2024-04-04--t03-06-28pm--guest538371--jeff-wharton
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Jeff: [00:00:00] All right, Jason, thanks so much for joining us today, man. Glad to have you on

Jason: Great to be here, Jeff. Thank you.

Jeff: We've got a whole line of stuff to talk about today. I think you have, one of the more diverse backgrounds of people we've talked to between, working at VC funded companies, PE across different roles engineering PM, there's a lot we want to get into and we'll squeeze into this thing today, but first I always like to just find out, cause I think it informs.

So much of the rest of the conversation, what did the career path look like to get you into PM and then to where you are today? When we came up and went through school, it wasn't like you'd go to school for product management. So how did you wind up taking that path?

Jason: I don't wanna start with my early childhood I think as a kid, . I pulled everything apart that I could get my hands on, and I've always been inquisitive. I even pulled things apart that didn't belong to me. I took my brother's toys and pulled them apart too, and I couldn't put them back together again.

But over time I started to figure out how things worked and then slowly started to fix [00:01:00] things. And so, you know, I always had that kind of inquisitive nature. And that sort of led me to engineering. And I worked for 10 years on mobile phone development and I really enjoyed working on consumer products because I could see where the product was going and over time with new product introduction, spent more and more time with customers because I'm working on products that were being introduced.

And so you see that kind of go to market perspective. And I thought that was really interesting. And got my curiosity on the commercial side. And I think that brought out the desire to get into product management away from being in a cube, just designing something for several months and rarely coming up for oxygen, but actually stepping away from the office and being with customers and out there in, in the industry, seeing where the products went.

And I really liked seeing the whole end to end. So that's really what got me into product management is. After being in engineering and learning, obviously a lot there was this fact that I could now see the end to end, where [00:02:00] it was going, why it was important. And over time, I've led both engineering teams and product teams.

And I think that probably a CPO is probably best suited for my personality style. I'm comfortable with technology. I'm comfortable with business. And I'm probably more of a generalist. I work with some Very bright specialists. And I don't think I am one of those, everyone has to know their lane and I think that I'm a very good generalist.

I'm curious. I have broad interests. I'm still an engineer at heart, but I think that's, what led me to be a product manager and be a CPO.

Jeff: Makes sense. Now I was got to hit on this. If I see it, did I see you had a stint where you even crossed over to the dark side and did a little marketing?

Jason: Yeah, that was more by virtue of the organization. They, we had a marketing team and they needed some leadership and that marketing role was a lot more product marketing than say brand marketing. And there was lead gen and everything like that. So I did lead that, but.

I learned more than I'd led. Let's put it that way.[00:03:00] 

Jeff: Yeah. That's the one thing when you've hit on so many pieces that you have is I feel like it's a great just chance for education, but I think a lot of people would be surprised at how much marketing and product can cross over. I feel like at least here at log rocket, I'm, similarly, my favorite things are talking to customers.

We've had a lot of input on product direction because of all that contact. And, if you can get an org where engineering product marketing sales to are all firing and aware of how product works. I think that's the best combo. So

Jason: Absolutely.

Jeff: that's really cool. Now , any of those points throughout that.

Where you hit on all of that and where you've ended up today. Do you feel like that, either changed the course of your career, any of those roles or any of those kinds of stints in, in any of those things? Or, do you think it more that broad exposure brought you to the point now where you can do some of the things better that you're doing now?

Jason: For sure. The broad exposure helped and it's a happy accident. I didn't plan any of it. Like probably most people in their careers. You have some vague idea [00:04:00] of what you want to do, but it's more function of what gets put in front of you. and the environment that you're in, the opportunities that come up.

And so it was a lot of happy accidents along the way. But yeah, having the broad scope of roles and exposure. Of course, I lived in Asia and in Europe and the U. S. I've lived in different regions. And so I have a good appreciation for the needs of different markets as well, and an empathy and understanding that customers needs vary.

So I think having that diverse background helped me to , , really think about the customer experience and the whole end to end, and so as a CPO if I'm good at the role, it's because I have empathy for other parts of the organization and the challenges they face, I don't just have a myopic view of well, I'm in product management or, I'm running development and this is what I believe.

And, that's the only truth. It's not, you have to take into consideration the impact that your decisions are making across an organization for it to be [00:05:00] effective.

Jeff: And that can go back all the way to, even considering the impact when you're doing something like taking apart your brother's toy. Right. I feel like there's so many people I've run into who trace their curiosity or, who showed this kind of curiosity and have this multiple.

Point exposure and invariably when you go back far enough in their life, they talk about, I just took all this stuff apart when I was a child and, phones. And I've, I have fond memories of taking apart all sorts of things that turned out my dad really needed. And then you got to deal with the user impact on how do you deal with that?

So that's empathy. That's a user impact all rolled into one at a

Back a little bit more to now, though, and on a more serious note it's interesting that you have this kind of background between engineering and PM, because I feel like we see so many organizations where that's a critical pathway that can fall down. How have you, seen and run into kind of this conflict?

And how do you [00:06:00] mediate the, maybe differences of opinion or differences of. Alignment there. And how do you make sure that both those teams are rolling up? And I guess to compound that, do you think having those teams report into the same person is helpful?

Jason: Yeah, it's always an interesting discussion and I have people ask me that a lot within the organization, right? So just to be clear, I have worked in organizations where I've been a CPO and had a CTO counterpart. So peer level, I've reported to a CTO in some companies, and I've had a CTO report to me in others.

So I've had everything. So I think I can say from my experience that I do see the difference. Now let's just go back to the CEO. The CEO is the one that cares about the structure of the organization predominantly, right? And most CEOs. have said to me, they want some healthy tension between product management and engineering teams.

And I understand that. And I don't discourage healthy debate. And so the thing is, I want to ensure that if I'm running both [00:07:00] product management engineering, I need to have healthy debate, but it needs to be data driven, not power driven. And sometimes if you have the wrong team structure, it becomes a power play.

And so that means I've got to change the leadership because that doesn't work. So it does take the right type of people to make that sort of work. If I'm going to be a CPO I have to have a collaborative team that's on the technology side. If the technology side that's that engineering is reporting to me. So I have VPs that like currently I have VPs of product management and VPs of engineering reporting to me. And I don't have favorites. Okay. And I think that's the important thing is you just have to be pragmatic. I take my cues from a company strategy and are agreed upon, key initiatives.

But I have seen also that when I joined a company, I had to prove myself because generally speaking engineers want to report to engineers. Product managers want to report to product managers. They want to port report to an expert in their field. And so if A CTO is now reporting to A [00:08:00] CPO, they're gonna be like hang on a second.

What am I gonna learn from this guy? Does this guy know what my, what I have to do? So you have to earn the respect, but ultimately, we all re report to somebody who is not an expert in our field, unless you're CEO. Is a technologist, but then the CEO reports to the board and you can't assume that the board is either.

At some point you're reporting to someone who has Broader experience and maybe not your experience. And so I think at a leadership level, people just have to get over themselves and realize that, you can't always report to an engineer. You can't always work to report to a product manager or someone with that background, but you do want to work with someone, work for somebody who has an appreciation and is unbiased.

And I know that's not easy to do, that's obviously something I strive for. And that's why I say I don't have favorites. I try to be pragmatic. I look at what is it doing for our business?

Jeff: you bring up, I think a couple really interesting points. One of which is right. I feel like throughout career, people want to report to someone who is an expert in their field and want to [00:09:00] learn from them and what I've realized is you hit a, Certain seniority point and what you're learning is probably no longer expertise in your specific field, right?

If you're a CTO you're going to be the most senior technologist in the company. Even if, maybe like you said, maybe the CEO is a technologist, maybe not, but what I've realized is, there's a good opportunity to, you hit a certain level of leadership and it's just about people. It's a people game at that point.

And you start to learn, hopefully, how do you better, organize, how do you better align? and that's what I've, I think over time I've learned and been able to look to those people who I report to when they're not experts in my field, where I can still gain a ton from that.

So that's. That's always possible. 

Jason: My current CEO, his whole career has been in enterprise sales and I'm learning so much from him. It's fantastic. And yeah, I agree a hundred percent. And I think everyone has to approach their work that way. You want to learn from everybody around you.

Jeff: yeah, I always, I tell people on my team, pretty much, and I counsel people outside of [00:10:00] that. When you're in a role, think about what you're learning. If you stop learning,, take a hard look and see, is it something you're doing or if not, look how you can change what you're doing to do that.

Or maybe it's time to start looking for something else. Cause you always want to be learning back to the, you talked about healthy tension. That's always, I think an important point, is you want. Too much Kumbaya and you probably aren't progressing enough, but too much, you also don't want fiefdoms.

You don't want people creating their own little pockets of power. So how do you kind of balance that, right? How do you look at, you want to create tension. You want to create people ensuring that they're giving critical feedback and pushing on each other so that you elevate the whole thing. But at the same time, you want to keep it from, turning into just little spits and spats and power grabs.

How do you balance those two dynamics.

Jason: I think there's a number of things to it. I don't think there's any one answer, but a few of the things that I focus on is allowing each team to focus on their swim lane, what their strength is. Simple level product management, they focus on the what, and engineering focused on the how.

And so I encourage product management, please [00:11:00] don't tell engineering how to do things. And I go to engineering and I say, please don't tell product management what it is we need. Now it's okay to have a discussion, all right, about it. But at the end of the day, please recognize each other for the, your expertise. And a lot of it comes down to personality types. 80 percent of much of what we do every day is just a function of our personalities. And 20 percent I would say is, your skill set, right? And so that 80 percent I think is really important and you've got to build a really good team.

And I've had to make changes in team structure to make sure I get the right dynamic. I agree with you. You don't want the come, come by our moment where everyone's just, you got a bunch of yes men. But then, you also don't want to have people that are continually arguing and have this power play.

So first you've got to have the right team, and then you've got to set the ground rules of how you engage. And that's respecting each other's job and role and allowing them to own that. And totally fine to make recommendations. But at the end of the day [00:12:00] that group gets to make that decision. Engineering gets to decide how they get to decide what the technology architecture is and I'll challenge them as a leader, but you've got to empower people, hire the right people, hire people better than you and empower them to go do great stuff and then. The people around them will respect that and I found that the case, if you hire the right people, have the great teams, then, product management are not going to debate as much with engineering because they have confidence in them.

Wow, these guys are good and vice versa.

Jeff: no, I think that's so key is right. You set a place for the discussion. I think the way we've approached this is similar, right? You have the discussion, you have that debate, you set out though, who's ultimately making the decision versus who's an advisor. And the last piece I've run into that I think has been important has been also, we can argue and debate and do all of that and, have it out passionately here.

But the point I've always made to the teams is, When we leave this room now, we came to a decision and we're all on that page now. So that's what we're doing, whether or not you were advising against it, [00:13:00] once we leave the room, this is the plan we're all doing it we're bought in and it's game on a time to align and all row together now.

Jason: That's a great point. I agree with that a hundred percent. Yeah 

Jeff: so that brings us to, where you are today. So you're at a company called Simpro. And I think this is a great opportunity to maybe talk a little bit about how does this theory turn into reality on the ground? Cause you were brought in, fairly recently basically to, to consolidate three distinct businesses and products.

And so you don't just have an engineering team and a product team necessarily, it was probably, maybe even more than one of each and, it's a pretty big job. Can you give us a little background, for first of all, just on. The situation. And then how do you come in and approach something like that?

Jason: so private equity firm that I work for, K1 Investments, they bought three companies that are in the same industry. They're in the field service management industry. And for the first two years of operation, they just let them run them themselves and did no integration. And so when I joined.

As the CPO with the plan [00:14:00] to consolidate there was three different engineering teams, three different product management teams, and the products themselves are completely monolithic. There's no way to integrate them from a technology perspective. But they're serving like a similar industry.

So it's complicated, right? They overlap in some areas, they compete in some areas, they're complementary in some areas, disparate in a few, and they're in different regions of the globe where they're, successful. So it couldn't get more complicated. Really? And the reason that it wasn't solved before I got there is because it's a complex problem to solve.

Usually if it's an easy problem, people go figure it out. Here I am. So I think the process for me is first looking at, you've got to start with the customer. You've got to be clear about who your customer is and what you can do for them. And step one was really detailing out the ideal customer profile, the ICP, and looking at the power of the brand of each of these businesses in each region.

Europe Australia, New Zealand, and the U S that's where these businesses are. And they have different strengths in different regions. [00:15:00] And then you've got to look for areas of integration, even at the highest level, that makes sense from a customer use case and the customer journey perspective.

So it really all starts with the customer. And at the end of the day, if you can't find areas to consolidate, then don't. So after I've been at the company now about seven, eight months and I don't think we can integrate these companies these products deeply. I think that they are better to stand alone.

However, we need to talk about the customer experience and the journey of why One customer might need one more than the other and at what point. I don't think the reason it wasn't solved three, two years ago is because it is a complex problem to solve. And so you just have to say look, it doesn't make sense from a customer perspective to integrate them all that deeply.

So they're going to play nicely together and we just map it out for a customer about what, where the value is and why they would want each one. And then you focus on branding to make it look like at least these. These products are similar from the same company. And so there's all that, the apps will need a refresh on the branding and the color [00:16:00] treatments and all that kind of thing.

You want to look like one company. But they compete in some areas and they're a better fit for some customers than others. So there's not much more you can do about that and you just let them run standalone.

Jeff: Yeah, no, that makes total sense. And it's funny, I had looked into what all these products were in the geos and all that. And I was really curious how this answer was going to go because it looked like you had quite the not to untangle there to figure out how to consolidate that.

So I was hoping for, Some clarity here and it sounds like you said it's complicated now do you think part of what for context a couple weeks ago we had on a woman named carla fisk who's a vp of product a company called tebra and she talked about again Post merger bringing products together this kind of exact idea And the thing she had brought, we kind of came to was this idea of, internally you have a lot of people at this point who, maybe have a favorite baby and how do you approach the problem from a baby neutral point of view?

And do you think [00:17:00] that fueled why K1 brought you in here is if someone internal had said, nah, they're all unique products, we need to keep them separate, people might. Push a little bit back on, ah, it's just implicit bias you had from how you came into this versus an external view, you can say, no, it, they really are different and need to be separate.

Does that, do you think that carries more weight in this case or

Jason: Yeah, I think, the fact that I'm a new person to this company and I don't have a bias, none of them are my babies. There's no sacred cows here, right? And so I don't have that same emotional connection to an outcome. And that enabled me to be more data driven. I relied as much as possible on that objective data.

And so we, we try to pull in as much as possible. And then when you show people, good people, the data, everyone will come to much the same conclusion because it speaks for itself. We do an ICP, an ideal customer profile. And we all debated and at the end of the day, it stands on its for itself.

And then we're like, yeah, this makes sense. And [00:18:00] okay. So our decisions are gonna be based on this and this is the outcome. And everyone's yeah, that makes sense. How can you disagree? So you got to pull the right data together. And pulling together an ICP means you going back through the history of all your sales and looking at the types of customers you have and in which segments and where you churn, where's, you know, all that kind of stuff.

And so everything has to be data driven. And I think it has helped me being an outside not coming up from one of those teams so I can provide a bit of an objective for you.

Jeff: I think the other point to hit on here is something that maybe was easy to gloss over. But one of those things, I don't know how many people have exposure to both sides is you've seen companies, , that are operating under PE funding. You've seen companies operating under VC funding.

And unless you've operated in both, I think it's easy to. Not understand that it's a different job. Especially as an executive at, a VC focused company versus a PE funded company. What does that meant over your career? Like, how have you seen that [00:19:00] employ different strategies or what does that mean differently for how you approach your job?

Jason: I'm not sure if everybody goes through the same cycle as I did, of course, but I, when I was younger, I'm not saying I'm really old, but when I was younger, I I wanted to work in startups, that was the place to work. And it, I think everybody has that sort of curiosity. What's, what would it like to be at something that's small and grow up big and it's very dynamic.

And so I had that wanderlust around that too to work for a VC. And it is a very different experience. In a VC environment, You're really focusing on this top line growth. It could be revenue, but mostly it's about number of customers. Just grow that customer base at all costs, right?

Create value in the number of eyeballs that you have on your product or whatever it is. Right. And at some point we'll convert that to revenue. That's the thesis. Just get as many customers you can and somehow we'll figure out how to make money from it. And there's less focus on profitability.

And in that kind of environment, the highs are really high and the lows are really low. The highs are high when you land these big deals, open new [00:20:00] channels and the lows are low. When you start to run out of money. It's like being on a runway and you're trying to take off and you see the end of that runway coming, am I going to just crash and burn at the end of this runway or what?

And then with these different rounds of funding and there can be layoffs and then you're hiring again where more cash comes in. So it's a volatile hype paced exciting journey. And I learned a lot from that. And it's still from a product perspective, it's all about meeting customer needs.

It's a priority and everything, but sometimes it feels like it's a bit scrappy. It can be a little bit half baked because you're just moving as fast as you can. And sometimes you push stuff out the door and it's not quite ready. And that's, talking about MVP, which is a word that You know none of us like to use much anymore, but back in the day, that was the thing like at a VCs, like just to get the minimal viable product out the door and it'll be fine.

When you go into the PE world, it's different. It does a lot more focus on growth still, but it's an emphasis on profitability. And you [00:21:00] get to profitability through product margins, efficiency across the entire business. And a revenue driven roadmap and you focusing on churn, you take care of existing customers as well as bringing in new ones.

And I actually prefer the P world because I think it's more pragmatic and focused on the health of a business and the quality of it for the longterm, but there's still an investment thesis behind it with private equity, right? And so I joined K1 investments portfolio two years in. They don't plan to hold these businesses for 10 years, is it one more year?

Is it two or three? I don't really know. There's a saying in the P world that the companies aren't sold that they're bought. You don't really decide when somebody is going to want to come along and buy you But if you keep doing the right things with a business that's healthy.

So just continue to write, make the right decisions. And hopefully that those timelines will align.

Jeff: I've worked at across both as well. And it was interesting seeing I feel like PE. Companies tend to have [00:22:00] a bit more rubric to them, a bit more organization. Like you said there's a thesis a bit more on how does a business like this work? What does the structure look like?

And they know, you need to have this percentage here and this percentage here. And maybe it's not as much about a seat of your pants, but it can be a really interesting, really educational. Time. And that's interesting to hear. I feel like that's something that people don't often think about enough is what is the cap structure where, where does the capital for your company come from and how that can impact.

what you're doing as well. 

Jason: It does change the way you make decisions about products for 

Jeff: yeah. And then you brought the one thing in there that I think we glossed over that I want to make sure we hit back on. Cause it's, I won't call it a full soap box for me, but maybe a half a soap box is the idea of MVPs. This is something that never sat to right with me, even back when it was really in vogue was this idea of just the minimum, or I think rather people misunderstood In my opinion, at least, that's just me, but what minimum viable meant, you kick out something gross and, cruddy and you put it out in the market and sure, [00:23:00] like minimum viable in that it does the minimum thing you want.

But there's so much more to product experience than that. There's so much more to testing. Does this approach work? As we know now, like UI matters, , how polished it looks. If you put out something that looks like garbage, whether or not it does the function well, people are going to look at that and think, Oh, this is cruddy or this is really good.

How have you, you thought through this? I think you made the point once if you download an iPhone app and it looks clunky, you're going to assume like maybe they didn't invest that much in it. But I feel like this is an area you can get a lot of false positives or false negatives if you're not careful.

Jason: Yeah, I think my attention span is probably measured TikTok video. You know, it's three seconds.

Jeff: Yeah.

Jason: And I can be that way with apps as well. If I don't get driven to the heart of an experience with an app quickly, then I lose interest. Because to me, then I'm like, this wasn't well thought through. And I don't want to use it. And there are so many choices out there. You'll just stop [00:24:00] using that one and go look for another one.

And so I think as as a user I'm impatient and I think a lot of people are impatient. We've become impatient with technology. And so when we're developing products, , we have to keep that in mind. And I've been burnt too many times by shipping a product that was half baked. It never worked out well, it never worked out well, but the pressures of a business can force that sometimes, and you have to fight to resist it knowing what that outcome is going to be. So I've led UX teams at a number of companies but I don't claim to be a UX expert but I do focus on user research. I've always made sure that we've had teams that actually do research. It's not just design. And so you're looking at how the products are being used.

And so you want to get people to that heart of the experience very quickly to solve the problems that they want to solve. So that's, I think, key. And This whole concept of a minimal viable product. Yeah. Who wants to say minimal anymore? People wanna say no. It's awesome and it does [00:25:00] exactly what I want it to do and it does it right Better, to better to have an app that does three things really well than 10 things that it does half baked, obviously.

I think that's probably the focus is to, gotta have the quality and if necessary, reduce the scope and focus on that experience.

Jeff: One of our kind of internal operating tenets, is this idea of focus. And when I always boil that down to my team as is I don't want to half ass anything. Cause when you do that you risk false data, you risk operating under, untruths. So I tell them I want a whole ass on everything which crass or not I think it's the point across, but also there's this concept of how do you iterate?

And for us, I remember for instance, when we started doing podcasts three, I think three or four years ago at this point a minimal viable product on that would be just record a podcast and put it out and see if anyone listens, but you're just going to fail. That's going to get nothing.

Cause people have a mistake in understanding of what a product could be or what is minimal. I feel like the approach is much more test your [00:26:00] core pillar hypotheses that you need something that you need to work in order for the big picture to work. And go forward in that, like for that one, we figured out, can we build a distribution list?

Can we recruit people? Can we record the thing and make it sound good? To your point, can we make it sound professional? And we had a step by step. Process there that only culminated with actually creating a podcast. There was so many core hypotheses we needed to prove that you would never consider any of the minimum viable for a podcast, but it got us here.

I feel prioritization and iteration is much more. The thing, and I think that's something you've talked about too, is like an iterative approach versus an MVP approach.

Jason: Yeah, 100%.

Jeff: So that kind of brings us full circle, though, when you look at this idea of how do you build something like that especially you have an engineering team, product team, maybe currently at Simpro you have three of each still You run into this idea of prioritization, right?

And there's just so many methods out there. , you can use rice, you can [00:27:00] use, whatever have you. How do you guys do prioritization or how do you look at this problem?

Jason: We are using rice methodology, at a high level. But that has its limitations. And with everything that you do it would say with prioritization, you're making assumptions. So the real. Talent there is how do you reduce the amount of assumptions that you have? Or if you have assumptions, what's the range, what's the high and low, right?

And, I probably you've seen this and many of the listeners have too, is that if you're doing the rice methodology and you've got some variation, let's say you talk about reach and you say your reach is your existing customer base. And you have one school for that. And you do the ranking and you have something that comes out to be number 13 on the list.

Transcribed and then you realize hang on, my reach should include the customers I don't yet have, but believe I could, they're in my total addressable market or service addressable market. So you include that and all of a sudden it changes the math. [00:28:00] And now it's number three, it's gone from 13 to three just by making one little tweak.

And I see that happen a lot and it's frustrating. And I think if there's that much variation and variability in, in your rice methodology, then, it's like why you even use it? So it can be undone very quickly. And I think assumptions are product managers, worst enemy. And so the only way to get around that is testing your assumptions, talking to customers and other stakeholders, avoiding the hippo in the room, the highest paid person's opinion. told me that once

Jeff: love that. I've never heard that acronym, but I love it now.

Jason: Yeah. So I'm the hippo, right? If I enter a meeting and I got to keep my mouth shut. You've got to test all these assumptions. And sometimes spread your bets a little bit, take some long term and short term risk. When you're prioritizing, you need to set these milestones for review.

So if you say you've got your roadmap and you prioritize a certain way, you've got to be willing to change it. And obviously a roadmap is there to change, but some people feel [00:29:00] like, Oh, it's the roadmap. And now we've communicated this to our customers and to sales. So we have to deliver it.

No you don't. You have to communicate it effectively that what's in the current quarter, yeah that's in progress. And what's in the next quarter that's planned. And what's in the, quarters beyond that is under consideration. And no one likes that, but you say we want to be agile.

We want to change our mind. We if you come up with an opportunity or a market need, we want to be able to address it. So yeah, it's under consideration. That means we might change our mind. Because we're adaptable and isn't that healthy? And creating these sort of milestones for review and being willing to change course and educating the whole company that's how you operate I think is really important.

But going back to, the rice methodology and other maybe, you know, ROI versus impact and things like that. But the problem is you're stacking these assumptions. And so trying to reduce that and focus on being as data driven as possible will help reduce it. And I've come up with, [00:30:00] when you're choosing between two product features and you're like I just don't know which is the right one.

And so you do this whole rice methodology and you just go into so much detail and numbers. And then you find out that, Let's say if it's on a score of 100, one's a 72 and one's a 73, you're like that's strange. They are evenly matched. Sometimes your hunch is accurate. When you do the numbers, they come out to be the same.

You're like that didn't help me with anything. And then sometimes you just got to say the rice methodology just told me that this is difficult and I can't decide. And so then you have to, use your gut judgment or something else to figure that one out.

Jeff: I think my team will confirm that I'm a bit of a stats nerd. And, I think I came up through a world where, you love to prove things with data and have all these numbers. But the thing people miss often is if you have a 5 percent and a 5 percent and a 5 percent and a 5% chance you don't have, just 5 percent risk or you don't have just 20 percent risk.

You have whatever five to the fourth is for us, these things compound in a terrible way. [00:31:00] That's always the thing to be aware of. And that, but I think you brought up another point too, which is you can use all these frameworks, but at some level, and this is um, you know, the CEO of linear was talking about this a little while back at some point, you got to have an opinion, you got to have a vision for where it's going and that might not match exactly with what these formulas say, but that's where some of the most beautiful product is built sometimes.

Right.

And some of the biggest mistakes too.

Jason: know, when you're CPO, you think, oh, I'm the one that has that vision, certainly I have a document that has our vision and all that kind of stuff I get input from other people, as a CPO, I'd like to think that I'm the visionary.

But we've got a company full of visionaries. And so I think you just have to listen to everyone. And yeah, at the end of the day you might have to just make a decision and go with it. And I think the experience obviously plays a lot into that, to the degree of risk and then you hope that you're a good CPO or whatever, and you made the right decision and there's risk, but that's always part of the fun too.

Jeff: I love that. I love that [00:32:00] thought that there, there's a team full of vision there and you can tap all of it. So important. But also, I think brings you to the, another point of how a lot of these plans get made right is, you as a CPO you maybe have a vision or a founder has a vision and there's product managers who.

Know their line and probably have thoughts of where they want to go. Engineers probably who even are, as they're building it, think about that. But there's other teams too, right? We're all familiar. I'm pretty sure with, sales or marketing coming in and saying, we need this feature.

The market is saying this, or I have a customer who says they'll buy if we just build this. And there's gotta be, I think it's important to listen to those things, but also, There's accountability that comes with being listened to, with great power comes great responsibility.

So with input comes comes accountability. And that's something I think you, you've had a cool approach to and an interesting one that I haven't always heard before. About something like signing up sales for a number, if you go and listen to this. So I'm sure I'm butchering it.

So maybe I'll just leave it to you. And how does that work? And how [00:33:00] do you look at that?

Jason: Yeah, I just think if you want to be an advocate for software development or any kind of product development, you say, we put a lot of pressure on these guys, we want them to deliver great stuff on time, on cost, on quality, and please don't be late. This whole thing, right?

It's, we put a lot of pressure on them to go build what we want and for the most part, they do an excellent job. You've got to be careful what you ask for, but they'll, and they'll build it. So what about sales? Let's say they're getting input from the field and they want things. And I don't want to, rag on sales here.

Cause I think the sales is awesome, very difficult job. And I don't think I could do it, but, um, we want to hold them accountable too. So if they're saying they want something and the market needs it, and if they're going to, they say, if you're not, if you hit my number next year, I need this. Okay, great.

We'll go build it but now you're on the hook to deliver it And so I like to have a roadmap that has revenue attached to it that sales have signed up to [00:34:00] So it's not easy to do. Talk about variability, you know But the process is healthy. You sit with sales and say, these are the 20 things that we're looking at doing this year.

Please put revenue next to them and tell me what you think they're going to help you bring in terms of revenue or reduced churn or whatever it is. But some financial metric that and if they say I don't think that this is going to do anything. It's okay let's take that off the list.

And really, or we really want it. But you just told me that you don't think you can bring any revenue from this. So why are we doing it just for kicks, and so it forces these conversations and eventually you have buy in and you have this accountability. Now you get to that point where you've got this.

Matrix of features with milestones and what quarter you want to deliver it. What sort of revenue you expect in this year and next year, because there's a ramp to revenue with everything. And then you go speak to finance and say, Hey, I'd like to start tracking this. As we launched this add on, obviously [00:35:00] has to be something.

It's not like just a feature. It has to be something more tangible. , we're going to launch this add on. I'd like you to track it separately financially. And I want to report to sales. Every month on how that's going because They wanted this, we built it, and they said they were going to sell it.

So let's measure success. And so you can do that. And I've done it. Problem is, when you do this, that, um, sales miss their targets. Sales miss it. And it's sometimes it's like a muscle. If they're not used to using it, it takes them a while. So the first year of doing this doesn't work well, but the second year of doing it works really well because then they understand the gravity of the decisions they're making.

That if I'm deciding that there's revenue on the line here and I'm going to go get it, I'm actually going to be held accountable for it. So I better get it right. It's not an easy thing to do. And if you introduce it, you're going to be prepared for the fact that it's, it might look messy. But after a while you'll start to see it work.

Jeff: And operationally, [00:36:00] how does that work actually?. I assume it's not a one time thing. Here's what we're going to do this year. Tell me what it's worth and, go off, but how do you actually kind of line that up and drive that alignment and make sure they're educated and make sure you're educated on what they're bringing in.

And, I'm sure there's other people that weigh into in this process.

Jason: Yeah, you have to, this is across the organization. You got to bring in have a cross functional team that, you know, monthly stakeholders. So I like to have, I call it four in a box, right? Marketing, sales, product management, engineering, and you have these monthly alignment meetings and you talk about.

What you're focusing on and what you're building, how, what you bring into market and what you're able to sell, you've got to be able to talk about all of it. And you want engineering to hear all of that too. And you want sales to hear what engineering is dealing with because then it builds, a little bit of empathy in the room, for the challenges and also the accountability. That, teams have been on the hook to deliver. So I better do my part because other people are stepping up to the plate and. [00:37:00] Taking accountability and ownership. 

Jeff: I'm a sucker for a good soundbite and I love the, I love four in a box. I'm going to steal that and start using that because it's such a good Descriptive of what you want there. So I think that's one of my favorite things about doing this podcast is I get to learn all these different phrases that are maybe internal to one company or one, one person has coined and love rolling those out.

So that that's going on the list. Jason that's definitely going on the list. 

Jason: Remember who made that one up. I can't remember who told me that one.

Jeff: it'll be lost to history, but that, I think this brings together a lot of really good concepts. And one thing I've thought on and would love to get your take on this, maybe as a closeout is, I feel like in PE and PE funded companies. Everything was always focused on ROI and return on investment.

And what are we getting for this effort? Investment might be engineering time. It might be, sales effort. It might be cash outlay. But now post Zerp, 2024, this is something that [00:38:00] has rolled down our waterfall down to so many other types of companies. This is something VC companies are looking at maybe traditionally financed companies everywhere.

What do you think this kind of view on a more ROI focused world? At least in growing companies is going to look like in 2024. What does this mean? And how do you see this changing? Maybe what things look like as we go through this year and follow the following years, or is it something you just forgotten very quickly?

And, we returned to the meme.

Jason: No, I think we do need to take this seriously and think about the impact and I'm not an economist. I'm following rather than, what's going on, but the cost of debt has got, an obvious impact on investments and how companies are going to deploy their cash. The downside of that is it puts jobs at risk.

In some areas, I think some companies use that maybe as an excuse to do layoffs. I think, if I read the news of some of these layoffs, I don't think it's cause they have a cash problem. I think , they're using this as an excuse to [00:39:00] restructure. And redeploy some of their cash, which makes sense. But if we just think about this holistically, I think these are cycles, right? And I think this is as much as this can be painful. I think it's a good thing in the long run because it's forcing companies to build healthy, viable businesses. If the cost of debt is increased, then you're going to focus on having some level of profit.

You're less likely to go build a pump and dump business. That's still happening a little bit, I'm seeing, but it's less likely to happen and companies are going to focus on getting back into growth mode. And then when they feel like they've got the right level of growth, then they start hiring again.

And it's cyclical. So I think this is just a, a healthy but unpleasant or sometimes process. But if you don't go through it, then you don't set yourself up for success later on, use it as a time for making adjustments, pulling back in certain areas. . I visualize it like I've got a bunch of levers on my desk.

And [00:40:00] I'm pushing on one and pulling on the other and all this kind of stuff. And, when you have, this sort of post Zip world, you're just going to start pulling on different , levers and focusing a lot more on ROI as a key driver. And hopefully you pull through, right?

And you can get back to that growth that you're looking for and keep building your business.

Jeff: Nice. Thank you, Jason. This was fantastic having you on if people, are curious and want to reach out with questions. Is there any way they can reach out to you?

Jason: Yeah, LinkedIn is probably the easiest way I guess, these days. I suppose it's probably the easiest way. Yeah.

Jeff: Nice. Thank you so much. It's great having you on the show. Appreciate you taking the time.

Jason: Thank you. Thanks a lot Jeff.