From IPO prep to mid-market leadership: hard lessons in accountability with Rob Freedman

Hello, hello. Welcome back to another episode of Executive Conversations. My name is Maiva Cifuentes and I am your host. I am the founder of Flying Cat, which is an SEO and content agency for B2B SaaS.

In this podcast, Executive Conversations, I talk to marketing and GTM and sales leaders about the behind the scenes of what's going on right now in growth and in marketing. So much is changing in 2025. I'm really excited because today I have Rob Friedman, who's the VP of Marketing at Evo and who has been in senior leadership for a decade or longer in marketing. So I'm really excited to kind of talk about how things have been changing and just dive into his experience.

So let's just jump into it. How's it going, Rob? Doing great. Thanks for having me.

I'm excited to have this conversation with you. Yeah, same. We already started kind of getting into it and then we're like, oh wait, we better record this is already quite um quite interesting um you were already saying about how the i think the last thing before we said we need to start recording is you were saying how it's harder and harder and harder to justify any kind of brand budget decisions yeah yeah the getting those those of brand dollars for big brand campaigns, I think, in your startup world, and especially for B2B SaaS startups is more and more difficult to get that, especially in your PE and VC-backed companies.

Is that different from what it was before? yeah i before when i was with a couple you know earlier companies and it was all about the brand first it was all about hey let's do a big splash in our go-to-market and big advertising bigger advertising spends let's do a campaign let's do this and even though they knew there wasn't going to be that direct, clear, clean line of sight to revenue. So the ROAS was going to be bad, but you knew that going in because you're building a brand, you're trying to get name recognition, you're trying to get in front of your audience and introduce this new company.

And now I find that there's a little less energy and enthusiasm around those types of projects than there was, say, a decade, 10, 12 years ago. Is that a shift? So is that because the executives were maybe more hands off before and it wasn't like the CFO was involved and now the CFO is involved or is it the marketer or like where has that shift happened, do you think? Yeah, I think part of the shift is the type of leaders that were in these roles.

So if you got like a decade ago, you had senior leaders, CMOs, VPs, who were more generalist, and they probably came from a wider background and had experience with a wider variety of marketing types of activities. so in those roles and then I think other senior leaders on the leadership teams were less involved you nailed that part I don't think CFOs ever had a really close one to one with me until probably in the last definitely in the second half more recent half of my career whereas earlier on it was CEOs, mostly it was marketing lead, CEO, maybe board but that's about it But yes, CFOs are definitely in the conversation much more now and other leaders too.

Product much more involved than it was originally before. It was like, here it is. Go market it. Now there's much more collaboration, which is a good part of having more voices in those marketing campaign decisions.

But I think now the increased complexity of digital marketing and the rise of new channels has certainly led to some of this shift away from brand because now you can get a measurable impact much faster through like paid channels and things. So I think part of it is, is moving that over where, you know, CMOs and VPs and marketing, you know, now have this different focus. And instead of this more overall vision, it's very like, how are we going to build a high performing special, hyper specialized revenue focused team?

And so I've had to make that tactical shift in my own career and become much more revenue focused and sales friendly. I think. So there's been some good that's come out of this shift. I miss working on those big, splashy campaigns, and I do highly value brand.

Long term, you need to build your brand. But the good part that's come out of this is the synergy between marketing and sales. Your entire customer lifecycle. So everything from product to marketing to sales to customer success and that whole loop there, having all those teams aligned and working together, there's some magic that happens out of there.

It sounds like you have the experience that then shifting away from brand campaigns and more into this performance side is actually just better, more effective. Is that what you're saying? it can be in the short run in the short run, which is what a lot of VC backed companies are really aiming for is okay. How can we get squeezed the most growth out of our investment as possible?

And if you're going to spend 250, half a million on a big brand campaign and not be able to tie it back to directly to some significant revenue, that's going to be a very tough pill for the dc to swallow or like so i gave you five million you just got one million on ads billboards what are you what are you going to show for it so i think that you know that this then over you know back then uh data was important of course technology was important but now everything is a data decision and if you can back up your decisions with data you almost like laughed at it Yeah And I uh and now like the billboard campaigns and things that kind of like that what you use with your budget when you got left over that's what you use when you're trying to support something else like maybe in a key event or something that you're trying to do like uh and i did this at a couple of previous places where we had billboards at events with competitors or did like uh those like taxi cab wraps and stuff and was doing some promos around that but it was all in support of something else larger that was hyper measurable right okay so the brand campaign itself wasn't but it was supporting something else that was and you had the outcome there exactly um and now it is quite interesting how everything is becoming i mean like you say everything was data driven before but i do feel like even when i started the agency five years ago i could close a deal with an idea like a vague idea or We're just saying, here's how I do things.

And now I have to have very exact data-driven plan before I even close a client. Well, yeah, I think that is the rise of that, our digital first marketing, omni-channel marketing is really. So you had your more traditional channels that were print. Oh, geez, who's doing that still?

Really, not a lot. especially not b2b sass uh so but you had like direct mail you had your uh digital you know just still digital marketing but it wasn't the central focus now it's all digital really and and even anything you do in the physical realm of things you know we're doing like uh you know abm gifting platforms and stuff are highly measurable and still digitized and measuring the outcomes of those uh now seo i mean seo and now llm seo which i caught your last uh session on by the way those great great insights i think half my team has been is they are loyal subscribers so thank you and uh and so that you know social content all these things come together and create you know, the omni-channel now that we didn't have that before over a decade ago, you, it just, you didn't have the tools and the technology to pull that all together.

And now you do. When, so you mentioned earlier, um, that you have to provide the short-term wins. And I was wondering, uh, because I, I see a lot when you're speaking to a manager, they're thinking about the next quarter, but when you speak to a CEO, they're thinking about the next five years sort of thing. But I haven't really seen that in practice because I feel like the content marketing manager might be thinking about the next five years and the CEO is thinking about the next quarter.

Yeah. How are you seeing that? I see a lot of the same thing. I think depending on how on the management framework that the company is built on.

I think the newer, younger startups, your series A through C startups, they're very much living quarter to quarter. They're living round to round. They are looking for, I think, the age of spend, whatever you need to spend to grow. Those days are gone.

so I think there's a tighter controls and accountability and I'm not afraid of accountability I think accountability is good but I think due to that shift where it was hey you got your series a your series b now let's just go spend it let's just grow like crazy and we'll sort out the the row as uh later and okay so your cacti LTV ratio is a little off but we're growing we're gonna get next round. Well, that's a series C problem. That's a go public problem. Those days are gone.

So now the scrutiny and the accountability that you would be held at a more mature level is coming earlier in the cycle for companies. And I think that's what's driving CEOs to be okay month to month, quarter to quarter, where we stand, and that's why CFOs are more involved in the conversations and and there's good and bad that comes with that and i think but you're right you got uh i have it on my team now there's product marketers who are thinking okay what are we going to do you know what's our five-year three-year one-year plan like they've got that and we're working on that but we're like okay what are we doing for next quarter with this new gtm launch it that's next quarter's problem it's that's quarter well it actually needs to be this quarter's problem so so i think you so i've seen the same thing you're seeing is is the ceos are very focused on on what's right in front of them and not freed up to look longer down the path I think part of it is the funding cycles.

I think bootstrapped companies or older, more mature companies have some of that flexibility. So EZO is like, I'm going to call it a gray-haired startup. We're still innovating and launching new products and new solutions, but we've been around for like 16 years. so it we have the youthful energy and the vibrance of of a startup but it's got some maturity behind it it's got long-term planning and projects and and we have a strategic place where we want to take the platform five years from now and that does help like but that's because we're we're bootstrapped founder led bootstrapped company that doesn't have a vc going okay, I need my return on this investment, and you've got three years, and we now need to do our Series B and our C and our D and prepare for IPO or acquisitions.

And there's none of that distraction going on. So I think you get two different types of energy. One side when you PE or VC backed and you got many different it also depends on the there great VCs I worked with some wonderful value add VCs I'm not going to give them advertising, but I have worked with them. They know who they are.

And then I've worked with ones who are, they just are so, they're focused on what I would think is not what's best for the company, but they are doing what's best by their shareholders. But then I've worked with others who are phenomenal value-add and bring something more to the table than just money. And I think on the bootstrap side of things, I've worked with companies who have strategic leaders who can see down the road and see the value of building their brand and long-term incremental success and who are comfortable with that.

And then I've worked with others who are just, it's a lifestyle business for them. it's bootstrapped because they want to keep it small and simple. There's nothing wrong with that. So it's like you build what you want, you build what you love and everything needs to be a unicorn.

And so the marketing that you do and like how you make decisions to pitch strategy, all of that, that all comes from what style of leadership, like where the company wants to go based on the leader or the VCs. It does. You do kind of have to tailor your own, you know, your own path and your own way you pitch and thinking about the, it's kind of like the same thing you do with your, with a company does to their prospects is you got to find the unique value proposition that is going to help your audience meet their goals.

What keeps them up at night? What keeps my CEO up at night? What is going to be the measure of success for my company and my CEO and our board? What do they care about?

And that's what I need to go solve for. That's my job. My job is to make their lives easier and to find success for the greater organization, not just myself or my team or any Indian individual. At what point in your career did you come to that realization?

midway midway probably when i made that shift was within a company that was going preparing for its ipf very exciting time to be at a company and it was when i also was given a higher leadership role within so i'd gone from like a you know manager to now you're directing something and you've got a division and you've got a region and you've got PNL and you've got direct reports. And that was the shift. And you kind of got to see, be in those conversations and be in those meetings where you're having the conversations that I think your podcast focuses on is one of those conversations happening in boardrooms at that high executive level.

And then I saw, realized what type of filter was being put on it before it came, the messaging came down to the team. And I learned a big lesson there and I filter less. I don't filter a whole lot with my team. I was in a highly filtered situation there where I was like, whoa, there's a lot.

Like, this is not at all what the marching orders were being given. Uh-huh. And it was very eye-opening. And so I learned things that I liked, learned things that I wish I had been told, because you also have to look at how your people are.

Some people need to know the why. I think humans like to know the why. And they like, I think we also like, that's why we love stories so much. You get the why, you get closure, there's a conclusion, you get the tie-up.

that's why you hate cliffhangers that's why you hate the to be continued no i want to know why i want to know what happens next i want to know and i think it happens even in our professional life you know you're you're when you're in the trenches and you're you're hearing well why are we making this strategic decision why are we doing this and when that doesn't get answered people get confused and they draw their own conclusions and i learned that you don't want your team drawing their own conclusions.

You want to paint them the full picture as best you can because that will motivate them and drive them and help satisfy the why. Why are we doing this? Where is this leading? What's the purpose?

Why do you think that the higher-ups aren't sharing or why are they filtering so hard? I think it varies. At some companies, I've been in no-filter companies, complete transparency. And that's almost too much.

So I think you have to break balance. And I think in some companies, there is a heavy filter to either they're trying to protect their people and they think they just can't handle the pressure. And there was a lot of pressure preparing to go public. and the scrutiny, everything, and then the due diligence that was happening with the banking partners and everything.

There was a lot of questions that had to be answered. But I actually think had the team had some more visibility and understood, well, why do we have to change our reporting? Why are we changing this? Well, it's because we want to get to this greater place.

And I've worked at other places where they're very transparent. these are the things these are the check boxes these are the benchmarks we need to hit so we can go to our series B or our series C this is where our data needs to be this is the quality of our analytics and reporting that needs to be and those are the executive conversations like is our data room ready to open it up to investors can we answer hard questions can we play act you know okay hey poking holes okay explain that you know what are you going to do and how do you and that i actually found much more valuable and because then i do that exercise with my team and ask them okay so explain this you're doing the so when you prepared learned how to prepare for an IPO, you pulled those lessons into Ezio and your team now?

I do. I do Even though we not going for you know but it still that holding of accountability That level of accountability is was a different level than I seen before in my career And I thought they were good lessons. It's like, why do we wait? Why are we waiting for this level of due diligence and data analysis and accountability?

Why, why wait? Let's do that sooner. And then things do move smoother. There's something about sunlight on the whole process that is sanitizing and helpful.

What kind of things, for example, would a company at your current size without you not be looking at, but they would have to start looking at it if they're preparing for an IPO? it's that looking at spend analysis being very thoughtful about where the money is going and what it's being used for I think noticing leaks in the bucket and saying wait so it's not just about channel but campaigns and digging a little deeper into that and it's like you can identify waste it's eliminating waste and being more efficient and i think companies of all sizes and and structures could do better to exercise that so that's why i do like having cfos in the picture because they have that that mindset a lot of marketers don't they don't no and it's really hard to drill it down to that because a lot of them want to say that you can't put a money value on X and Y activity.

Yeah, exactly. How would you respond? Do you ever have people in your team trying to say that? And how do you, I mean, I guess not anymore because they know that you're going to ask them.

They've probably been trained from you, but how would you respond to that? I mean, I think one of those different strategies that I deploy with my team is, you know, I'm asking like how well do we know our customers the brand uh what's the buyer journey really like and one of the things we uncovered uh you know recently actually was you know we had mapped out and understand the buyer journey very very well for the u.s market we did not or did not know it for the international market in particular western europe uk uh you know western eu and i was like And that was a blind side.

I was like, why are those campaigns failing? Why is North America doing really well? Why is Latin America doing really well? What's going on there?

And really, we'd gotten, I don't know, lazy or whatever the blind side of it was, is applying the same logic and the same buyer journey analytics to Western Europe and the UK. and realizing we're just not buying or getting in front of the right eyeballs at the right stage and on the right platforms, and that it truly is different. And we went through kind of like a little scramble there to really do some good user interviews and figure out how they found us and where they are and learning more about them, that they are different and they're worth approaching uh their search for our types of solutions differently than the north american market uh or the latin american market even and and looking at that so first is what is your buyer journey and your your personas and not falling into the trap of one size fits all marketing um i think it you find success and And you kind of double down on that and you're like, all right, great.

Let's apply this everywhere. No, didn't work. So learn that and learn it fast and it's okay. And I think the other thing that you do when you're preparing for an IPO that you should be doing at all levels is thinking about your, your, the narrative of your, your, your company, your brand story.

and making sure that you're telling that brand story in a way that's compelling. And, of course, you're there. You're trying to make it compelling for investors, but you want to make it whatever resonates with them is going to resonate with a customer too. And I think there's still a lot of people who, when they are making a purchase, like a large enterprise software purchase or even one for a small mid-sized business, they they're building a relationship and they're buying into your story your narrative and making sure that you've got a compelling brand story like what are you doing for them uh it's really important to have that well understood and well well lined up so sales and customer success and everybody is telling that same unified story so it's consistent across the board is very key.

It's funny because I feel like that's something that everybody says you should do from the very beginning, but if nobody actually gets to it. It's a nice to have, not a need to have, I think in a lot of books. And really it should be done like you said. It should be done always.

I think everyone talks about it, but in the rush of doing, and this is like the real talk of marketing is there's things that should be done that just you only have so much time and expertise and and then you're busy making sure your your your trash can fires don't turn into dumpster fires they grow into house fires yeah oh god putting out all these little fires so they Don't become horrible, big, tragic events. All right. Well, that sounds like a good place to wrap it up. Rob, this has been a great conversation.

Thank you for sharing all of your insights and your journey with me today. Oh, absolutely a pleasure. Thank you for having me. And as always, for those who are watching or listening, feel free to connect with Rob on LinkedIn.

And if you enjoyed this episode, remember to share it with somebody. Let us know you watched it or listened to it and give it a like. and we will see you on the next one.