The DO's and DON'Ts of Go-To-Market Strategy for SaaS ft. Jenn Steele

I am ruthlessly practical. If all you have is innovation without execution, you have a daydream. You don't have a company.

Welcome back to another episode of the Revenue Reagin Podcast. We are so excited today, not because we have Dale here, but because we have someone who I consider a friend, someone who I've worked with, the amazing Jen Steel, who is the CEO and co-founder of Sound GTM, former CEO of Kissmetrics. She's also held CMO and C-level roles at various different startups, bringing a great blend of sales and marketing expertise. Jen, thanks for joining us, and sorry you have to put up with Dale. You know, I love you both equally. Maybe. No lies. Want to hear that? That was the last thing you wanted to hear. You're every sales suite. So it's going to be a great episode.

The first thing we like to do when we talk to new startup founders or any startup founders is to talk about the origin story. So give us a little background on Sound GTM. I know it a little bit. I was like, Dale, you've been helping out a lot in the early stages. But we love to give you the origin story of when you came out of Kissmetrics, your thought process around it, and where Sound GTM came from.

Absolutely. And I'm going to tell the story a little bit differently because one of the stars of the story is on the call here.

I sold Kissmetrics at a profit in May of 2023. And once I caught up slightly on sleep, my primary investor from Kissmetrics said, "Hey, I have this platform. Do you want to take it to market as a new startup?" My first answer was no because I wasn't interested in it at all.

Then serendipitously—I think it was through Rev Room—we were having a conversation on partnerships, but also like how partners and affiliates and what does this ecosystem look like that's basically becoming the gig economy for sales. And I had a bit of a light bulb moment and I said, "Wait, what if I could actually be a major player here in the gig economy for sales and help out my friends who were dying for pipeline and my friends who are dying for a job or a boat or something like that?"

And I was like, "Oh, but that sounds like a pain in the butt." And then—and this was all Dale's idea—Dale is also an adviser once I finish the paperwork to the startup. So full disclosure here, Dale said, "What if on the sales side we build out that side of the marketplace by partnering with communities?" That's when my answer went from "No, I don't want to take this product to market" to "Well, first I investigated a little bit. I talked to a bunch of CMOs. I talked to a lot of people who would be part of it because you have to do user research." But that's when I moved from no to "Hell yes."

And so it has taken longer than anyone ever wants a startup to take. We meant to launch to alpha in December, got hit by a bunch of regression bugs. But hopefully we will be in alpha and beta and all the way to market because of course it's a platform that was already mostly built. We just had to make some tweaks to it. Any day now. And I'm hoping that Dale and Adam will help me beat up the platform a little bit, give feedback. All that jazz.

We definitely will. And it's an interesting story because I actually got behind the scenes a little bit and understood a little bit more on some of the investing side, some of the cap table side, restructuring some of the pieces. It's been a very interesting ride. But I almost killed a lawyer, you know?

Yeah. I wouldn't kill a lawyer. That one's going to be tough.

Well, luckily he was in Florida. And no, he wasn't in Florida. You were in Florida. He was in Texas, and I was in Seattle. So I wasn't willing to get on a plane to kill the lawyer. But now the paperwork's done, the cap table's done. I swear, Dale, I'll get you that advisory agreement any moment now.

It's all really—why is Dale getting an advisory agreement? Like, hello? To your friend idea was his. I haven't discounted you, Adam. I just—I don't—I haven't yet to see a good idea. No, I'm kidding. We would not function without both of you. You know, it's funny. You talk about killing the lawyer, and you talk about the struggle and the cap table. And I think a lot of people—and you're probably the earliest stage founder we've had on the show so far, right? I think a lot of people don't realize that once it's seed, once it's like, "Oh, we're selling product. We're talking to customers. Arguably there's revenue coming in the door." But it's super early. And as you know, you're starting. There's a lot of assumptions that people have of what it takes to build a startup. Right? You get noise from your advisers like Dale—that's probably bad advice. You get advice from your VCs or your investors that likely could be bad advice. There's the public that wants to give you some more bad advice. What are some of these assumptions that are just like these commonly held beliefs that people are telling you, "Do this, do this, do this," that as you're building Sound GTM, you're like, "No, all of that. None of that matters. I'm going to do this my way"? What advice did you deliberately say absolutely not?

Oh, dear heavens. There's actually a very long list. Not all of it. I actually just talked to somebody who has given me an idea on how to fundraise more quickly so I can get into what I'm good at, which is selling product once we have one.

Most of the startup advice out there is completely aimed at 26-year-old Stanford graduates who have coded up something that might not have product-market fit. They've never taken anything to market. They've never presented to a board. They've never worked with investors. They've never done any of this, which means most of that advice is completely useless to me—someone who has been in the startup ecosystem since I joined HubSpot back in 2009, someone who has sold a company as CEO, someone who has presented to a bunch of boards, and who has specialized in go-to-market roles, not R&D roles.

So most of the advice is like, "Uh-huh." Like, "You need to talk to people to see if you have product-market fit." Uh-huh. Yeah. So like, one of the very first things I did—as I probably mentioned in how this came to be—I was like, "Okay, so there's this thing. There's an idea Dale has. An idea to make it a real idea. Let me talk to as many people as I can." So there was a forest conference happening in Austin. There was a Chief Marketing Officer event alongside of it. And I could get invited to the CMO event. And it was this lounge thing, and I basically spent three days in Austin in a lounge talking to everyone about this idea. I hadn't touched the product. I hadn't seen the product. Hadn't touched a line of code—not that I really want to touch a line of code. I hadn't done anything before I made sure that there was a need for this product.

And of course, as time goes by, it seems like the need and the desire for both sides of this marketplace is higher and higher, which makes me more and more frustrated as I haven't launched yet.

But some of the advice is good—"Go talk to customers"—and some of the advice is just dumb because it's like, "Uh-huh. I already know how to do that. I've already brought products to market." And then some of the advice I can't execute because I'm not a 26-year-old founder, right? "Oh, you just need to bootstrap." I'm sorry. There are mortgages and things like that that were done back when I had a salary. It's not the same thing to be starting a startup as a grown-up, as it were.

Of course, you guys know this, right? You're starting. You've started your own. I don't know. Adam's not growing up yet. So I don't know.

So I realized—yeah, go ahead. How is it like going through all the stuff? So if you go back through your CMO, CRO, CEO, and now founder, how has that leadership evolution changed in that process? Like, where are those evolutions from, okay, we have marketing, we have sales, now I have a CEO, now I'm CEO that needs to sell a company. But now you're kind of at the bottom again. How is your leadership going to evolve through this process?

I will say that I have the advantage that when I moved into startups and into go-to-market, I actually had already been on the executive level in a completely different industry. So granted it was the legal industry and I had to have the pole surgically removed from my rear end before I was an actual effective leader. But I think for me, the most important lesson learned and the most important evolution that I came to when I became CEO is: Why do I have other executives anyway? And I say that all the time, interested. But not for the reason you think. It's that we need. So founders hire executives and then don't do what they need to.

Do with them. So if I'm hiring another executive, it's to do one of two things. One is I can't—I don't have room on my plate for this thing anymore. I need someone else to own it and build it and use the strategy. I'm going to use marketing as an example because I've already gotten fractional marketing help for my company. I like to think that I was a damn good marketer, but you're all right. Yeah, sometimes you're pretty darn good at what you did. Yeah, I can run a playbook, but seriously, I was an expert at messaging. Yeah, I was an expert at messaging, at branding, at things like that. But when I had to do it for my own company, I was doing that and 12,000 other things at the same time. And I finally put up my hand and talked to a friend of mine who I knew understood my voice and stuff, and I was like, "Help." So it's something I could do, but it's something I had to get off my plate. The other reason for a CEO to hire an executive is because they can do something we can't. So there will come a point in time that I need to scale sales past my own experience and understanding. Right. That's when I call you guys. So yeah, and that's so interesting that evolution, right? Because it's like what you said was very interesting. Even though you had the ability, there's two things: it's either the timing of it or you need something adjacent to it. Like, I know how to do X, but if I do X plus Y, I can get there much faster, right? And so I do think going back to the original challenge—the assumptions people are telling founders to hire people just because, "Hey, you should go hire ahead of sales. Hey, you should go hire ahead of marketing"—yet there's no strategy put in place yet. And not only does your head of sales need to build a strategy, they need to close deals and they need to get pipeline. And it's like, "Okay, so then how does that head of sales go get that help?" Right. And then there's the trust. And I know I have lived this. I know Adam has lived this, and I assume Dale has lived this, where they're like, "Go do this. You own it. You are the CEO of your own department, whether that's sales or marketing or whatever." And then you're like, "Fine, this is what I'm doing," and they're like, "That's the wrong way to do it." And I'm like, "You've never done marketing before. How the hell do you know that's the wrong way to do it?" "Well, it's not how I would do it." You're a founder. I once ran both sales and marketing at this tiny startup, and my CEO was really frustrated because nobody was replying to the sales folks' emails. It was a small enough deal—we didn't have the BDR model. It was like a straight inside sales model. And we'll come back to that. And this was also back when, like, in the days that Predictable Revenue was a new book. So my CEO turns to me and he's like, "Why can't they get their emails replied to? Everybody always replies to my email." And I said, "Really? What's your title at the bottom of that email?" He's like, "CEO." I'm like, "Uh-huh. Right." And that's exactly it. And people don't realize that. And it's funny—I literally Jen just posted about this today. It's very different when you reach out to someone as a founder or as a CEO. That whole founder-led sales motion, you get access that Bob the account executive or Dale the VP of sales or Adam the BDR doesn't get. And people don't necessarily realize that there's this transition that has to come into play. I want to take a step back. So I had the pleasure of working with you not that long ago, like a few years ago. So I know your capabilities. I know what you're good at, both on the sales side and the marketing side. You led marketing. You probably should have led sales, but that's a whole separate conversation that requires a few more beverages. Yeah, a few more beverages. And we don't want to upset people today. But having been a senior-level C-level executive for multiple different companies, like, what in the world made you say, "Hey, I want to take the stability of—I'll give a range—three to $700,000 a year job, depending on what stage you're at, right?" You both seriously to go start something on my own and take this risk and build something from the ground up that hopefully works? And like, we want it to work for you, but let's be real. Most startups aren't successful. Why take that risk?

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Instead of going and doing it all over again, there's the tongue-in-cheek answer, which is I am overeducated, I don't have kids, and I have ADHD. And so what else am I going to do? I like it. But start a startup? Why not? Truthfully, I never want to be a CMO again. Okay, tell me more. Or a CRO. I had it up to here with the bullshit. I was so tired of a founder saying, "We need to message the company this way," and I'm like, "That's how you pitched it to investors. Investors are not our persona." And they'd be like, "Well, I know our persona better than you do." I'm like, "How many have you talked to? How many sales calls do you listen to this week? Because I listen to 12, and I'm the head of marketing." So it's a dreadful role, honestly. I mean, the head of sales is a dreadful role for a completely different set of reasons, but let me talk about head of marketing. Everyone thinks they can do it. It is the most cross-functional and wacky-ass team there because you've got short-term deadlines, you've got long-term deadlines. You have RevOps, who's very data-driven, and demand gen, that's very data-driven, and then you have branding that's like, "And now we're going to turn it pink." And they might be right, but you're managing both of these people at the same time towards the same goals. It requires—honestly, that part I found fun because, again, with the ADHD, I have the mental—I love the mental gymnastics. But the complete lack of understanding that marketing has to do a lot of different things, and that one thing that's on the founder's mind might not be the best thing for us to do. And how many times do you live that? And I got tired of it. And really, there are times that I look at my dwindling bank account since we have been bootstrapping, and I say, "Well, maybe I should go back and be a CMO." And then I go look at my CMO Slack and see all the pain and frustration that I have lived, and I'm like, "Oh, hell no. Like, no." It is tough. And a lot of the challenges that you're talking about, I think it's funny because I think a lot of the people that do start companies or the founders we do talk to, they have this sense of like they want to change stuff. They don't really want to go back into it. They don't want to report to anybody. They want to kind of do something that they've always thought about doing. And it's funny because when Adam and I started Revenue Reimagined, it wasn't that either of us necessarily were looking to start a company. What we decided was there's got to be a better way to help more people. And so you get into a place of like a—and the same time, a bit about what you're saying—because we were both leading sales teams. It becomes very difficult because the founder would always pitch us like we were investors. I'm like, "Hold on, time out. We're not your investors. We know whatever you're doing is broken, or else you wouldn't be talking to us." And I think that message needs to come across to founders: it's broken, and it's okay. You get the right people, and you talk to the right positions, and you're going to get there much faster. So I think have some humbleness in that process and know that it's broken, and know that people really do want to be there to help you.

Yeah, yeah. I mean, you have to muscle through, though. Like, being a founder is rough on the ego. And so that's why—and actually, just like you guys—I didn't mean to found a company. It just so happens that I can help a lot more people I care about with the company that I've founded. And so that's what gets me up in the morning. But that also means I don't necessarily have that ego to take me through when an idiot VC says something about, oh, I don't know, and I'm just like, "Will not respond. Will not respond." So I can't blame the founders for being very like, "I'm right," because this is hard. Not going to lie—you guys know it. It would have been a little bit easier if I had started like almost consulting and then built a product, but that's not the way I started it. And so blame me.

But I think it's interesting because when founders hire you guys and believe me, I am very excited to someday hire you guys. Because actually, when I was very first founding this company back in the dream stage, I was like, "But I don't know if I'd rather have Adam or Dale as my head of sales." So I'm like, "Hey, hey. I mean, really, that's not even a question. Let's be real here. You want Dale as your head of sales and me as your head of RevOps." "Go yeah, now you're thinking!"

But by the time a founder hires you, they know something's wrong. But it's how do you get around that ego that they have had to build up to survive to where they are now?

Yeah, that's the tough part. Interesting perspective. This question is interesting because I know a little bit behind the scenes. Innovation versus execution. Because there were a lot of things as you're building this product out, and I know a little bit about it, where you had to balance like getting to market, getting there fast enough, yet taking the product that you have plus injecting the innovation. Some of the things that we were discussing in the process and we were like, "You're like, yes, I want to do that, but I gotta get the product market first." How do you balance that as a founder as you're trying to also balance the lawyer that you're looking to kill and like the market people you're trying to hire and all that kind of stuff?

Dale, you're right. You already know this. I am ruthlessly practical. If all you have is innovation without execution, you have a daydream. You don't have a company. I love that.

And so, you know, I love all the ideas. I've got more and more of a roadmap with ideas daily. I need to share with you the most recent one. But there have been times that, and Dale can tell this to you too, Dale, you've been like, "What about this?" and I'm like, "Nope, not going to happen. Outside the scope. Great idea. Go find somebody else."

You have to, though. Especially in the early days. And listen, I worked for a company that wanted to be all things to all people and built what I call vaporware of like Figma screens pretending that we had it because it was like, "Well, if someone wants it we'll do this, and if someone wants it we'll do this, and if one person wants it we'll do that." And if you're not ruthless about the problem you're trying to solve, you become decent at a whole lot of stuff and really good at nothing.

Yeah, well, that's like I am attacking. So, you know, this marketplace I'm planning to sell to B2B SaaS companies, probably sell initially into demand gen or whoever handles the top of the sales pipeline. My platform can actually support everything from newsletter signups to AdWords to close-one deals. But that's not what I'm going after. And then my beta list got so big that I'm starting to verticalize. So I'm going to cut off certain verticals. And it's choice after choice after choice because if I try to be all things to all people, nobody knows what I'm selling, who I'm selling it to, and why they should give me money.

I realized I am totally preaching to the choir because you can't sell a product if nobody knows what the product is and what they use it for. And you know what? If this one use case doesn't work, even though it seems like a very probable use case, then we pivot. It's part of why the company is called Sound GTM and not like "Go Find Leads" or something like that.

Yeah, it's so funny that people don't think about the basics. And at the end of the day, it really is. And Dale and I use this term a lot: you have to have the foundation first before you do anything else. And everyone wants to go off and not build the foundation and start like it's we're going to build the skyscraper in the sky and work our way down. Like, you can't do that.

My question: you and I both worked for a startup that was blessed to have a lot of money, right? Sixty-four, some odd million dollars of memory. Serve. Correct. Yes, total of eighty-two. Who's counting? Yeah.

Oh yeah, I have never spent money like—like when the CEO turned to me and said, "Spend three million dollars in that quarter," I ran the Series D playbook. We had no business running a Series D playbook, but I didn't know how else to spend money. You spent it. Oh yeah, I mean, everybody knew about us for a hot second, but in that pursuit of rapid growth, it's balancing that scale and that grow desire for scale versus sustainability.

So when you look at building your startup, what is your mindset and your thought process for how you're going to balance the need to scale, how you want to scale, but still remain sustainable and steady? Because slow and steady wins the race, right? Or does it?

I think managing a business like a real business and not like, "There's money for you and there's money for you and there's money for you and then oops, no money." But for me, it's what I had to get down to brass tacks. My platform is a marketplace. A marketplace lives and dies on keeping supply and demand both balanced and growing. How the hell do we do that?

So I sat down for a long time. Thankfully, Dale had the brilliant community idea and for geniuses, really all in, to help us with this. But it's like for me, I'm not even thinking—I'm not thinking scale yet, although he knows I'm fundraising on it. But I'm very much like, "We need to get this going and we need to get the flywheel going." Because once you know how to sell, once you know you've got product-market fit, and just because I got sixty-two companies on my beta list, yay, doesn't mean I know I have product-market fit. I mean, that's sixty-two companies who buy into the gen vision. That's all I know.

Yeah, well, absolutely. Listen, people buy into right? Like, investors invest in great founders. We have any now that we're working with, and I can tell you like, I don't know how D feels, but like for me and it's the call we were just on there—the founder is what sold that to me. Like, he is so infectious and so personable and like loves this product. And it's like I can get behind you if you're selling paperclips, dude. You're a—yeah.

Yeah, and I think part of the reason so many marketers are like, "Yes, put me on the beta list" is because they're like, "We know you have lived our pipeline problem and we know that you're going to do your damnedest to fix it."

One hundred percent. Yes, so true.

Yeah, but that doesn't necessarily tell you much about scale. Except that I will also say, having worked at Kissmetrics where we did not have venture funding and I had to manage cash, let's just say that I don't think I'm ever going to forget those lessons. So they will stay with me for a long time.

Exactly. Well, you've been on both sides of it, so I think you can take a bit of it, everything, and then you can kind of blend together.

So at Revenue Reimagined, we enjoy giving back as much as we enjoy receiving. So one of the things that we like to do is our guests love. And you're a GTM geek as you self-proclaim, so provide the audience with what you'd like to give.

I am so passionate about helping people with their go-to-market. Especially if you've got founders out there who—and I'm not going to take your business, trust me—but who are just like, "What do we even do? Like, how do we even figure this out?" Or somebody, or even if you're a CMO that's like, "How do I convince my CEO of X, Y, or Z?" It's like I'd love to sit down with you for an hour and see if we can talk it through and work it out. It's a really fun hour for me and hopefully useful for you.

Love that. I love that. I love it, Adam. Listen, I have to put up with you and balance your ideas, so I could take all the GTM help I can get. You know, I'll talk to you anytime, Adam. So I love it.

I feel like we haven't spoken in forever and like we could sit here and chat for the next hour. I had fajitas the other night for dinner and thought of you.

Yes, but I think we've covered a lot of really good stuff today for people again who are early in that founding journey or even those who are late, who like are doing a reset or a reboot or just taking some time to reflect. As we wrap up, I want to dive into a little bit of rapid fire.

The rules here are ten words or less. Otherwise, Dale hits the gong or the gong comes along the side and hits Dale, depending on which kind of mood we're in. Preferably the latter of the two.

Okay, all right, here we go. If you cannot be in tech anymore in any way, shape, or form, what profession are you going to be in starting tomorrow morning?

Marketing consulting to non-tech. Too close, too close, fine. I'm just going, no sales, no marketing, no tech. Like, you have to be like a chef or something.

I mean, no, be a chef. But you know what I mean?

A sailor.

Who am I kidding?

Like it. All right, I like it. I like it. Okay, so this is perfect for you. Where do you start first—sales or marketing?

Yes, great answer. They're the same damn thing at first. Who are you selling to?

I'm sorry, I'm going to blow up the ten words. Never mind, go for it. Go for it. Who are you selling to? How do you have to talk to them? Where are they? Where do you have to be?

Love it. I love it. Jen, what is—other than your iPhone or Android? No, we don't use Androids on this podcast. Other than your iPhone, what's the one tech gadget you can't live without?

Probably my Bose Bluetooth sports headphones because I'm constantly on calls. They record half decently, and even though Bose can't figure out how to make things connect correctly for Bluetooth, I am again failing the ten words.

Um, there you go. Early bird or night owl?

Early bird. Like it. I mean, I have to talk to you guys on the East Coast all the time.

Yeah, it's true. Yeah, I mean, listen, absolutely. What's the song that gets you in the zone for work?

Um, Fallout Boy—"The Light Them Up Up Up"—or "The Distance" by Cake. My daughter's a big Fallout Boy fan, so she'll like this one. Okay, last one. Dream vacation destination?

Oh, we want to go to Italy, um, specifically Northern Italy.

Oh, I thought you were going to say the Amalfi Coast.

That too. All of it. All of it. But Northern Italy is great. Having done both, Lake Como, I think, is much better than the Amalfi Coast. You don't get near the traffic, and it's just a whole different experience.

Yeah, and very different vibes up there. So yeah, sorry. Yes, Tuscany, Florence. Yes, um, it's incredible. I am so grateful that you came and chatted it up with us for half an hour.

I am grateful that it was half an hour. I didn't have to spend a loan with Dale. You dropped a ton of knowledge. Where can people find you? Where can people find information about your startup?

Sure. Um, easiest place to find me is on LinkedIn. That's linkedin.com/in/jen-steel. J-E-N-N-S-L-E-E-L. And my startup has a non-ghastly website finally, and that's it-sound-gtm.com. Go check it out.

Jen, thanks so much. It was a pleasure.

Thank you. J, so much. So much fun to talk to you guys. Thank you so much.