, tactics for selling to today’s customers, connecting product signals to sales opportunities, and more.
Play Video


Key topics in today’s conversation include:

  • Biggest challenges in the last few quarters as a revenue leader (0:44)
  • The one thing to get right in 2023 (5:16)
  • Speaking the language of today’s customer (7:20)
  • Dakota’s journey to becoming a revenue leader (9:18)
  • What is the context for Endgame’s hypergrowth? (14:40)
  • Current growth challenges in today’s climate (19:55)
  • Final thoughts and takeaways (22:41)


The SaaS(ramp) Podcast explores how tech leaders scale from product adoption to enterprise success. Learn more at www.saasrampmedia.com.


Pete Thornton 00:06
Welcome back rampants to The SaaS Ramp Podcast. I’m your host podcast Pete. Special guest on today we have Dakota McKenzie, revenue leader at Endgame. Excited to have you on today, Dakota. Welcome to the show.

Dakota McKenzie 00:19
Thanks for having me excited to be here.

Pete Thornton 00:21
It’s awesome. I’m excited to have you on just based on what you guys are doing a little bit of the background that you have, just because it’s similar to some other folks I’ve spoken to and like, all seem to be doing some interesting things after your previous experiences. So we would kind of like to jump into the deep end. And I’m sure it was top of mind anyway, just being a revenue leader in this kind of fast growth company. But the last couple of quarters. What’s the biggest challenge you’re facing as a revenue later?

Dakota McKenzie 00:50
Yeah. Look, the markets have been tough, the last couple of quarters just in general. And it’s funny, if we all remember, last year, a few quarters back, we had incredible highs. The point where like all teams are ripping, everybody’s flush with cash, we’re all hiring, we’re building tons of teams. And we all know like we’re starting to see major challenges just in the market. So that’s teams reshaping and restructuring. Sometimes downsizing, unfortunately, yeah, buyers are slowing down their processes, tightening their belts and being really disciplined in what they buy. And so I want to start with this, because I just want to acknowledge that’s the reality for many elite sellers and amazing companies in this market. And it’s not, of course, you know, you want to be able to control your own destiny. But there are factors that are major challenges for companies. And so I think like for us, you know, a major challenge for us as a business is like kind of what I shared, but also creating a new category, right. So it’s even more important for us as a business to tie to outcomes, real business value. And really move focus in areas that move the needle for our prospective customers and our existing customers. And so what we hear from everybody in the market prospects and customers alike is they’re trying to become more efficient, resilient, productive. And I couldn’t think of better words to describe the team at endgame and what our team is really committed to to make our customers successful. Our obsession of trying to help our customers achieve and achieve meaningful outcomes, why we’ve landed some of the best product lead growth companies to date, and why we’ve done such a great job as a business so far. So that said, we’re also asking companies to fundamentally change the way that they sell, and the way that they think about this, and that can be intimidating to sales leaders and operators of these companies that are trying harder than ever to hit their numbers and be more successful. And that makes this challenge hard. But it also makes it really exciting. And why I’ve really loved being here. And so we’ve done a great job, and we’re continuing to grow with empathy, and making sure that our customers can be successful, but being really thoughtful in that process.

Pete Thornton 03:00
Yeah, yeah. So I mean, not ignoring the economic climate, and maybe it’s not affecting your specific business, but it would affect your buyers, which is, of course, your specific business or your portion of the team anyway. So that’s, that’s like 100% a reality. I just saw there was a call I was on a few hours ago. And I saw a nice graph delivered by the postman CFO, and it was just showing market trends, like nothing to do with the company, like just market trends. And so he went back several years, like all the way to Oh, seven even he’s, so look at this. And this was a great history lesson through economics. And it was like, it just showed through this Oh, and then it came back into where it previously had been. And it was like, so was like the 2021 anomaly, and we’re back to like ground zero? Or is this, you know, this, here’s what we’re trying to predict where we’re going based on these specific trends, etc. And so like that, that is a reality. And people are kind of transitioning backwards into a little bit more predictability and efficiency. So yeah, if that is, if you are already there within your organization, fantastic. But a lot of people are making a pivot. Are you kind of saying like you were already centered in that space and not necessarily having to manage messaging or anything like that?

Dakota McKenzie 04:19
No, I think we definitely have to manage messaging. I’m by no means the person who’s going to predict the market. But I do think that there’s a focus on controlling our destiny where we can and being really thoughtful around what’s changing in the market. And collectively, like being all hands on decK as a team working with the executive team or an end game working product team, aligning the customers better understanding doing workshops and things of that nature. I think as a seller, you can only control so much and so we want to focus on the things we can control and not throw our hands up in the air because the markets are difficult. So

Pete Thornton 04:55
yeah, okay. So it’s still air shortly but not right By the way, so like for some context for anybody else, we’re early summer, you helped me set up. So that’s when the recordings happen. And so the context for that is sales leaders are probably planning for fiscal 20 years. 23, like looking ahead, at least in the next calendar year. If you’ve done that, I don’t have to be detail oriented. But if you have done that, as a sales leader, have you come up with maybe a single thing or a few things? It’s the exercise of trying to get it to one. But one thing that you feel like you would have to do as a sales leader or a sales team to get next year, right?

Dakota McKenzie 05:36
Yeah, I thought about this a lot. A, you know, be thoughtful about what I share. I think one thing I really think we have to get right to get our organization to grow properly, as lines of business revolve in the profile of sales, hiring is evolving as well. Hiring the right people is the one thing I think we absolutely need to nail to succeed. And so it’s been kind of an exciting case study and challenging case study to compare the types of sellers from when I think we both started our sales careers, to now, profiles have changed a lot. And so like technical sellers, which I can think about the type of seller for any game, become deeply technical. And so one example that I have, which is pretty funny, but it’s very real is one challenge, we’re one challenge for helping customers solve is AES, no longer needing to write a sequel, I don’t typically see that as a requirement for sales teams, that it’s really interesting. There’s a repeat pattern that I’m seeing with teams like that. And so nailing that is fun, but it’s definitely been difficult. And so I can imagine, you’re probably thinking, like, what are we looking for? And I think we’re trying to find people that are deeply curious and aware of the modern data stack. I’ve seen that requirement on LinkedIn and talked to other VPs of sales who are kind of looking for the same thing. And then looking for somebody who wants to solve customer problems from a point of view as a data driven seller with experience doing that. And so I think there’s like a deeper need than ever, especially if we want to be experts in sales, and hit our numbers, is combining the technical and sales acumen that’s required to be successful as a team. So I think that’s really important. That is top of mind for me right now. But of course, there are other factors that,

Pete Thornton 07:19
Yeah, this is so interesting. So my journey and PLG was so moved from a top down motion into, like, just bottoms up, probably led growth motion. And I think a lot of people have experienced that transition, or some version of it, because these things are like different places on a pendulum. I had noticed the sellers getting pushed further and further into a just more and more consultative space, which is a great thing for the customer. But it’s the fact that there are free museums or self service tiers, where it might have just been a more transactional sale before, like maybe a salesperson would have sat there, even five years ago, and those things are being automated now. So the really ambitious sellers are doing fantastic and moving up market because they’re having these really interested customers, because they come through the whole journey by the time they get there. But if you can’t talk the language with a customer, on a technical side, for just certain ones of them, I know there’s some still up here, that is a bigger disadvantage than ever before. So I’m here in the USA Exactly.

Dakota McKenzie 08:27
And I think it’s less about the need to know how to write SQL or code or talking to deep technical detail like an engineer. But it’s the you know, as we all know, kind of the force management command of the message thing is that audible readiness of when you hear that technical aspect or requirement, knowing how to navigate that objection, or what to say, or how we compare, or how we differentiate, like all of those things really matter. And so that’s more when I mean on the technical acumen. But when somebody also has the technical background and experience to challenge somebody on how to create a category, I think that’s really compelling. And we’re starting to see more of that as well. So I think that’s kind of where I’m combining that technical and sales acumen. But you’re exactly right.

Pete Thornton 09:10
Yeah. Okay, being able to converse, listen for it and kind of get the context clues between the dots. Yeah, for sure. Okay, your journey, you’ve had an interesting journey. We’re comparing a little bit of some of that, like these patterns from some others that I’ve noticed, leave that alone, but I’d love to know, because a lot of members of the audience are in your same seat. And it’s just like, cool to compare notes. And then some are ICS who are looking to one day, you know, become a revenue later. So what’s your personal and professional journey leading into a seat at the endgame here?

Dakota McKenzie 09:44
Yeah, for me, I just have this obsession with building at the earlier stages in some way. And I think you’ll kind of see a pattern, aside from I think, joining sumo logic, which is kind of early but it’s where I learned to become an elite seller. It helped me Get out to the Bay Area where I currently live, that I went to Databricks, I joined as one of the first sellers and top AES globally, I was there from roughly 4 million to 100 million was an amazing journey, learned a ton as you can imagine, then join segment, I was one of the early group on the one of the people that joined the early group of the Enterprise team. So growing strategic accounts, and learning how to maximize ARR for the seven figure type deals. And then I went to unusual places, or unusual ventures where I sat in the seat, working with tons of founders within the portfolio, but actually working with them, you know, quarter over quarter, so my OKRs were tied to their outcomes to the business. So it was able to take three teams to over a million in ARR. And that’s where I really got hooked on the building aspect, like really from the ground up to zero to one piece that led me to endgame, which is another unusual portfolio company, so kind of had the unfair advantage of learning how well the business was doing. And so, I chose GIMP for a few reasons. I am really inspired by how amazing the products are of our customers, and how advocacy for world class products through selling impacts kind of like the adoption of the global wide scale. So how people kind of create the virality of those products like in figma. and things of that nature. I found the endgame really fascinating because it’s solving a data engineering and data science problem that happens to impact sales downstream. And PLG. Companies have some of the most inspiring people in software, if you really talked to how smart some of the sales leaders are in those teams, and faster data driven, and they truly understand how to drive value to their customers. And I wanted to be a part of that market in that journey. And learn from them as much as they hopefully can learn from me along the way.

Pete Thornton 11:48
Yeah, very cool. So yeah, totally get it as far as being a kind of bleeding edge seller for 1,000,200. And most people don’t do that. Don’t do that whole ride right there. I know some others who are having that ride right now, because they started earlier. And they’ll, you know, stay for a long time. But it’s that you go through so many transitions in that time period. So there was that piece. And then the one thing that’s a little unique about your experience, I might see that some are advisors in the past or something along those lines. But you were literally there for two years at unusual ventures. Would you just read the whole for us a little bit more on that says you’re an individual contributor, then head of sales, and then you’re moving in there? Are you giving go to the market like advice, just like contributions, just strategy with some of the various portfolio companies?

Dakota McKenzie 12:40
Yeah, so I think there’s two aspects of it, one can check out the unusual Field Guide, I’ll give it a little bit of a plug on best practices on how to build a go to market team, how to build a business and things of that nature. So we definitely contributed to the content there. But yeah, what was really exciting and compelling to me is that we were in the seat. And so we were cold calling, building outreach sequences, managing pipelines, managing reps on those teams participating in board meetings, tying to a revenue number, closing deals, teaching the founders how to kind of round out their sales, go to market and executive teams. It was one of the coolest jobs I’ve ever had. For sure. I just learned a ton within that process. I think a lot of people think that it’s an advisory capacity type role, and most are from the venture seat. What I think is unusual is that they put their money where their mouth is and really have people committed to the mission of the businesses that they invest in the very unique opportunity. And I learned a lot on how to manage founders and how to manage teams, and reps and kind of understand like how to do the zero to one thing in a more efficient repeatable fashion for however repeatable and efficient you can make that so

Pete Thornton 13:54
yeah, but that’s very cool because you get a couple of at bats at something that people might if they’re going to be a founder only get 123 You know, opportunities, successful or not. To like fulfillment. That’s really interesting. That’s an unusual venture indeed. I really like that piece in this whole life journey. It’s just fun after you look at enough LinkedIn profiles, you know, you’re like you get a sense or a feel by looking at it and those kinds of are the kinds of things that stick out so I’m glad that was as cool as it looks on the Israel paper there. Will Oh a little bit more about the game then. This is what a cool name, by the way for a company like love tech names, love tech, little avatars and everything like that, no matter why she can’t help but just dig it. But what is in the game? What’s the context for hyper growth? Why is it blowing up? You tell us all about it.

Dakota McKenzie 14:51
Yeah, so we’re an operating system for product lead sales, and we help good market teams become more efficient and increase the revenue by just connecting the dots between product signals and sales opportunities. Because these product lead companies have lots of data, and they have a lot of users, trying to find the correlation as to what leads to conversion is really important. And it helps teams more efficiently, prioritize their time, convert the right companies to maximize revenue, things of that nature. And so we’ve helped sales teams use end games to drive hyper growth and find new opportunities. Find Buyers And champions understand their usage, build playbooks take immediate action, all that fun stuff, right. And so the hypergrowth is context for scales, like we’ve just partnered with the best companies. And we tie for our ability to align with their primary goals and objectives, and help them achieve their aggressive revenue targets, really, by partnering with their leadership teams and their reps and really talking to what they care most about as a business, but also sharing what we’re seeing in the market and really kind of tying to that. So it’s been super exciting to be a part of it for sure.

Pete Thornton 16:00
Okay, okay. So, for product lead growth companies, you’ll come in, and then your ability to analyze and gather insights from the data that they have because I’ve never seen more data in my life than at a plg company, like the customer data you have access to. It is not like bombing out marketing, and hoping and praying and finding out, you know who likes it years later, like you have customers, you have business intelligence, etc. So are you linking into some of that underlying data to just try to say, hey, let’s be super targeted over here. What are some of the ways that you know, the endgame ends up supercharging? These companies? Yeah, it’s

Dakota McKenzie 16:39
a great question. So we’re looking at how customers are using the product today, making those users and accounts relative to one another, finding the commonalities or patterns or trends across those accounts. And helping teams accomplish different use cases like converting new trials, increasing conversion, existing customers, cross selling products, or that seems appropriate, looking for expansion opportunities, or upsells. So really trying to whatever the team’s trying to accomplish and looking at how users and customers want to use the product and be sold to and being prescriptive about how teams should do that on their side using their

Pete Thornton 17:20
Okay, okay, very cool. So, I mean, there’s a couple of personas I can think of who would just gobble it up? Is it primarily a head of growth at these types of companies? Or is it more like with the founders, co founders,

Dakota McKenzie 17:35
To grow, growth and sales are the two teams that kind of come together to bring the go to market motion to light at these companies and why they’re doing so? Well, right? The first thing that they do, right is their product or growth companies, the journey is natural for many, as we know, the seller comes in to be more consultative on how to make better use of the platform, tell the right story, or, you know, find ways to expand the revenue within the customers that are getting the benefit of the solutions today. But really, like what is important is that growth strategy is complemented by you know, the sales strategy says,

Pete Thornton 18:14
Okay, okay, that’s excellent. What an interesting thing to be able to do, because you can be in love, touching base with those very interesting up and coming plg companies that are just doing. I mean, it’s just a fascinating model that has been, it seems so logical. Now, as you look backwards, it has been further and further along this journey. But there’s some companies that are doing really interesting things, and it sounds like you will be like the growth engine that fuels their, you know, exponential ascent, basically. That sir. Yeah, so really interesting tie in from what you were doing an unusual venture straight into the endgame then because it’s almost like the software version of what you were doing as a services model before. Yeah, it was all planned from birth. Everybody. You went to college? Right, right.

Dakota McKenzie 19:02
Right. Exactly. Yeah. That’s been my path the whole time. Of course.

Pete Thornton 19:08
That’s it. That’s my harshest thing is I spent so much time in education. And then I got out of education when a student asked me, Hey, when are we going to need to know this? And I was like, good subject. And I was like, oh, never ever probably. And that was when I was like, Oh, I think I’m about to retire. And now we’re gonna have like, nothing, nothing translated. My wife and I have lots of arguments about our seven-year – old son. So I’ll stop here for fun. Well, it’s super cool to be a hyper growth company working with all these hyper growth companies. And it’s just that’s where it ‘s my love. You said, You’re a builder. I really like being on the front end of a cycle like that myself. I just find it very exciting. And this space where you’re at where you have this product market fit, you figured out so much are already helping customers but you’re looking to grow and scale it at that point is a fun location with a lot going on, but there’s challenges associated with it. For sure. So what’s your take on the current challenges of growth that are associated with growth that you’re probably going to have to, you know, bear the brunt of this revenue later? Yeah.

Dakota McKenzie 20:11
I mean, it’s just at the beginning, like we’re experiencing market turmoil, the teams are still poised for growth, right. And so customers and prospects are focused on cost savings, efficiency, and reducing overhead. But that doesn’t discount that anyone’s kind of lost sight of growing their business and trying to make their businesses successful. It’s just a different approach to doing that. And so I think what’s important as a revenue leader is, you know, even if we look like last year, it was growth at all costs. But I think really, what we’re seeing is like, we have to be more efficient and focused on revenue, building a revenue engine that’s kind of suited for the growth targets for the upcoming year. And that requires a lot of planning, and thoughtful investments. And so that also means investing in smarter approaches to growing revenue. And so as a sales leader of end game, like, I think it’s really important for me to think about approaching our customers and prospects, challenges and empathy, just focusing on their teams, how we can make them more efficient and productive rather than kind of pushing solutions down their throats, especially like when it’s a challenging time for a lot of people. And so, you know, with massive user bases, generating tons of data, like sales teams, need to know what those signals are within their businesses. We kind of talked about the value prop for the endgame in finding that within their book of business and trying to drive pipelines to accelerate their deals, to complex and complicated problems, but I think we’re laser focused on that. And as long as we continue to do that, I think it’ll be alright.

Pete Thornton 21:36
So yeah, yeah. Well, that’s interesting, because the data is there, but it’s turning the data insights into data performance, or I don’t know, you’ll probably have a great way to put that. But it’s, it’s taking that and using it leveraging it actually actioning that stuff, which Yeah, I know all the gain is in that aspect. And it is certainly difficult. Like I’ve watched, like 12 member data teams, just take this stuff and toil night and day and try to arrange it and figure it out and make these hypotheses and transitions so that people can make that one final step a little bit easier. A lot of insights come together. It’s, it’s a very, I don’t know, it’s like where art meets science a little bit. It feels like

Dakota McKenzie 22:18
and if you’re experiencing that problem, you can contact us at endgame and we have it out yet.

Pete Thornton 22:24
T yet. Good. Yeah, definitely. Cool problem to be solved for sure. And it seems like you’re in the right seat thereafter, especially your experiences seem to lead right into this role. So it feels like a really good fit. Nobody gets there alone. You know, like, whether that student I owe thanks to for asking me like the question of like, when’s this happening to me? I’m like, never, I’m quitting. you’re tweeting, we’re all quitting. Right? I’ll go to technology now. Or, or somebody actually mentors you along the journey. Do you have two or three people in mind you’d like to thank for the journey. Maybe we’ll mention them. But they’ll mount there in a few weeks.

Dakota McKenzie 23:04
Yeah. So I think one is Ollie from Databricks. Like joining the company. So early, it was such a profound experience. For me, I learned so much so quickly, from machine learning to business building. And I’m just grateful to have worked under his leadership, and first championed me throughout my career at the company and elsewhere. And so I’m incredibly grateful for that. Alex, our CEO, then entrusting me to lead the team, and give me a seat at the table. And he’s a design and product visionary. And I’ve just learned a ton from him as a leader over the last year. And then lastly, my wife, of course. And so she’s been a huge supporter of me, and I’m incredibly thankful for all that she does for me. So it does take a group of people to kind of build that support system. So I’m very thankful.

Pete Thornton 23:49
Totally. Yeah, that makes sense. Those are all fantastic. I have to do a good job of digging these out and doing the right ad mentions later like, see, I’m appreciative. Let’s start with your wife. Awesome, awesome. And the last one’s a little funny. This one’s like more on my side. This is like a SaaS rant podcast, and a lot of different types of personas view either term slightly differently, and especially when you put them together. So the question would be what the SAS ramp mean to

Dakota McKenzie 24:14
you, you know, thought about this a lot. I think it’s really just like what we’re all here to do. We’re helping SAS businesses grow in repeatable fashion as well as they can, right? Share our learnings and just make sure that everybody in the industry is better at their jobs. And, you know, I’m really grateful that this podcast exists. And that’s, I think that’s what it means to me is nice, nice. Yeah,

Pete Thornton 24:35
I love that. That’s fantastic. I appreciate it, like the audience will appreciate it. And what’s to say? This would be like an interesting call to action. It wouldn’t necessarily be to go find you. Or it could be but if somebody goes, Oh, that’s cool. How do I get involved in the game? Is it itself? Does it have the freemium model? Do you have a self serve? Do you come straight in or is it conversation to understand because it feels a little bit more dense than like, you could just try this, like monday.com or something like that.

Dakota McKenzie 25:06
It’s a little more dense. So the irony is not lost on us that we are we do not have a self serve model at the moment, but more to come on that.

Pete Thornton 25:14
Yeah. Okay, interesting. So it’s contact as a contact is or reach out to contact. Yeah, for sure, though, it makes sense. That’s a big challenge to be solved right there with humans. That’s fantastic. Yeah. Thanks, Dakota. Appreciate the time. Thanks for the participation. And we’ll see you out there on LinkedIn in a few weeks here.

Dakota McKenzie 25:34
Thanks for having me.