Trust, Quick Decisions, and the "Gritty" Mindset ft. Jake Reni

I don't care whether you're a founder or if you're a first-time leader or if you're just a seller who wants to be better—like a better person—invest in yourself. And that's either investing in a coach or a therapist. It's worth the money, I promise you that.

And welcome back to another episode of the Revenue Reimagine Podcast. You are unfortunately joined by myself and Dale, and we have an incredible, incredible guest today. We're going to border on guest versus co-host. I don't know where to start. We have Jake Renny with us today. Jake is the Chief Growth Officer and co-founder at a small little company you might have heard of called Revenue Reimagined. We'll get into that in a little bit. Former SVP of Sales at Tiled, also ran enablement at a little company called Adobe, and has done all sorts of cool stuff, and balances out this thing I have to deal with all the time. Jake, welcome to the show, man.

Well, thank you for welcoming me, but I think it's not very kind of you to be so hard on Dale. I love Dale. I feel like that's an honor for me to be hanging out with y'all. I mean, listen, if it is a balance, you do balance us, and we could talk about that a little later. I think it's funny—anyone who listens to the show knows that all the joking is love. I have nothing but respect for Dale, and if it wasn't for Dale, I wouldn't have someone to be an executive assistant for. So like, exactly. Dale has provided me a job, so we're good, right?

So we're going to spin this a little bit differently today. We're going to start off and understand a little bit, Jake, on what you were doing, why you wanted to go into the fractional world, and then the second half of this we'll talk about why you want to actually end up coming and collaborating with us and playing in the space that's a collaborative fractional, for lack of a better term. But first, tell us a little bit about the origin story of how you came out from doing a bunch of work that you were doing and why you actually wanted to come into the fractional world to begin with. Yeah, what's that origin story for you, man?

I've been in the startup tech scene for probably the last almost ten years now, but before that, I did ten years of surgical device. But over the last ten years as I've been in the SaaS scene, what I started to realize role after role after role is that I loved building, I loved fixing. I was not a cog in the wheel. I didn't like once the system was all baked out and the process was all figured out, I found myself getting bored. And so I was always looking for an opportunity to have a bigger impact.

Once I got a taste of my first startup, I knew this was it for me. I wanted to do it. So I started with an early-stage edtech company called Instructure, and then I went to HigherView, and then after that I found a really awesome company called Consensus. And the trend was I was always either helping a company go up-market, down-market, or introduce a new product to market. And that was really fun. I realized like, okay, I want to document my journeys as I'm doing this to figure out like how can I repeat this over and over again. And then all of a sudden I had an opportunity to go to Adobe and do it all at scale. That was super fun.

Yeah, yeah. And I quickly took this tiny little enablement program from just the inside sales organization to this global program. We started with no inbound SDRs, to introducing a whole inbound program. And then we started from like two interns to like twenty-seven interns, and the program just kept getting bigger. What I realized there was a moment when I was at Adobe: oh my gosh, solving these problems are the same whether it's an early-stage startup or a company as big as Adobe. It's just learning how to solve problems that scale, which was kind of like the secret.

And then I went back into startups, and to sum it all up, what I realized is like I love doing what I was doing. I love working with founders. But the big thing for me was like if I wanted to help impact founders at the level that I really enjoyed without giving up complete control of that whole journey, I had to take it myself and I had to start my own thing so that I could help founders navigate some of these pitfalls that I was learning that were repetitive. And oftentimes they weren't willing to listen and learn from those journeys. They wanted to do things their way.

And so this was the moment for me: look, if I'm going to make an impact, if I'm going to do things the way I want to, and I can really make a change for founders and startups, I'm going to do this on my own.

It's funny you talk about the pitfalls and founders making the same mistakes, and I say all the time that founders pay us to say the stuff that they would fire us to say if we actually worked for them full-time. And it's true. Like, I say it in jest, but you're laughing—you're like, it's true, right? We get paid to give the real advice. But you said a few things that I think are really important. You talked about the challenges being the same whether it's Adobe, whether it's Consensus, whether it's Tiled, whether it's, you know, Dale's mobile boat wash or whatever it happens to be—new business for you, Dale—those problems are the same. Why do you think it is that founders haven't figured it out yet? Why are we dealing as fractional leaders with the same problems every time, every day, every company?

Yeah, I mean, there's something that is unique to the founder element of all of this in startups versus a larger company, and that is like rightfully so—every founder has identity tied to their startup, right? They have that, and that identity has ego tied to it. We all do. One hundred percent. All do. And so me, I have no ego. No, I'm kidding. Yeah, nobody has ego, especially the people who announce that they don't have an ego, right? Right.

So I think the realization is like when you're building something, especially if you're a technical founder, there's an element of belief that like I am building something so badass, so awesome, the world needs this. Do I really need to invest in all of this sales and marketing drama over here because my product should be able to sell itself? Because I'm solving such a meaningful problem. So oftentimes I find that it's like I got to the point where I realized I didn't even want to join a startup unless I knew that founder had already failed twice with two previous VPs of Sales because I needed them to learn that. They needed to learn those lessons because I didn't want to be the one teaching it to them.

Yeah, yeah. Well, you also didn't want to be that VP of Sales that came in and got fired because that's the point, like, because you're teaching it to them and so eventually one or two or three failed VPs, there's that moment of an aha of like that ego may be breaking and saying this business survival is more important than perhaps my belief of this. All right, let me go find someone that can hand-hold me through this. And maybe I'm going to listen a little bit more now.

Hey, we even got a thumbs up for that one. Yeah.

So one of the big rolling off of that question, one of the biggest challenges I think founders end up going through an evolution is their leadership evolution. What are three things that you would recommend to the founders out there as they evolve in the leadership evolution of a company from founder-led sales into problem-market fit or product-market fit?

Oh, three things that I would recommend for them as a leader? Well, this might be unconventional, but I'll tell you like I have yet to meet a founder that I've worked with who would not have benefited from an awesome therapist or a life coach. Hands down.

Yeah. Like, there were moments—there were conversations with some of the founders I love the most, and sat down and like, bro, you need to consider an awesome coach that's just going to help you think through some of this, right?

So I would recommend for anyone moving through leadership stages in their journey—I don't care whether you're a founder or if you're a first-time leader or if you're just a seller who wants to be better like a better person—invest in yourself. And that's either investing in a coach or a therapist. It's worth the money, I promise you that.

The second thing I would say is you know, hire people that you can trust.

# Transcript

To run the business with or without you, right? Especially at certain stages in the business where as a founder you have to go heads down. I need you focusing on fundraising. I don't need you in the business. I don't need you getting involved in deals. I don't need you obsessing about every little process. What I need from you is to go raise funding. So go do that. Trust that we can run it. Because I think there's a lot of things that get slowed down when we don't flatten decision-making and give autonomy to our leaders to actually go make decisions quickly. Early stage, we got to move quick.

And I would say the third thing is, you know, don't just assume that you understand what your sales cycle is going to look like or your persona is going to look like based on your previous experience or whatever it is. You really need to get in the segment and understand what it is the problem that you're solving and for who you're solving it. Because it's very tempting for a lot of founders early on to want to sell upmarket into the enterprise space. But I'll tell you right now, 99% of founders I've worked with were not ready for that. They were just not ready for that. The product wasn't ready for it. The org wasn't ready for it. The skills weren't ready for it.

So as a founder, as you're thinking through how you're leading your team into the next summit, don't be obsessed about summiting too quickly and tying that journey to having to be in the enterprise space with the biggest logos in the world. Sometimes that's not what's going to lead you to success.

**Do you have a philosophy on the timing of that? So every X amount of months, revisit it from an ICP perspective, buying persona perspective. What's your philosophy around that?**

I don't know if I'd say I like a locked philosophy, but what I tell you is, like, experience tells me, especially early stages, you're going through founder-led sales to product-market fit. You should, at a minimum, be revisiting this on a quarterly basis for so many reasons. You should be revisiting this every 90 days based on: Hey, how are we pacing based on the cohort of accounts that we're bringing in? Are we bringing the right kinds of business? How are we pacing from the unit economics of the way we're selling and closing business? Are we selling to the right persona?

I think every 90 days early on is a worthy timeframe to consider: Are we hitting in the right direction? And eventually you can pace that out. But what I'll tell you in general for a founder is you should never get to a point where you've paced yourself out of the business to the extent where you're not close to the customer anymore. I think that's a big mistake of convincing yourself that you still know what the customer wants because you closed two or three of the early deals and your buddies are at those companies and you're still talking to those buddies. And therefore you've convinced yourself that you're close to the customer. You got to stay close to the customer.

**And it's not going to probably be your like early buddies that you closed.**

Yeah. You said a couple things that jumped out at me. It's funny. I was talking to a founder this morning who is ex-Meta. She showed me a very MVP version of the product and she's like, well yeah, we're only going to sell to large enterprise. I'm like, might want to rethink that strategy. And by the way, they want to be bootstrapped. But when you talk about trust and not being involved in all of the deals and not being involved in every decision, and going out and focusing on fundraising, I personally have found that that's the hardest thing to teach founders. Whether I'm an in-house CRO, VP of Sales, or in our role now as fractional leaders, how do you build that trust and get that founder to trust you and your expertise to run the business?

So to your point, they don't have to be in the business. They could work on the business. Because I think that to me is one of the hardest parts of a founder—not even transitioning from founder-led sales of growing their business.

**You know, I would say it was probably like halfway through my career, early on in my leadership career, where it dawned on me all of a sudden: Jake, you are at managing up. And I was like, you know, I got to the point I was frustrated all the time. Like, why are they always up in my business? Why are they like, why are they inspecting everything I do?**

And what I realized is, like, your founder has no idea what you're doing day-to-day. They have no idea. They have no idea how many calls you're on. They have no idea how many partnership conversations you're leading. They have no idea how you're moving and shaking and hustling to grow their business. They don't know. And for you to just assume that they know because you're working your butt off, you're missing a really key point here. And that's you're not communicating up.

So there was one thing I learned—kind of like a moment for me. I think a mentor actually talked to me about it. It was like, Jake, how much time do you spend a week actually talking about your weekly priorities with your founder and then reorganizing those priorities with your founder to make sure that you're aligned on those priorities? And it was like, none. Never. I just jump on a one-on-one and tell them what I need, and then we argue, and I tell them, get out of my way, and then we go.

But the reality is, like, the moment that I started scheduling my one-on-ones to say, here's what I'm working on, here are my priorities, are these your priorities? Will you reorganize them for me? It changed everything. And all of a sudden I got trust and they started backing off.

People buy from people. That's why companies who invest in meaningful connections win. The best part? Gifting doesn't have to be expensive to drive results, just thoughtful. Soso's intelligent gifting platform is designed to boost personalized engagement throughout the entire sales process. Trust me, I led sales for a Soso competitor and I could tell you, no one does gifting better than Soso. If you're looking for a proven way to win and retain more customers, visit soso.com.

**Yeah, it's so interesting about alignment and expectations, but visiting them often. Like, when I coach younger, and I coach a lot of young leaders, when I coach them I'm like, "They're like, what's one piece of advice?" And I'm like, "Expectations early and make sure you're visiting them often." And by often, I mean like weekly.**

Yeah. Like, visit them weekly. Make sure you're still aligned. Because if you don't visit them for a couple weeks, you could be off by a factor. In this whole world—calls it the startup—that's like evolving super quickly.

**So Jake, you've been in both big companies like Adobe and a lot of startup companies. You and I first met when you were at HireView. Yeah. What's your, I always think that startup, the startup world is not for everybody. What's your philosophy around people getting into the startup world? People hiring from the startup world? Like, if you were a founder of this tech company, what are a couple of things that you think about when you're hiring the next set of groups that are coming in? Are you hiring people that have been in startups? Like, what's that hiring world look like for you?**

Well, first, to start with is like what I tell a lot of my sales reps. Because there's a lot of people who want to get in the startup world because it's being romanticized or their buddy—you know, I'm in Utah, Silicon Slopes. Do you know how many people along this corridor of this valley have a friend or a cousin or an uncle or whatever who has gone through some sort of an exit at a decent startup? I mean, the FOMO is real down here, right? And everyone wants to be. Everyone wants their story. Everyone wants that feather in their cap.

So I find myself in a lot of conversations with sales reps that I've mentored over the years or hired. It's like, look, there is no right profile of a sales rep in general. The idea here is like, what you need to know is there are reps who have certain personality and character traits and principles and styles that work well for startups. And there's some that are built and work really well for larger enterprise companies, just as there are some reps who sell really well into SMB and some reps who sell really well into enterprise.

So don't just think that a startup is for you or don't just think that the big company path is for you. Because if you love what you do and you find that it matches your skill set, you're going to do really well. And I know a lot of SMB reps who make a lot more than enterprise sellers because they're good at it, right?

So the first thing is like, find out how are you built. Are you someone who thrives in chaos? Does change affect you? Are you good at ambiguity and finding clarity and creating organization out of chaos? And can you move at a quick pace?

# Transcript

And can you work autonomously and sometimes be on your own? You know, sometimes those things might lend really well to being in a startup versus, are you super organized and are you thoughtful and do you like process? And if things are really thought through for you and laid out, can you just run and crush it? That means maybe you might be doing better at a company like Adobe or Salesforce. So just, you know, who are you and does it align with your skill set?

And when you ask me like specific characteristics, I would say in general there are certain things that I find to be consistent across all segments and all vertical types of reps. One: Are you curious? Do you just naturally have a desire to learn and drive yourself to be better? Are you having to be told what to go read, or are you the rep who subscribes to podcasts and reads all these books and nerds out or geeks out about your customer's industry? Are you subscribed to all of the newsletters in that space? Like, that's super critically important.

Are you gritty? And I think with grit comes this concept of having an abundance mindset versus a scarcity mindset, right? Are you willing to give and work hard and see things around you with gratitude? I find that gratitude goes a long way as a seller because we get kicked in the teeth and this job is hard.

Yeah, previous success is important, but we don't always have to go off that if there are other elements that come into play that I can teach you. I can teach you certain things, but I can't give you grit. I can't give you curiosity. I can't give you that humility that I think is really critical.

And then the last thing that I often look for is emotional intelligence. Gone is the day of the alpha sales rep who just kicks in the door and tries to control the whole deal cycle because they have this big alpha personality. What we're seeing is the introverted, empathetic sales rep who knows how to listen and ask great questions reign supreme because they're really good at running discovery.

I was just coaching someone the other day and we were talking about how their introverted technique has really helped them excel over those really outgoing reps on their team. He moved into the number one selling spot, and he was so concerned when he started. He was so introverted and thinking, "How am I going to do it?" And you nailed it. That empathy, that discovery, that listening is so much more now than the person who's like, "We're going to do this, and you didn't respond, so I'm going to send you a breakup email." We see it all the time.

Let's shift gears a little bit. So you've worked for a ton of companies. You decided to go out on your own and get into the fractional space. Everyone has heard Dale and I's story about collaboration and competition, but you could have done this not only by yourself but with a number of people. We were talking for several months, and it's no secret you were talking to other people as well. So two parts of the question: Why not do it yourself versus someone else? And why Dale and I?

Okay, so you guys are going to do this with me, right? I want you to close your eyes. It's probably going to be awkward for all the viewers, but close your eyes, and I want you to think about and see yourself on the summit of what success looks like in revenue or reimagined for you. Let's say five years down the road, and we've achieved something big, right? When you're standing there, do you see yourself standing alone or are you surrounded by awesome people you love?

Definitely the latter. Can't do it alone, right? I mean, you can, but I just have never. There are people who can run a million miles and do it on their own, just like we talked about earlier. There's not like one set style. I am the kind of person who wins together. I am not standing on that summit alone.

So when I thought about where I want to go and who I want to go there with, I knew it was going to be with great people. And that's the next piece was like, guys, I am tired. We have been doing this for a minute. We've talked about being recovering CRO, right? The biggest life lesson that a lot of the failures and the wins have taught me about being in startups is that you work with good people. Work with good people that you can love. You don't have to fake it and call them your family, but work with good people that you care about, that you are willing to sacrifice for.

And not like, we have a whole different conversation when it comes to loyalty, but that you can trust.

I was just going to say that's the most important word to me.

Yes. And so when I sat and thought about that and some of the conversations I was having, you know, we've known each other for a minute, Adam, but I've known Dale for a long time. And I have been through some ups and downs in my career, and I'll tell you, I was talking to my wife about this just the other day. There have been some shitty moments in my career, some dark moments, some lonely moments. And the one person who was consistently checking in on me, texting me, asking me how I'm doing, building me up—well, yeah, yes, Wendy, if you're listening, I love you—but Dale. Dale, I've got friends that I grew up with that live close to me, and within a 20-minute drive, Dale checked on me more often than they did. It's not because they don't love me, but it's like Dale cares and then this dude gives a damn and he's genuine about it.

And sometimes when I was down, when I didn't have anything to offer Dale, you know, Dale was there saying, "Bro, how are you doing? What's on your mind? Let's get together on a call. How can I help you? What are your thoughts about this?" It's just like that to me is beyond real, and that's the people I want to surround myself with.

You nailed it. It's so the trust is important. I'm not a big fan of the word "family" for a plethora of reasons. I think a lot of companies overuse it, and it's like your family until we don't need you anymore. I think it's different when you own your own business.

But I've talked about it, and listen, it's like Dale and I disagree plenty. And we can certainly get to the point where both of us could be a little snippy with one another, but it is like family because then we come around and we get on the phone and it's like, "Dude, come on. That's not what I meant," or "That's not what I meant. Let's figure it out." And the next minute it's like, "All right, let's go figure something out and build a business."

And I think that is what I was looking for when I was looking for a partnership, and that's one of the things I really felt instantly about talking to you is just this instant sense of trust. I could be wrong, but I don't doubt that if I were to say to both of you, "My kid's sick or my wife's sick or whatever and I can't do whatever and I need you both to be in West Palm Beach tomorrow," I have no doubt you, Dale, would drive and you would be on a flight, and I would do the same for either one of you.

And I think that's the benefit you get when working with people, and I think that's also the benefit that our customers get. Because when you look at it, you have three people who are as committed to each other and to your business to seeing it succeed that you might not get with one person. And I think we have that conversation and we'll work out a lot of stuff behind the scenes for our clients.

That was my aha moment when Adam and I started to partner because I never really thought I would partner with anybody either, but it was always like, what I realized when we tried this out, we tested it out, was the collaborative fractional piece. Because us as fractionals, it's a super lonely place. I see so many fractionals from the whole—from marketing, revops, sales—going back full time because it's just super lonely. And we're very much people that like to have other people around, have conversation, and you have that camaraderie. Like, you do miss that, but on the back side of it, when I was struggling on an account or trying to figure out a comp plan or trying to figure out something, it was so much better as a partnership to be able to call Adam up and say, "Hey, Adam, do you have this document? What about this SOP?"

Do you have a comp plan that looks like this? Because if not, as an individual, if you're solo, you're always calling someone and asking a favor. It's always like you just end up running out of favors to ask. And there's communities and everything, but I just think, you know, having someone weekly, someone that has the experience, and because we have similar experiences yet different points of view on certain things, it actually gives a lot more value to our clients. And I think, you know, moving into 2024, one of the things I've been talking with a lot of analysts on, like go-to-market partners, it's been so top-heavy with hiring leaders that they're going to start hiring fractional leaders and have people actually doing the work. It's going to be like this inverse effect.

Last thing I wanted to say before we kind of jump into something else was when I was closing my eyes and looking at the summit, I was thinking about when I was at the top of Sundance and wondering where Adam was and just knowing that he was not at the top of Sundance with me. So that was so—but you wanted him there. You wanted him there. That's the point.

Yeah. Dale is in a backhanded way giving me grief because I didn't ski a black in Utah and break my leg. At least that's how I'm taking it. Maybe I'm wrong.

No, it was just the whole process of it. I mean, to your credit, I think it's a double black diamond, so it's not like it's not for the faint of heart. But no, listen, on the top of that hill, like there's no one else I'd rather be with. Like we can moan, we could fight like brothers, but at the end of the day, like we come back and do what's right for each other, do what's right for our clients.

Yeah, and that's how we roll. 100 percent.

So yeah, go ahead.

I was just going to say, on every show we believe in giving more than receiving. So like we're not going to do something different on this show just because we have one of our own co-founders on with us. So Jake, tell the audience what you're going to give away.

Okay, well I have a 15-year-old teenager that I'd like someone to please take off my hands. Come on over. Dash, we got you. Just kidding. Just kidding.

No, just kidding. You know, I would love to give away an hour of coaching time with a founder who's thinking through some of their challenges and go-to-market or anything related to principal leadership. So I'm giving away an hour of my time for a one-on-one coaching session.

There you have it. I love it. This is a great way to see the newest co-founder of Revenue Reimagined. All right, let's dig into some rapid fire before we wrap it up. We're not going to change it up today. Jake, if you are not in tech, no tech in any way, shape, or form, what profession are you going to work in?

My wife already told me what it would be. We'd have a mini farm in the middle of nowhere and we'd be taking care of mini goats and mini cows and mini horses. That's what she told me we'd be doing.

Yeah, that's what she wants. These hands are too soft, so I've got to rub them up a little bit. But if I wasn't doing this, I'd probably follow her dream on that one day. But I think if it was my choice, I know this is super different, but I would just love to have my own shop in the middle of town like helping create experiences for people to do the kinds of things they love outdoors. So I'd be doing something totally different.

Yeah. What's the first app you check when you wake up in the morning?

All his text messages from us.

Oh, yeah, it's usually I wake up to like 12 text messages from you guys on the East Coast. The first one I typically check is weather, and then the second one is probably my email, which is so bad. Like I need to change that up.

What? Are you an early bird or a night owl?

I've always been a night owl, but I am slowly, like with age, becoming an early bird. It's just, I think it's just happening.

Okay, last one. We wrap this one up. Dream vacation destination.

Oh, we've done some ones recently, but I think top of my list right now is probably Machu Picchu. I'd love to go hike that like three days on the Inca Trail. That just seems epic.

Very, very cool. Sweet. This is the first time, Jake, that you've been on the Revenue Reimagined podcast. It will not be the last. Stay tuned for some more information on that. Thank you for joining. Thank you for chatting all things with Dale and I.

Go check Jake out on LinkedIn. Jake Reiney at Reimage. And of course you can check us out at RevenuHenreImagne.com. Jake, thanks for joining, man.

Thanks for chatting.