From Sales Rep to CEO: The Evolution of Leadership in SaaS Growth Stages

Introduction

Growing a SaaS company from startup to scale-up requires more than just a great product—it demands leadership that evolves as the company grows. In this enlightening conversation with Johnny Page, CEO of SaaS Academy, we explore the critical transformations founders must navigate as their companies reach different revenue milestones.

Johnny's journey from commission-only sales rep to CEO leading a multi-million dollar exit provides a compelling case study in adaptability and growth-focused leadership. Now helping over 500 SaaS founders scale their businesses through SaaS Academy, Johnny offers invaluable insights into the distinct growth stages of SaaS companies and how founder responsibilities must shift at each level.

This article explores the evolution of leadership across different SaaS growth stages, the common pitfalls that slow company growth, and how to identify the true bottlenecks preventing revenue expansion. Whether you're a founder wearing all the hats at an early-stage startup or a CEO looking to scale beyond $10 million in revenue, Johnny's experiences offer a roadmap for navigating the complex journey of SaaS growth.

The Evolution of Leadership Across SaaS Growth Stages

From Wearer of All Hats to True CEO

Johnny identifies distinct leadership transitions that founders must make as their companies grow:

"In the early days you're wearing all the hats... you're the product person, the delivery person, the sales person, the marketing person. From really early stages wearing every hat to now learning how to hire individual contributors, you become a manager for the first time."

This first transition—from doing everything yourself to managing individual contributors—represents a critical inflection point. According to Johnny, SaaS founders typically manage a team of individual contributors until reaching approximately $1 million in annual recurring revenue.

The next significant transition occurs between $1-3 million ARR:

"Generally speaking, at about a million in revenue, you start to hire your first level of leaders, and now the game changes again. The founder has to become exceptional at leading through leaders, and it's a totally different skill set."

This shift from managing individuals to leading leaders represents one of the most challenging adaptations for founders. Johnny explains why many struggle with this transition:

"It's not as satisfying on a daily basis when you are leading leaders as it was when you were the individual contributor. You used to go home every day and you'd be like you got a lot done, you could cross a lot of things off your to-do list."

The temptation to solve problems directly rather than developing leaders who can solve them creates a bottleneck:

"If you are the smartest person in the room, if you solve every problem that comes your way, that's not what leadership looks like. I've got to go build a leader that can make great decisions. If I jump in and tell them the answer, guess what happens the next time there's a problem? They come back to you, and now you just have higher overhead."

The final transition comes when the company reaches scale, typically beyond $10 million ARR:

"You step into your role as a CEO—it matches in title and in function—where you really are responsible for the vision and the alignment of your team around that vision."

At this stage, the CEO role becomes focused on three primary areas: vision, people, and cash. Everything else should be delegated to capable leaders within the organization.

Johnny's Personal Journey: From Sales Rep to CEO

Johnny's own career path perfectly illustrates these transitions. After abandoning his dream of playing professional golf, he joined a security company where he discovered a software product that would change his trajectory:

"I end up talking to the founders of this company and it turns out I'm one of their first five customers. They're like, 'We're going to hire a bunch of straight commission sales reps...you'll get 30% of the revenue.'"

Taking this risk—leaving a stable job for commission-only sales—became his defining "line in the sand" moment:

"Three years later I had sold over two million in annual recurring revenue on this, and I was getting 30% of it. I would go on to CEO that company... and lead them through a multi-million dollar exit."

What makes Johnny's story particularly noteworthy is that he never had ownership equity throughout most of this journey:

"I never [was an] owner in the company throughout the whole process, but the whole time I showed up as if I was."

This approach of taking full ownership of outcomes without actual ownership of the business allowed him to gain increasingly more responsibility and eventually leadership of the company.

Finding the True Bottleneck to SaaS Growth

The Three Revenue Levers in SaaS

According to Johnny, all SaaS growth challenges can be categorized into three areas:

"Every single challenge holding back revenue growth can be grouped into three different buckets. The first bucket is you can get more customers—your ability to acquire new users. The second bucket is your ability to keep them for longer—so retention. And the third one is how much are they worth to you."

These three levers—customer acquisition, retention, and monetization—represent the full spectrum of growth possibilities. The key to accelerating growth is identifying which of these areas truly represents the current bottleneck:

"To grow a business, you can either focus on getting more customers, keeping them for longer, or making them worth more."

The Danger of Working on the Wrong Problem

Many founders put tremendous effort into initiatives that don't address their actual bottleneck:

"Hard work and value creation are not directly correlated. There's no badge as a SaaS founder—no matter how gritty you are and how much you put up with—unless it's on the right problem, you don't grow."

Johnny provides a practical example:

"A podcast is not going to help a business grow if top-of-funnel awareness or lead generation is not the problem. If it's retention or monetization, it doesn't matter how much traffic we throw at the problem—the revenue is not going to move."

This insight explains why founders often feel stuck despite working extremely hard. The solution isn't necessarily working harder but working on the right problems:

"You could actually work a lot less and create a lot more growth when you learn how to find the bottleneck in the business. Even average execution on the right problem will unlock more revenue growth than world-class execution on the wrong problem."

The Most Overlooked Growth Lever: Pricing

Of the three growth levers, Johnny finds that pricing optimization is frequently neglected:

"A lot of people avoid the pricing conversation. They don't build the skills of monetizing their product or services or changing [prices], especially in a recurring revenue business model. I can't tell you how many people come to us and we ask them when was the last time you did a price increase, and they'll say three years ago."

Many founders avoid pricing conversations due to fear:

"There's a whole bunch of fears around that—will I turn customers out? My client's been loyal to us, I want to be loyal to them. There's a right way to have that conversation and to build that skill set."

By developing pricing as a skill rather than avoiding it, founders can often unlock substantial growth without needing to acquire a single new customer.

The Founder's Entrepreneurial Identity

Entrepreneur vs. CEO: Finding Your Lane

One of Johnny's most refreshing insights concerns the distinction between entrepreneurial spirit and the CEO role:

"I'm an entrepreneur at heart. I think that way—I don't make a very good employee. I'm going to have a very strong opinion, and I'm pretty obsessive over the things that I'm working on."

However, he challenges the notion that all founders must follow the same path:

"If you're listening and you are either in an organization or you're an entrepreneur and you're just not convinced about the product that you're building, the services you're building—go find someone else's that you are."

Johnny's experience demonstrates that entrepreneurial impact can happen even without being a founder:

"I felt like it was an incredible experience. Would I have loved to have been a founder and have equity at Silver Track? Of course. But man, I got to play in someone else's sandbox with zero risk, and I got the experience that came from that."

This experience allowed him to develop the skills to eventually negotiate for equity in his current role at SaaS Academy:

"I've learned how to have the conversation to say, 'Hey, I've earned trust through results.' I put a lot of points on the board for SaaS Academy before I ever had a conversation that said, 'If I'm going to keep on building this mission, I need to be able to build wealth through this.'"

Mission-Driven Performance

For Johnny, high performance isn't about achieving a standard model of success—it's about alignment with values and mission:

"High performance is not only about finding the right lane and the right skill set, background, and habits. If you're going to have longevity to performing well, performing above average, I think it comes down to working on the right project, for the right mission, you're on the right team, and it's really value-aligned for you."

This perspective helps explain how Johnny has been able to perform at such a high level throughout his career:

"I don't put constraints around what's my job or what's not—it's the mission. I'm getting plugged into: does this need to exist and more people need to hear about it? And then what's the role that I can play to contribute to that?"

His focus on mission over role has allowed him to expand his impact in each position:

"You earn more responsibility by performing well in the role that you're in."

Conclusion: Sequencing Equals Success

Johnny's journey from sales rep to CEO, and now to helping hundreds of SaaS founders scale their businesses, demonstrates the power of understanding business growth as a sequence of distinct stages, each requiring different leadership approaches.

The key insight for SaaS founders and leaders is to recognize that growth doesn't come from working harder on everything, but from working on the right things at the right time. As Johnny puts it: "Sequencing equals success."

This means understanding the current bottleneck in your business—whether it's customer acquisition, retention, or monetization—and focusing your efforts there. It also means developing as a leader through the different stages of company growth, from wearing all the hats to leading through leaders and ultimately focusing on vision and alignment.

By understanding these transitions and focusing on the right problems at the right time, SaaS founders can achieve growth with less effort and move closer to what Johnny calls "the perfect exit"—the point at which founders have created enough value to have options, whether that means selling the business or hiring an executive team to run it.

As Johnny summarizes his mission at SaaS Academy: "Our mission is to help SaaS founders achieve their perfect exit. That means they've gotten to a point in the business where they have choices now."

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