The following interview is a conversation we had with John Jahnke, CEO and Co-Founder of Tackle.io, on our podcast Category Visionaries. You can view the full episode here: $148 Million Raised to Build the Future of Cloud Go-to-Market.

 

John Jahnke
Thanks, Brett, for having me. 

Brett
Not a problem at all. So to kick things off, could we just start with a quick summary of who you are and maybe a bit more about your background? 

John Jahnke
Yeah, sure. So I’m John, CEO of Tackle, born and raised in Buffalo, New York. So a bit of an underdog in the tech world. And I’m a family first guy. So I’m married, my wife, and three children. We all live in Orchard Park, New York, home of the Buffalo bills. I actually started my career as an SE, so a sales engineer, system engineer, working for EMC, which, it’s funny that se job defines a lot of who I am from a business standpoint, just helping people solve problems. And then really grew into customer leadership roles through my career. And five years into my first CEO gig, which has been a heck of a lot of fun. 

Brett
Would 20 year old John be surprised that you ended up being CEO and Founder of a tech company? 

John Jahnke
Actually, no. This was the job I always wanted. And I knew from a pretty early day I had a job before, and the president and CEO gave a walk in the cafeteria, and I was like, you know, I really like that guy. Maybe I want to be like that guy. So ever since I was in my late teens, I wanted to try to be a CEO. 

Brett
When I was growing up, I lived in Michigan, I lived in Wisconsin. And when I was, like, 22, I found out about this world of tech. I didn’t really know that this world existed because of just where I grew up. And then really just growing up in Wisconsin, Michigan, you don’t have a lot of exposure to technology and Silicon Valley and that whole ecosystem. Where did you get that insight from? Where did you learn about tech from and what inspired you to want to have a career in tech? 

John Jahnke
Yeah, it’s funny. I grew up a computer kid. My mom was really curious we bought a computer when I was really young. I ended up teaching computer class in elementary school because no one else knew anything about had no. I was just curious. I didn’t really think about it as a career then. And then when I got a little older, I actually dropped out of college for a bit. And my brother in law’s best friend was in tech and he needed a lackey. And I was like, hey, I’d be a great lackey. So I took a job working in it when I was 20 years old and that was really my first exposure. And I never knew at the time how progressive the company I worked for was, but were on the leading edge of tons of open system stuff. 

John Jahnke
We played with vmware when it was 10, and I just got exposed to all this new technology and really fell in love with it. Fell in love with the pace of change, fell in love with solving problems in new ways. And that was the exposure point. So I went back to school for business and the rest is history. 

Brett
If you could meet any Founder who’s living or dead, who would it be and why? 

John Jahnke
It’s kind of the cliche answer, but we work with the clouds, so AWS, Microsoft and Google. And I would love to meet Jeff Bezos just because I think it is a really interesting journey that Amazon’s gone on over the mean, but maybe a little less cliche. One might be Henry Ward from actually, you know, really appreciate the way Henry approaches things from a content standpoint. He’s like this visionary and leader in the market with what they do, but he approaches it in a forward writing kind of way. I actually learned a lot during the pandemic from some of Henry’s writings and I’ve never had the chance to meet him and think he’d be a pretty cool guy to meet. 

Brett
Yeah, his writing stuck with me as well. I remember his announcement for the layoffs right in the middle of COVID I believe, and I don’t remember what exactly about it stuck with me, but the fact that resonates, and I do remember something coming from him when he had to do layoffs, it was very powerful. 

John Jahnke
When we had to go through a restructure, I had a list. I gathered examples from all kinds of people and his was one of the examples that I thought about as I was just thinking through how would I approach communicating such a hard message in a transparent way. It’s funny how I’m sure when he wrote that and when he shared it, he didn’t think about the long tail of impact it would have, but it was pretty meaningful. So I actually try to share things in a similar way just based upon those examples. 

Brett
Yeah, it’s crazy because that was obviously early days of COVID And then in the last three years, we’ve seen a lot of layoffs. Practically every tech company has had to go through some layoffs. So it’s interesting that those early layoffs and when founders were open about it and transparent and sharing those with others, that really did help a lot. I imagine when he was writing that there was no one else who was really doing that at that point or no one else at that scale. 

John Jahnke
Yeah, definitely. 

Brett
What about books? So the way we like to phrase this, we got this from an author named Ryan Holiday. He calls him quake books. So a quake book is a book that rocks you to your core, really influences how you think about the world and how you approach life. Do any quake books come to mind? 

John Jahnke
Yeah, there’s a few that come to mind. The first one, when I was in grad school, I read a book. It was the principles of influence by Robert Cialdini. And at the time, just thinking about influence theory and understanding how powerful it could be and just understanding what those powers looked like, that was one of those quake books for me, because I think you learn a lot, maybe without even knowing about influence. And then the fact there was this deep science about the way influence worked was really curious to me. So that was one maybe a little later in life. The Book of Joy by the Dalai Lama and Desmond Tutu is just trying to work through. Like CEO jobs are hard and complicated and it is a never ending pursuit. 

John Jahnke
Ideally, you build a team where you know the least about what every one of your team members do, which is probably the first time in your career you’re in that position. And it can be incredibly stressful and painful. And I found myself just trying to work through how to have the right mindset, how to think about things in a different way. And that book was pretty impactful. Maybe one last one was Endurance, which is the Shackleton story and Nachoha’s books. I always think about anytime I think I’m having a hard day or hard month or hard year, I think back to those early explorers and how difficult it was for them to survive and thrive. That was a pretty amazing book. 

Brett
My fiance, soon to be wife, and I are soon to have our first kid. She’s probably in the other room listening. So I’m glad that you mentioned that. Endurance is one of my all time favorite books and I’m currently making a big push to name our first kid Shackleton. So hopefully she’s listening in and hears that because I’m a huge fan of him. 

John Jahnke
That’s awesome. 

Brett
Yeah. So let’s switch gears now. Let’s dive a bit deeper into the company. So when it comes to the problem you solve, how do you think about that? How do you articulate the problem you’re solving? 

John Jahnke
Yeah, we enable software companies to go to market via the cloud providers, so our platform makes that a business decision instead of a product and engineering problem. And our team helps support customers as they go on a journey to cloud enable their go to market. So what does that really mean? Everyone has some sort of revenue system. Everyone’s trying to figure out, do I do enterprise sales, do I do bottoms up sales? And these clouds have these massive budgets behind them and they’ve enabled ways for people to buy third party software using the cloud budget and we try to make that really easy. 

Brett
Take us back to the early days and can you tell us a bit more about the backstory behind the company? 

John Jahnke
Yeah, sure. So Dylan, Brian and I, we all worked together at another startup called Green Plum. I actually worked for EMC. EMC acquired Green Plum, I joined, helped the company try to scale. And Dylan, Brian ended up being on my team. So we became fast friends back then and always stayed in touch. And Dylan was part of the beta program for AWS Marketplace. And when he was working through that, he was like, hey, I think the clouds are going to change the way that software sold. And I think that this marketplace thing is the initiation point of that. And I think it’s actually harder than it should be for software companies to take advantage of. There’s an idea here. And he came to Brian and me and we talked through that and I was like, let’s go raise a seed round with that hypothesis. 

John Jahnke
And he leaned in first, Brian and I kind of stayed on the outside. And with that seed round, Dylan leaned in first to start to experiment on what a first version product could look. You know, we had a variety of fits and starts, like most early stage startups do, but in that first year, we ended up discovering new relic, who was our very first customer. And new relic was like, if half of what you say is true, we’re in. We’ve been struggling with this for the last six months. And they gave us a po the same day and then were like, okay, well, can we repeat that? And were able to pretty quickly repeat that pattern with about ten other customers over the next quarter and a half. Which really got us excited about what the future potential for the company could be. 

Brett
What did new relic see in you guys? Why did they have faith that this could be solved or this is a problem that they could trust you to solve? 

John Jahnke
Yeah, we’re lifelong b to b sales, customer success, presalespeople. We all have that same profile and we always worked in emerging tech and I think so many people approach this problem as an engineering problem. I need to go build and integrate with APIs from the cloud, when in reality it’s a business model problem. And it’s a business model problem that requires some technology. But if you approach it business first, technology second, which is the way we thought about it, how do we help these companies change the way they sell? How do we help them complement their go to market system? With a cloud go to market infrastructure, were able to approach it totally differently. Again, we didn’t understand how early it was. 

John Jahnke
We were really early and we actually had this unique point of view and we had expertise that didn’t really exist in the market. I think the combination of all those things and then really with your first customers just comes down to executing. We did what we said we would do, we listened to their feedback along the way. We continued to innovate on their behalf to solve problems, and I think that set the foundation. New relic, still a customer to this day. 

Brett
Just so we can understand the scale that you’re operating at today, are there any numbers you can share in terms of growth? 

John Jahnke
Yeah, we’re at 550 customers. We were growing hundreds of percent year over year. This year is a tricky year. We kind of retrenched the business this year as the whole software market kind of went sideways for a bit and have really doubled down on our ICP. But we believe we’ll see $3 billion of transactions through the platform this year. And we work with isvs of all shapes and sizes, from seed stage startups up to some of the largest software companies in the world. 

Brett
This may just be my perspective, but from my view, it seems like go to market has really become a big popular phrase over the last like twelve to 18 months. Have you seen that as well, or was it already a big term? Was everyone already talking about go to market when you guys were founding this company in 2018? 

John Jahnke
I think people have realized that distribution is what wins. Great product is table stakes. But if you can’t get great products in the hands of users in a way that makes sense to them, you’ll fail. And that really all comes down to the way that you go to market. And go to market is also the single most expensive part of every scaling SaaS company. In the early days of a SaaS company or engineering team, probably it’s far bigger than your go to market team. But at some point in time that flips over and the majority of dollars actually flow into go to market all through the growth stage of the company and it’s not really been optimized. If you think about burn, multiples are a very popular topic these days. Efficient growth is a very popular topic. 

John Jahnke
But when capital was free, people were spending $3 for every dollar bar they might generate, which is not sustainable. I think we’ve entered a much healthier version of the world where people are not only thinking about building a great product, they’re thinking about distributing it in a cost efficient way just to visualize. 

Brett
What it looks like if we’re a customer. So let’s just say that we’re an established company, we found product market fit. What’s it look like when we work with the platform? 

John Jahnke
Yeah, so we think about it from a maturity journey standpoint, because we help isvs launch their cloud go to market, and we also help isvs who are already operating their cloud go to market at scale, say tens or hundreds of millions of dollars of throughput evolve that to scale it so we can meet people where they’re at in their journey. And in general, you’d engage with us. It often starts with a listing in the cloud marketplace. So if you went to AWS Marketplace and you search for crowdstrike, you’d find CrowdStrike’s platform listed in AWS Marketplace. And someone could click to buy that Tackle powers the back end of that. So if someone actually clicked to buy it, all the API calls would happen through Tackle, but no one from a buyer perspective would ever know they think they’re just working with Crowdstrike. 

John Jahnke
And then we give tools for different personas inside an ISD. Because this is a multi Persona problem. It oftentimes starts with the partner team who’s thinking about how do I partner with Microsoft or Google or AWS, and then scales with the revenue team? Because as cloud go to market evolves, every rep in every company needs to know how to win with cloud when they’re looking for budget. The cloud budgets are durable and hundreds of billions of dollars in size, they’re really easy to access. So sellers need to know how to take advantage of that. 

John Jahnke
So we support personas like alliances, like Rev Ops, like finance, like salespeople, and they all have slightly different experiences and we take this whole cloud go to market thing, we manifest it inside of Tackle and we also manifest it inside of Salesforce because for every rep to know how to win with cloud, it has to show up in the tools that they use on a daily basis, which most often is Salesforce. 

Brett
How long did it take you in this journey to really feel like you had reached product market fit? And what did you learn along that journey? 

John Jahnke
Yeah, it’s a great question. I think product market fit evolves and there’s points in time where product market fit happens. We got to ten customers. That was like our first inkling that we had product market fit and were like, okay, how do we go from ten customers to 100 customers? And that path was pretty straight. And then we knew that we’d evolved to be a multichannel ecommerce platform. So enable. We started with AWS and then we enabled Microsoft and Google to follow and that was like a second phase of product market fit. It was really clear our customers wanted that multi channel distribution from what were doing. And now there’s like this third phase of product market fit where the market’s changing. 

John Jahnke
And it’s not just about selling, it’s about how do you engage with cloud provider sellers in order to align around delivering value to a joint buyer. It’s about using data to analyze your pipeline to make decisions about the best opportunities to go on this journey. So I remember I listened tod from Okta was talking about when he felt he really had product market fit and it was much later, he said it was like $30 million for them. And I remember listening to that and being like, wow, that seems much later than I would have thought. But I do think this evolution of product market fit makes that answer probably much more normal. I feel we have very strong product market fit, but I also think it’s very early in this cloud go to market evolution. We’re in the third inning of cloud. 

John Jahnke
We’re in the first out of the first inning of cloud go to market. And digital selling has a long tail. 

Brett
To come when it comes to the market category. Is the market category cloud go to market? Is it digital selling? How do you think about the market category? 

John Jahnke
Yeah, this category thing, because people will always be like, well, Tackle created a new category, this cloud go to market category. And I agree with that and the way I’ve come to learn, and that wasn’t what we set out to do. We set out to solve a problem that would make sense to our customers, that would have them give us money and have us exchange value for that money. We were successful in accomplishing that. But then we learned we created this new category. And I think category creation is about budget. Was there an existing budget for what you were doing, and how do you get access to that? And I think category creators, oftentimes there was no budget. There may not even have been a clear owner. So you’re doing something new in a completely new way. 

John Jahnke
And five years ago, category creation was all the rage. Everyone wanted to be a category creator, when in reality it’s actually really hard. If there’s no budget, things take longer to scale, it takes longer to get people aligned. And I do think we’re in this new category zone, but the category is changing. If we thought about cloud, I would say Tackle is the category creator for cloud go to market. If we evolved to digital selling, I think cloud go to market is a subset of what digital selling is. And even the definition of digital selling is still very fuzzy. 

John Jahnke
I think there’s this next generation tech stack emerging where all software companies will use new tools in order to drive their revenue systems, and those new tools will look like Gong and Clary and Tackle and crossbeam and a variety of these other tools that all map into the digital selling future. 

Brett
From a tactics perspective, what did you do to create that line item and really establish the cloud go to market category? 

John Jahnke
The first thing, it was about execution. We started as the marketplace company, and we helped software companies kind of list and launch their cloud marketplace businesses. And that was where were the first few years. But as the shape of the market changed, we actually had a lot of debate about what was the market like, what was the platform were building and how would it evolve. And we created the term cloud go to market. And we took a step back from the marketplace company. We’re like, there’s something bigger here. And we had to think a lot about the workflow, like, what is the workflow that marketplace was part of, which is the workflow of selling. But what were the steps before marketplacing that had to happen in order to make cloud go to market successful. So the first thing we did was title it. 

John Jahnke
We actually created the name cloud go to market. We defined what cloud go to market was. We started to create content around that concept, and then we had to wait and see, would the industry embrace that? And it was really fascinating to see over the first six months after we started to write content and kind of rebrand the company and our platform. With this cloud go to market term, you started to see others emulate it. The cloud provider started to talk in that way. You started to see people on LinkedIn change their title. And now if you search cloud go to market on LinkedIn, there’s all these people whose titles come up as the cloud go to market person. So those were some of the things we did to start to make it clear that this was a new zone. 

John Jahnke
And just creating a name and getting people to rally around a name organically was the biggest thing for us. 

Brett
This show is brought to you by Front Lines Media, a podcast production studio that helps B2B founders launch, manage, and grow their own podcast. Now, if you’re a Founder, you may be thinking, I don’t have time to host a podcast. I’ve got a company to build. Well, that’s exactly what we’ve built our service to do. You show up and host, and we handle literally everything else. To set up a call to discuss launching your own podcast, visit frontlines.io podcast. Now back today’s episode. I did an interview a few months ago with Godard, the CEO and Co-Founder of G two, and I asked him, what’s your number one piece of advice for a company that’s creating a new category? 

Brett
And he said, partner with your competitors, go and work closely with your competitors, get them together, or get all of you guys together and really champion the idea and the need for this new category. I know you mentioned there, you’re seeing others are starting to use the term, how does that feel when others start to use your term? Do you ever have moments where you think, hey, that’s ours, or are you just very clear headed and thinking, no, that’s truly better for us if everyone starts talking about this? 

John Jahnke
Yeah, I mean, I think imitation, size, form a flattery, and it takes an ecosystem approach like digital selling is a really big and complicated thing, and cloud go to market is actually a pretty big and complicated thing. It’s not a solution that will be driven by any one person. So I’m in no way I’m excited when people use cloud go to market as a term because I believe deeply that this will become a default substrate of every software company selling system. And for that to happen, that’s a thing. Hopefully Tackle plays a really big part in it, but it’s much bigger than just Tackle. 

Brett
You take us back to those early conversations and early meetings when you were debating this idea of, should we create a new category? Should we sell into an existing category? From my conversations with founders, that’s always heavily debated. As you said, creating a new category is very difficult. That’s the sexy path, but it’s also not the easy path. So what were some of those early meetings like as you were having these discussions and what led to you making that call of, okay, it’s going to be hard, but we’re going down this way? 

John Jahnke
Yeah, we thought a lot about the personas and the budget. Like where were the dollars coming from and what were the personas that we’d focus on as this market evolved and in the early days and I’d even say like this is a multi Persona problem, but I would reflect back on Salesforce. You think about the early days of Salesforce. It was the vp of sales who was buying Salesforce. In the early days, rev ops or sales operations didn’t even maybe exist or didn’t have those titles. So there was no budget owner for Salesforce that looked like that. And I think over, like the budget owner for Tackle does become rev Ops, but there’s always going to be a business sponsor behind it. But we’re so far away from that. 

John Jahnke
And the more we debated that, we’re like when we see rev Ops start to become a clear decision maker in cloud go to market, that’s when this market’s maturing in a new way. But up until that point we’re still in this category creation zone. So we have to go forth and build the success, build the momentum and partnership with our customers and partnership with the clouds in order to get to that point. 

Brett
What Playbook were you following when you followed this category design process? Was it the play bigger playbook where you map out a pov and you have lightning strikes and all of that, or what was the playbook that you were running? 

John Jahnke
I wish I could say we did. I know our head of marketing was a play bigger person. I wish I could say we had an absolute playbook. I think the playbook we run as a company is it starts with our customer. So we really just tried to focus on how do we deliver value to our customers today? What value do they want from us in the future? How do we go build that and get that in their hands so they get to the outcome that matters? I don’t think we had this step by step, perfectly laid out approach to build a category, but there definitely were some external influencers along the way. 

Brett
Early on, did you have any customer conversations where they just didn’t get it? They saw cloud go to market and they’re like, john, what the hell is this? What are you trying to sell me? 

John Jahnke
Yeah, totally. It’s funny, we had a ton of inbound as a business for a lot of years, and most of that inbound came from people who understood exactly what were doing, had heard about us from one of our customers or from a cloud provider, and was like, yeah, I believe cloud is part of my system go to market system. In the future, I don’t want to build that. I’m going to go partner with Tackle. And that inbound was great for years. But as we started to build out our salesforce, we tried to say we need to control our destiny. We need to very clearly define our ICP, and we’re going to think about enterprise software companies as our ICP. 

John Jahnke
And how do we hire salespeople to go out and spend time with those enterprise isvs, educating them on the power of cloud go to market. That was when you realized it was early from a category standpoint, could we send salespeople to go talk to you, name your big 40 year old vintage ISV, and they’d be like, I have no idea what you’re talking about. We sell through distribution and channel. This cloud thing is not a real thing. No one’s going to buy our product, bottoms up from the marketplace, what’s a private offer? And we had to ultimately get to the point where we had to focus on those who got it. We couldn’t actually go convince those people that this new go to market system needed to be part of their system. 

John Jahnke
And when we did, oftentimes they would fail because they would treat it like an experiment. But the people who got it looked at it as this is a longer term, enduring component of our go to market system and we’re going to invest in it accordingly. So the market’s changing. I’m a huge fan of Jeffrey Moore and crossing the chasm, and we’re in that early, majority phase of the journey where people we talked to three years ago who are like, no, our customers would never buy that way, are coming back around and saying, yeah, we think cloud go to market is something we need to do. 

Brett
How did you go about launching the category name? Did you do it all at once? Were you formally announced it, update the website? Or was it more of a kind of slow rollout as you introduced this concept into the market? 

John Jahnke
It was a slow rollout. We started with content and just started to socialize the concept in content. I’m a huge experimenter. I spend a lot of time with customers and partners, and so I experiment with messages. Sometimes this frustrates my team because sometimes I’m not exactly on script, but I like to be the abstract, smart, creative. So we started to experiment with it, and then we got to the point where we did an event, and it was a larger virtual event during the pandemic. And we called that event cloud go to market experience. And we ended up working with the cloud providers. They sponsored that event, and that was like the launch event for cloud go to market. And from there, we started to see the adoption of the name across the industry. 

Brett
Based on everything you’ve learned so far from creating a category, what would be the number one piece of advice to a Founder who’s looking to do the same? 

John Jahnke
I mean, I think deeply about if you want to create a category, like, does what you’re doing justify a new category? And do you understand that sometimes creating a new category actually takes a lot longer than you think it might? And I think every time I get into these debates, the creation of the new category is validation that your customers are getting value from the platform you’ve built, the product they’re using, and the fair exchange of dollars they have with you to accomplish that. That’s all that really matters. If you deliver value to your customers, and customers are willingly working with you to get the outcome that you provide, that’s when you can think about, okay, I’m creating a category around something meaningful. If you don’t have real usage, if you don’t have real traction. 

John Jahnke
Trying to create a category, I think is a bit of a fool’s errand. 

Brett
What role have analysts played in your category creation efforts? 

John Jahnke
That’s funny. When we started, there were no analysts covering what we did, and we actually created. So Bessemer did our series A, and Bessemer does this state of cloud report, I don’t know if you’ve ever seen it. And prior to Tackle it was one of the best pieces of cloud research I’d read every year. And when we started to gain some momentum, as the marketplace people, customers would say, hey, do you have any analyst data? Can you talk to us about what the GMV looks like through this? How big is this movement going to be? And there was nothing. And so we’re like, well, why don’t we go create something? So we created a state of the cloud go to market. 

John Jahnke
It was originally State of cloud Marketplace report about four years ago, and we did a whole bunch of research across the industry and then published, effectively, analyst report. And that was the time that report started to get attention from some of the analysts. And we started to get inbounds from Gartner and Forrester, where they’re like, hey, we saw your report, really curious about what you’re doing. Can we start a conversation? And then that started to trigger some analyst engagement. We don’t pay any analysts still, and that’s maybe something as we continue to get bigger, we’ll think more about. But now actually there are analysts paying attention to this market. The cloud provider sponsor analyst reports relative to cloud go to market, and you’re seeing a lot more attention to it. 

Brett
When it comes to the category creation strategy for the next, let’s say, twelve months, what are the top priorities? What are you focused on achieving? 

John Jahnke
For us, we created cloud go to market as a concept, and then we had to evolve our platform to meet the requirements were defining for cloud go to market. And that was combining the cloud marketplaces with the Cosell process and using data to inform how this system would work, manifesting that experience inside of Tackle and inside of Salesforce. So for us, getting to feature complete across that cloud go to market platform vision is the primary priority. And with that, as we get to feature completion, we need to get product adoption across our customer base, across that entire spectrum of what the platform takes. I think cloud go to market is here to stay. And now it’s about driving success with our customers across this new evolved space versus where they were maybe a year or two ago. Very focused on marketplaces. 

Brett
As I mentioned there in the intro, you’ve raised over 148,000,000 to date. And it’s from some of the biggest names that exist in ventures. You have code two, Bessemer, a 16 z, all the big names that every Founder would dream of working with. What have you learned about fundraising throughout this journey? 

John Jahnke
Yeah, it is so much. And people are always like, oh, how did you get Andreessen to invest? Or how did you get Bessmer to invest? And it really comes down to customers, the traction you have with customers and ARR and investors called. I would get calls from my customers that investors were reaching out to them long before investors ever reached out to me, which was really interesting. And one of our investors talked to 30 of our customers before they ever talked to me, which I thought was unbelievable. So I think coming back to what’s the thing you really need to focus on, you need to focus on your customer delivering value. I think the second part of the fundraising journey, the early dollars, are absolutely the hardest dollars you will ever have to raise. 

John Jahnke
If you get to an a and you have real customers, real traction, real ARR growth, raising money becomes much easier. Getting to a seed round when you maybe don’t have any customers or have a tiny bit of customer traction is incredibly difficult. And I think it’s important just to go into that phase of your lifecycle knowing that’s going to be really hard. But if you can nail it from a customer attraction standpoint, then the dollar should come easier. And I think the last thing, raising money is all about storytelling. And your ability to tell your story, translate that story to people in a way that makes sense and gets them excited, makes it clear that you’re an expert and you’re passionate about it, and you’re going to run through whatever wall you face in order to get to the outcome you believe in. 

John Jahnke
And I meet a lot of early stage founders, and I think they underinvest in the story. And I think the story is sometimes the most powerful thing you have to think about when you’re raising money. 

Brett
Are you a naturally gifted storyteller or is that a skill that you had to really nurture and develop? 

John Jahnke
Maybe there was some of it in there just naturally, but being an se, and this goes back to that early career journey when you work for a technical company and you’re trying to help people who don’t understand what you do solve complicated problems, storytelling becomes a bit of a crutch because you have to translate really complicated things into things people understand. And I spent so much time doing that for nearly ten years. And oftentimes in emerging tech, where it wasn’t only people didn’t understand what were trying to help them with, they didn’t even understand the problem were trying to solve. So I think I’ve had a lot of practice telling stories and trying to tell complicated stories. And I like the test of trying to get people to understand. How can you make anyone understand what you’re trying to accomplish? 

Brett
One thing I’ve seen firsthand in a lot of tech companies and startups is that the Founder can have the story dialed in very clear, very compelling. But when it comes to getting alignment and everyone on the team sharing that story, being able to communicate that story, it’s a struggle. Has that been a challenge you faced? And if so, what did you do to get the team really aligned around that story? 

John Jahnke
Yeah, so when I worked at Green Plum, Scott Yarrow, he’s the Founder or one of the co-founders at Green Plum, and he was a really amazing marketer and amazing. He actually, were struggling with that exact phenomenon, and he’s like, hey, we’re going to certify every single person in the company on the five minute story. And we actually went through a process where we created a five minute story. We created a deck. Every single person, whether they were in finance or in people or in sales or in engineering, had to be able to tell that story. And it really helped galvanize the system around it. We haven’t done that at Tackle, but it’s something we do. Try to promote the story internally, get people to hear it as often as possible, and then they need to make it their own. 

John Jahnke
Everybody needs, especially your customer facing people. We always had this problem in the early days. I knew every customer’s story. I could go through our first 50 customers and tell you how they were using the product, why they were using the product, the success they had, who the person was in the company, why they bought it from us. And you hire salespeople and they hear you tell that story, but it’s not their own. So even once you get people on message, you have to help them make the message their own by getting them to live it with people to the point of success. That’s when I think you can be really successful translating that story. 

Brett
One thing that I see a lot in the media and social media is that entrepreneurship and being a tech Founder gets very glamorized, and it looks very cool, looks like a very sexy thing to go do. But as I’m sure you’ve experienced, it’s hard. There’s a lot of challenging moments. What’s been the most challenging moment for you, and how do you navigate that moment? 

John Jahnke
Yeah, I think my three most challenging moments in this role all happened this year, and the first one. So we, like many software companies, embarked on a restructure early this year. And I think the market was changing, and it was unclear to us how much the market was changing. And we came to the conclusion that we had to do a restructure. And it’s a really kind of terrible conclusion to get to, but to keep moving forward and to help our customers, we had to kind of redesign the system. And at that time, I got a lot of advice where everyone’s like, hey, you have to go deeper than you ever think when this happens, and just make sure you think deeply about that. 

John Jahnke
And we thought we did, and we executed on a restructure, only to figure out a couple of months later, we made a mistake and didn’t do it right. And we ended up doing a second one, which was really hard. Like, the whole thing was hard. But that mistake is one of those mistakes I’ll look back on forever and be like, I wish we could take it back. I wish we could have thought more deeply about it up front and only had to go through it once instead of having to go through it twice. Because the first time, I think people understand. The second time you lose a lot of trust, and you lose trust the first time, too. But that was a really hard time. 

John Jahnke
And I think similarly, as went through this peacetime, everyone was growing, everything was up into the right capital, was nearly free to a pretty wartime environment. And it takes such different skills to operate in this wartime mode. And there’s a lot published about wartime ceos and wartime leadership. And when you go through that, you realize that not all leaders are set up to be wartime leaders. And that challenged us to think deeply about transforming the leadership team. And again, repeat founders tell you this, they’re like, you will go through this. You’ll probably go through it repeatedly if you’re scaling and being really successful, because a lot of people just don’t have the experience to go from zero to 100 or zero to a billion. That doesn’t really exist, and you have to transform the leadership team. 

John Jahnke
So that was the second thing, because these are people we built the company with, these are friends, these are people I love spending time with that. Ultimately, we had to conclude that everything they did was amazing for us, and we valued that deeply, but we needed something different for the next phase of the journey. So that was probably the second low point for me, just navigating that. I feel like I’m probably a better CEO now for having lived it. The last one was the SVB event. Probably an incredibly stressful weekend for so many in tech who worked with them and talk about all those other things were in our control. We made mistakes. The market changed. The market was out of our control, but we made mistakes. We had to deal with our mistakes. SVB was totally out of our control. 

John Jahnke
And there’s nothing more terrifying than thinking about your company going away based upon something that you couldn’t control. That was another really hard lesson, and one I don’t look forward to living through again. 

Brett
Yeah, hopefully we never have to live through that again. I remember all of that unfolding and just the roller coaster on my end of thinking, okay, we don’t bank there, so we’re okay. And then the realization that every one of our clients banks there, and if they lose all their money, we’re basically screwed. So that was a very intense weekend. And I remember when the news came out on Sunday that they were going to backstop the bank. A big sigh of relief. So everyone in text felt that I. 

John Jahnke
Know exactly where I was sitting when that news broke and I got a text from one of my investors saying this was coming. And then it came out right after. And sigh of relief was I didn’t even know how stressed I was and it was stressful and I knew I was stressed. But until that wave of relief came across, I didn’t really realize how crazy that period was. 

Brett
That has to be the case for anyone who’s in tech or any tech founders who had exposure to that. They’ll remember for the rest of their lives where they were the moment they got the news that everything was going to be okay. 

John Jahnke
Yeah, definitely. 

Brett
I appreciate you being very open as well and answering that question. A lot of times I ask that and I get kind of like fluffy answers of, oh, the hardest decision was trying to decide which term sheet do we take from these two different tier one investors. And it was just, I couldn’t sleep because I just couldn’t decide. So appreciate you being very real and very open. And I think those are the types of stories that founders really love to hear. So again, really appreciate that. 

John Jahnke
Yeah, the road to 100 million is not a straight line. That is for sure. 

Brett
Yeah, it’s one of the things I like about doing this podcast is you get to really see behind the scenes of companies that are growing. They’re doing amazing things, but you get to see behind the scenes that it’s really hard. It’s not easy, and there’s ups and downs along the journey. And I think it’s very important for founders just to know that there are going to be highs, but there’s also going to be a lot of lows as well. Just how things work. 

John Jahnke
Yeah. And you can’t overreact to either of them. When things are good, you have to underreact to them. When things are bad, you have to underreact to them. Especially as a CEO, I always try to think like, steady hands on the wheel. That’s what we need. If I’m jerking the wheel left and right, it’s really hard for everyone in the car to stay in place because it’s not only like the highs and lows of the year or the quarter of the month. Sometimes it’s a day. It’s like call by call. You could have an amazing call. Earlier this week, I had an amazing customer call followed by a terrible customer call. And I was like, man, these two things could not be like, they’re completely opposed and you just have to keep working. 

Brett
Have you ever seen that chart and it’s like a year in the life of an entrepreneur, and it’s like a squiggly line. It’s like, I’m rich, I’m bankrupt, I’m rich, I’m bankrupt. That’s how I feel like my day is. It’s like the ups and downs, it never ends. It’s not over a course of a year. That’s a daily occurrence. And I think that’s the case for most founders. It’s ups and downs all day long. 

John Jahnke
Yeah, totally. 

Brett
We are up on time here, so I want to be respectful of that and just end with one final question. Let’s talk about the future. So if we look at the big picture vision here, what’s that going to look like over the next three to five years? 

John Jahnke
Yeah, I think I said this before. Nailing the cloud go to market platform is our primary mission short term, like I’d say over the next 18 months. And we’ll continue to invest heavily and innovate greatly on behalf of all of our software company customers who are looking to scale this as part of their business. From a longer term standpoint, I think there’s really two things. One, I think about this as there’s $755,000,000,000 of b, two, b software sold, and some of that is migrating to the clouds. Will that be 10%? Will that be 50%? We’re not sure yet. We think ten to 20% is extremely reasonable. And how can we help that ten to 20% accelerate its migration to the cloud? So we think about ways to innovate to make that happen. 

John Jahnke
Partnering the cloud marketplaces, or cloud go to market with channels is a big area of investment right now because we think that helps accelerate that migration of software to the cloud on a longer term basis. I come back to selling software is the most expensive part of every software company and has really yet to be disrupted. And there’s all these signals of change. There’s product led growth, there’s usage based pricing, there’s cloud marketplaces, there’s ecosystem growth, there’s all these signals that things are changing. But we’re still in the earliest days of that digital selling revolution. So I look forward to continuing to invest in how to make selling software as efficient as possible for all of our customers. 

Brett
Amazing. I love the vision and I’ve really loved this conversation and would love to keep you on and keep asking questions, but we’ll have to save that for a part two perhaps in maybe a year from now. John, before we wrap up, if there’s any founders listening in that just want to follow along with your journey? Where should they go? 

John Jahnke
Yeah, you follow me on LinkedIn, John Jahnke on LinkedIn or on Twitter. Exact same handle. Or you can always follow tackle.io to see content specific to cloud go to market we publish a lot. We love to publish customer stories early companies who are just starting to scale their go to market systems with cloud up to some of the largest sellers in the world. So we’d love to share what we learned along the way and appreciate it. 

Brett
Amazing. John, thanks so much for taking the time. Really appreciate it. 

John Jahnke
All right, thanks, Brett. 

Brett
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