The sales leadership to CEO career path
Let me share my perspective on the transition from Chief Revenue Officer (CRO) to CEO, and why I think it's not the most challenging career step in sales leadership.
I believe the toughest transition is actually moving from Head of North American Sales to CRO – not from CRO to CEO.
Why jumping from sales leadership to CRO is so difficult
Think about the typical sales career path: you might start as an SDR or inside sales rep, doing the hunting. If you're successful, you move up to account management or frontline sales.
Keep performing well, and you'll progress to frontline manager, then regional manager, and eventually director.
Throughout this journey, you're laser-focused on one thing: managing the forecast, driving activity, closing deals, MEDDPICC, and starting fresh each quarter with new targets.
It's very one-dimensional – it's all about that hustle and drive to hit your numbers.
When you're heading North American sales, you're still operating in that same rhythm: drive activity, maintain pipeline momentum, close deals, and repeat. The metrics and methods are deeply ingrained – you're living and breathing that sales cycle mentality.
You might be managing frontline sellers bringing in new business excellently, but stepping into the CRO role introduces whole new dimensions.
Suddenly, you're overseeing customer success, which is a completely different animal, and channel business, which many sales leaders initially undervalue. You also inherit solutions architects and this thing called “RevOps” that handles all the systems and automation you probably disliked as a frontline seller.
Now, you're making decisions about the entire revenue infrastructure – choosing methodologies, implementing them in Salesforce or other tools, and managing finance, HR, and legal negotiations.
The focus shifts from just winning deals to driving overall recurring revenue. You start to realize that customer success actually handles more of the business than those frontline sellers you used to think were everything.
Rebecca Stewart
Moving from CRO to CEO
As CRO, you don't need to be an expert in every function, but you need to deeply understand their value.
You have to create systems, structures, and processes while carefully balancing resources across teams. Success comes from finding talented leaders who are passionate about their specific areas (whether that's channel partnerships, customer success, or RevOps) and aligning their strategies.
Eventually, you become tightly connected with the product organization, constantly feeding back customer needs, competitive insights, and pricing considerations. You partner closely with the Chief Product Officer and engineering team to keep innovating.
Moving from CRO to CEO isn't actually that big of a leap - you're mainly adding product and engineering to your portfolio. If you've been a CRO, you're already handling HR, legal, and marketing (or working closely with them).
The main new challenges are things like shareholder relations, earnings calls, and regulatory compliance – but these are learnable skills, especially with the right team around you.
The CRO-to-CEO transition makes sense when a company needs someone to scale an existing successful product.
Andrew Ettinger
How to prepare sales leaders for the CRO role
To successfully move up in leadership, it's crucial to understand and embrace the different functions within a company. The key is being curious and moving beyond a one-dimensional focus.
The leaders who make that leap successfully are the ones who've built strong relationships across departments throughout their careers.
For example, at ThousandEyes, our best enterprise leaders worked closely with customer success teams. They understood that creating a "pod" structure – combining frontline sales, customer success, and technical support – was incredibly powerful.
Even though these leaders didn't directly manage the solutions architects or customer success teams, they became what you might call "subscribe to" leaders rather than traditional command-and-control managers.
They'd guide the entire pod by bringing customer success and solutions architects along on the journey, especially when handling complex enterprise customers where you need to coordinate multiple moving parts.
This kind of collaborative leadership style is particularly effective when you're dealing with complex enterprise customers that require coordinating multiple components. Instead of just giving orders, these leaders excel at bringing different teams together toward a common goal.
Daniel O’Dowd
Recognizing leadership potential
Sometimes, it's important to recognize that not everyone wants to climb the leadership ladder.
Many of our best sales professionals are frontline sellers who are completely content in that role - and that's fantastic. Some of them will happily retire as top performers, making great money and having no desire to move into management.
The key is identifying people who naturally want to progress beyond being individual contributors. These folks show genuine interest in leadership and are open to learning and growing.
That's a much easier path to develop than trying to force someone into a role they don't want.
I experienced this myself. I was crushing it in frontline sales when a senior leader I respected pulled me aside and said, "You know you've got more to offer than this. You've proven you can excel here over and over - it's time to step into leadership."
That conversation was a real turning point for me.
If you'd asked me a year or two before that, I would've told you being an enterprise seller was the greatest job in the world and I'd never leave it.
But sometimes, people see potential in you that you don't see in yourself, and that push can energize you to take the next step.
Ella Harrison
The power of becoming a mentor
The most successful leaders are often those who've not only proven themselves individually, but who also naturally gravitate toward coaching and mentoring younger talent.
There's this pivotal moment that happens – you realize you're getting more excited about your mentee's success than your own. That's when you know you're ready for leadership.
It's a much better indicator than simply feeling like you've hit a ceiling as a seller and need to move up.
True leadership potential shows itself when you've already proven your own abilities, but find yourself naturally drawn to helping others succeed. When their wins become your wins - that's the real sign you're ready to step into a leadership role.
Angelique Kamara
Thinking beyond just selling
One of the interesting contradictions in sales is how we compensate people: we reward individual performance rather than teamwork, essentially discouraging collaboration.
When you look at commission structures, there's often no financial benefit for helping your colleagues succeed – in fact, it might even work against you.
But here's what's fascinating: in SaaS businesses, one of the earliest signs of a potential leader is when someone starts caring about adoption, even though they're not compensated for it.
Think about annual recurring revenue (ARR); everyone's paid to bring it in, but that first 'R' – recurring – is crucial. Without actual adoption, it's just temporary revenue. It's like a gym membership - if you don't use it, you're probably not going to keep paying for it.
The sales reps who stand out are the ones who care about whether their customers are actually using the product, even though that's technically the customer success team's job.
These people understand the bigger picture: if customers don't adopt the product, they won't renew. Without renewals, the business can't build a healthy recurring revenue model.
This kind of three-dimensional thinking – understanding how your individual sales connect to adoption, which leads to recurring revenue, which drives business growth – is what sets potential leaders apart.
They see beyond the immediate commission check to how their work impacts the entire business ecosystem.
Ella Harrison
Final thoughts
To conclude, to become a great CRO, you’ve got to have the hunger and drive, because they're not easy roles. You need to have a relentless drive to understand each part of the functions you're leading and ensure you're winning in each space.
It takes a huge amount of time and energy, but it’s worth it.
