Scale Like a CEO

Scale Like a CEO: Transitioning to SaaS & Building Leadership Culture with Dean Curtis

• Justin Reinert • Season 1 • Episode 61

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Most decks drain attention; the best stories drive decisions. We sit down with Dean Curtis, CEO of Ingage, to unpack how a services agency transformed into a focused SaaS company by turning sales content into interactive, data-driven experiences that prospects actually remember. Dean shares the messy middle of building go-to-market while the product was still taking shape, the moment they chose a single vertical in home services, and the downstream effects of that decision on retention, revenue quality, and roadmap discipline.

We get tactical about leadership. Dean explains how stepping from CRO/COO into the CEO role forced him to stop being the doer and start building the people who build the business. He walks through hiring for curiosity and ownership over resume length, replacing leaders as growth ceilings changed, and anchoring culture on two simple values: customer first and value focused. The conversation gets real on feedback: how he rebuilt one-on-ones around the employee’s agenda, required unfiltered two-way critique, and learned to ask clarifying questions instead of shutting ideas down. Psychological safety didn’t appear overnight; consistency and grace made it stick.

Alignment is a system, not a slogan. Dean outlines the OKR backbone, quarterly onsite planning, monthly business reviews, and a candid weekly update video that surfaces wins and misses across teams. He also breaks down the 1080-10 leadership framework: set the first 10% with a clear definition of done, empower the team to own the middle 80%, then return for the final 10% to raise the standard. It’s a practical playbook for SaaS founders and operators who want product market fit, accountable teams, and a culture that scales.

If this conversation gave you a useful tactic or a new lens on leadership, follow the show, share it with a teammate, and leave a quick review so others can find it. Got a PMF story or a feedback ritual that works? Send us a note—we’d love to hear it.

SPEAKER_00:

Welcome to the Scale Like a CEO podcast with your host, Justin. In today's episode, we're joined by Dean Curtis, CEO of Engage. Dean shares his journey transitioning from a digital agency to a SaaS company, discussing the challenges of finding product market fit and building a strong leadership culture.

Justin:

Dean, thanks so much for joining me on the Scale Like a CEO podcast. To get us started, if you wouldn't mind, give us a 90-second intro to you and your business.

SPEAKER_02:

Yeah, Justin, thanks so much for having me. I really appreciate it. Yeah, so at Engage, we help teams deliver more compelling sales content. So we do that through interactive data-driven storytelling. The Engage platform really lets businesses move beyond static, normal, boring decks and create experiences that help keep audiences engaged. A little bit of a play on words. I got into this because I saw how hard it was for teams to communicate ideas that stick when they're communicating with their prospects. And we wanted to make a great storytelling tool that's accessible to every business, not just those with complex high-end design teams. So today we primarily work with her home services companies. So think exterior remodelers or people who might come to your home to do something. And we want to help them turn information into stories that drive action.

Justin:

Great. And you've been with Engage for nine years. Is that right? Nine years. Yeah. Yeah. And so you started off in roles other than the CEO, but then became the CEO about six years ago. Tell me a little bit about that transition and things that you had to shift as you stepped into that role of CEO.

SPEAKER_02:

Yeah, absolutely. It was a journey for sure. When I started here, the whole remit of why myself and another gentleman were brought in was to transition the company from what was a digital agency into a pure software company. And that took obviously a little bit of time. You don't make that transition overnight. So when I was brought in, I was really focused on the go-to-market for the new software platform. Well, it's kind of hard to do that as you're building it, right? It's kind of like changing the tires on a car as it's rolling down the road. So it was a few years where I was in that CRO, COO spot. And then as the business changed, the CEO left, and I was the next logical person to step in. And at that point, we had built the software that we had intended to build. And we were trying to find product market fit. And as any SaaS founder will tell you, that is one of the hardest things to do, is to really, you think it could be for everyone, but if your product is for everyone, it's probably for no one until you know it's for actually someone. Figure that circular reasoning out. But it's true, you have to find someone who really likes it. And we found this home improvement vertical. And as I stepped into the CEO role, I said, listen, we know we have a good amount of customers that are using it in this use case. Let's focus on that. And that's what we did when I became the CEO six years ago now.

Justin:

Yeah. Well, that's great. And we picked up that role of CEO. What were some things that you had to let go of and some things that you had to pick up as you kind of transitioned into that role?

SPEAKER_02:

Yeah, I think one of the hardest things is I'm a doer by nature. So I had to really understand what my skills were and where my gaps were and where the team could really pick up the slack. And I think at every growth ceiling that we hit along the way, that changed as well. So as I let go of some things, I had to pick up other things. As a leader proved that they weren't the right person and I had to replace them, I maybe had to step back into that role. And I think at all different points along the journey, that's just what you have to do as the ultimate leader of the company. And I don't say that in a self-serving way. It's just that's how it works. And sometimes stepping back into a role in order to better understand how things are going and how you can maybe improve it is a great way to go. I think as I go in the seat now, it's really about building the people so that I'm not doing everything. That's the biggest shift.

Justin:

Yeah, for sure. For sure. Being able to get the right people around you to be able to continue growing the business. I'm curious, as you shifted the business model from a service to more of a SaaS play, what changed in what you needed from your leaders, or if anything was a whole new leadership team.

SPEAKER_02:

So we had to really think through the I and I think this is not a dean phrase. I'm sure other people have said this. What got us here won't get us there. It's a very common thing in business. We really had to look at the skill sets to say, well, we had a bunch of people who were really good in the agency world. Are they still the right leaders to take us forward in this software realm? And we found that that wasn't the case, that we just needed people who had that experience. So we made those changes as was necessary to get us the right team in order to execute the plan that we had.

Justin:

And so what were some of the qualities that you were looking for those people on that team?

SPEAKER_02:

So I've always had a very aspirational bend in my hiring practices. So I was always looking for people who had the curiosity, but maybe not always the experience, right? Because as you're building a software company or building any company, cash is king. You need to make sure your cash is gonna get you there. So sometimes you can't afford to spend for the seasoned veteran who's done it for 25 years, but also sometimes that seasoned veteran who's done it for 25 years doesn't necessarily have the energy to continue doing it in a new environment, in a new startup. So the qualities I was looking for are people who would quickly roll up their sleeves and get to work, who would not just bring me problems and lay them on my desk, but take ownership over that. Right. And that has shaped the core values that we live by, being customer first, being value focused, so that I know they're taking their time to first put the customer in the lead. And second, look at the value of what they're doing and how it returns value to the company. So those are the two big things that I looked for.

Justin:

And so as you've grown over the past years, have there been any moments where your growth led to a need for structure change?

SPEAKER_02:

Oh, yeah, constantly. I mean, I think as you go through each of the growth phases, right, you go from no revenue to a million to three million to five to ten. Every step requires a relook at how you're structured to make sure you have the right leaders in place who are building the business alongside of you. As the CEO, I cannot be in all those places at once. And I need leaders that I can trust along the way. So making sure that I'm building the people who are then building the business, it probably sounds repetitive, but that's the plan. That's the way we always think about it. And you have to adjust. It just happens to be that each growth ceiling presents its own set of challenges, therefore, it's going to present its own need for different skills.

Justin:

I really like that you've got this focus on building the people that will build the business. Tell me, what specifically are you doing to build the people?

SPEAKER_02:

Yeah, I think the big thing that I've done, especially recently, probably in the last six months, is I completely flipped our one-on-one structure. So I'm a firm believer that spending time with each team member that directly reports to me every week, it's some of the most valuable time that I can spend. I the way I organize that time, though, it's all based on what that team member needs. It's not my list, it's their list. And the one thing that I added at the bottom of every single one-on-one is a feedback section. And we are both required to give each other feedback from the previous week: positive, negative, unfiltered feedback so that we can improve. And I think that is the number one thing is having that open line of communication between me and the direct report in order to know that one, I'm in their corner. And two, they can provide me feedback where I might have fallen short and I'm willing to take it. The only thing I'm allowed to say is thank you, or can you please clarify? And then the opposite is true as well. We want to make sure we have that open line of communication.

Justin:

I love that you've got a feedback mechanism that also requires a thank you and no judgment on the feedback. I think that's so critical. I would imagine, though, getting that started could be challenging to have the right level of psych safety and that people are just comfortable the first time that Dean's saying, Hey, give me feedback, that they're ready to give you some candid feedback. So tell me a little bit about how you got them comfortable.

SPEAKER_02:

Yeah, I would say it's always a work in progress. I think as we've implemented it, it's definitely taken some time. There's a lot of softballs at the beginning. Oh, I really like how you did this. Oh, I really no, I want to hear it. I want to hear where I fell short. I think as you're in a leadership position too, people are afraid to tell you. They want to be nice. They don't want to look like they're being critical. They may not have the confidence. And my caution is you have to do it. You need to take a little step at a time and say, Well, we're not leaving the meeting until you give me some feedback. I'm not perfect. I know there's things that I can improve on. And at the beginning, I did have a ton of grace, and I still do. We have a week where it's just been a good week. It's okay, it's no big deal. Well, I'm happy to let it slide, but it can't slide for more than one.

Justin:

Yeah, I'm curious if you wouldn't mind being so vulnerable. What's some of the toughest feedback that you've received in some of those cycles? Oh man.

SPEAKER_02:

Where do I start? I would say the first one is hey, you do you remember this meeting this week? You really shut me down. You didn't give me an opportunity to speak. Like, oh man, such a tough thing to hear. But fair. Hey, you jumped over me, or I had an idea. And I think one of the biggest things that I try to do as a leader is to ask questions rather than make statements. And sometimes when someone brings an idea and you shut them down right away, you don't really truly understand what maybe their point was. So to ask that clarifying question could have prevented that entire situation of someone feeling shut down or unheard. So to me, that's a real one that happened. And I have to admit, it's happened more than once, where I need to get better as a leader to think and ask that question first rather than making the assumption that I understand what they're saying.

Justin:

Yeah. Well, it sounds like your people are able to give effective feedback because they're positioning it in hey, there's this specific situation, and here's specifically the behavior that I observed. So it sounds like you're doing a great job with building that feedback culture. I'm curious, I would imagine that over this transition and then growing into this new software company, that there's been a lot of shifts. And I'm curious how you have maintained alignment as you've continued to grow. Yeah.

SPEAKER_02:

So what's interesting is we're in the middle of it this week. I literally stepped out of our quarterly planning session in order to come and record with you today. A big part of our alignment is our meeting rhythm. So we have a very strict meeting rhythm, and I shouldn't say strict, but very consistent meeting rhythm within the company. So we have quarterly meetings where our entire leadership team comes to our office in Pennsylvania where we sit and spend three days talking about the quarter, how it's gone so far. We do this about halfway through the quarter. Uh, and then what our plans are for the next quarter. And obviously, during here in quarter four, we're planning for the strategic plan for 2026. We look at how well we've done against the objectives that we've set. We use the OKR model. So are we on target for that objective? Are we marching in the right direction for all of our key results? Do all the team members have initiatives? So we use that OKR model. We have a very consistent meeting cadence of quarterly sprint planning, monthly business reviews, and then weekly team meetings with very structured agendas to ensure we're focused on the things that matter. And we do something as simple as each week I record a weekly update for the company. And it's a quick 10 to 15 minute video. And in that video, I don't write the script. The team writes the script and sends it to me. And then I tell the whole rest of the team what's going on, what progress we're making against our goals. It's not just a bunch of feel-good stuff either. It's, hey, we had this really tough situation with a customer last week, or the sales team didn't hit their number, or the we had a really tough support issue. So it's it's the good and the bad in order to stay connected as a team. So lots of ways that we're trying to stay aligned from weekly updates to consistent meeting rhythms that really help us really to commit to each other, but also execute the plans that we set in place.

Justin:

That constant communication loop is so critical in maintaining alignment. So it sounds like you're doing an amazing job with a lot of people. I'd like to I'd like to think we're doing pretty good.

SPEAKER_02:

I don't know if amazing is quite there yet, but a little bit better this year than we were last year, a little bit better this quarter than we were last quarter. Just consistently making progress is all we can ask for.

Justin:

Yeah, well, that's so great. So as you look into the future, how do you define the leadership culture that you want to kind of continue to drive into the next five or 10 years?

SPEAKER_02:

Yeah, I want to ensure that I'm building the leaders who can then build their part of our business. I don't think of our company as departments, I think of them as teams. So as I'm the coach of the coaches, I want to make sure that I'm building my team so that they can then enable their team to do the best work that they can do. So we the principle that I use is what I call the 1080-10 principle. So I want to help people get the first 10% of a project started, but 80% should be done by the people who need to actually own it in the business. I shouldn't be working in the business all the time. I want to give them the direction. I want to help them understand the definition of done and then let them go. Now, if if they fail or if they struggle along the way, I'm always going to be there to help support them. And I want my leaders to be there to support their team. But if we're not empowering the people who are doing the work every single day to have ownership over that work, we might as well do it ourselves. So to me, the leadership framework that we want to live by is that 1080-10 principle. I'll come in and help you at the end with the last 10% so we can make it great. But 80% needs to be owned by someone else. Because if we as leaders are owning that 80%, we're never going to get where we need to go.

Justin:

Yeah, that's great. And so if somebody joined your company tomorrow, what would you want them to say about your leadership in five years?

SPEAKER_02:

Man. I'm going to take it from the opposite perspective. There's great opportunity for people in the market. And I don't expect that our company is going to be everyone's last job. And I would say when they leave and go somewhere else, that they use the things that they've learned here as the new standard for whatever they're going to do next. Where they it's always annoying when that person comes in your company and is like, well, at my old company, we did it this way. But I do want people to take things from what we've taught them and what they've learned here to say, hey, I have a way that we did it previously that might be a good way to operate. Or I remember fondly the time that I spent at Engage because of the leadership style and them allowing me to really own the things that I work on, fail a little bit, make mistakes, and learn from those rather than a command and control culture. So to me, I look at it from down the road when I run into somebody at the local cafe and they've gone on to somewhere else and they come back and they say to me, Boy, I really learned this thing when I was at your company and I was able to go and do great things because of it. That to me would be the ultimate reward.

Justin:

Yeah, that's always incredible when you get that. I can think of times in my career when I run into someone that I was with five, 10, 15 years ago, and they're like, Man, there's this one thing that I learned from you that I still use today. And there's nothing better than that. Yeah, so good. Well, Dean, I've really enjoyed the conversation today. And thank you for for your time. If folks want to get in touch with you, what's the best way to do so?

SPEAKER_02:

Yeah, if you're interested in what we do here at Engage, our website is engage.io. Engage is with an I, so I-N-G-A-G-E.io. For me personally, I spend probably a little bit too much time on Instagram. You could connect with me, DeanCurtis23 on Instagram. Not only personal stuff, but lots of business stuff on there as well. My thoughts on leadership, things that we're doing in the market, great place to connect with me personally. And just send me a message that says Justin, and then I'll know that you came from this podcast.

Justin:

I love that. Well, Dean, thank you so much again for your time today. Thanks, Justin. I appreciate your time too.