Navigating the Transition from CRO to CEO

Congratulations! You’ve just landed the coveted role of CEO, a position that comes with its own set of challenges and rewards. As a group of venture capital GP’s who are also former CEOs, we have been in your shoes. We have also had the privilege of training numerous CEOs and we understand the unique journey you’re about to embark on.

Transitioning from Chief Revenue Officer (CRO) to CEO is a significant leap, one that requires a shift in mindset, responsibilities, and leadership style. At Grit Capital Partners, we see this CRO/CEO transition as unique. It is different from CEO’s coming from product, technology, finance or operations. This transition can happen either because you are founding a new company, or because you have been recruited to take over. Either way,  with the right mindset, you can navigate this transition successfully.  

First and foremost, let’s address the elephant in the room: the shift from being focused on revenue generation to overseeing the entire organization. As a CRO, your primary goal was likely to drive sales and revenue growth. While revenue generation remains crucial as a CEO, your role now encompasses much more than just sales. You’re responsible for setting the overall vision and strategy, raising capital, managing operations, fostering company culture, and ensuring long-term sustainability. It’s a broader scope that requires a strategic approach and a big-picture mindset.

One of the biggest challenges you’ll face is learning to delegate effectively. As a CRO, you may have been used to being hands-on and directly involved in sales activities. However, as CEO, you simply can’t do it all yourself. And if you try, you will indeed have some success that is almost always regretted later as it becomes understood in the rearview mirror as unscalable and distracting. In the sample set seen over my career, you will have much quicker success as a new CEO if you immediately appoint a head of sales or revenue. You need to trust your team and empower them to take ownership of their roles. Delegation doesn’t mean relinquishing control entirely; rather, it’s about finding the right balance between oversight and autonomy. Remember, you hired talented individuals for a reason, so let them deliver for you, in a way which is almost always – not exactly like you would. 

Communication is another key aspect of your new role. As CEO, you’ll need to communicate your vision and strategy clearly and consistently to all stakeholders, including employees, investors, customers, and partners. Effective communication fosters alignment and ensures that everyone is working towards the same goals. Don’t underestimate the power of transparency and honesty. Keep your team informed about the company’s progress, challenges, and successes. Open communication builds trust and encourages collaboration. 

Another piece of communication that requires transition is with your board. By this time in your career, as a CRO, you will have likely attended many board meetings and presented your piece at most of them.  In that situation, you are reporting out and giving color on why results manifested the way they did.  You give credit to team members, describing market dynamics during the previous quarter, etc. If a board member asked you what you think, you gave them a measuredly optimistic answer, being sure to stay in the assigned lane.   

The most difficult transition I typically see is the new CEO understanding that the board needs leadership as well as the team.  The dialogue is no longer just a report out, and color on what has occurred in the prior period.  When asked (and of course when not asked – more importantly), your opinion, optimism, realism, about the future matters. Beyond this, and importantly, what you can envision matters. From the newest transitioning CROs, you rarely hear the words “here’s what I see”.  Beyond your team, the board, investors, and all stakeholders need you to navigate the ship and tell them where it is headed. 

Leading by example is also essential for any CEO. Your actions and behaviors set the tone for the entire organization. As a former CRO, you’re no stranger to hard work and dedication, but now you’ll need to demonstrate leadership qualities that inspire and motivate others. Be authentic, approachable, and empathetic. Show genuine interest in your team members’ professional development and well-being. A strong company culture starts at the top, so lead with integrity and positivity.

Another critical aspect of your role as CEO is strategic decision-making. While as a CRO, you may have been focused on short-term sales targets, as CEO, you must take a more long-term view. You’ll need to evaluate various opportunities and risks, weigh the pros and cons, and make decisions that align with the company’s overall goals and values. It’s okay to seek input from your team and advisors, but ultimately, the buck stops with you. Embrace the responsibility that comes with being the ultimate decision-maker.

As you settle into your new role, don’t forget to invest in your own growth and development. The transition from CRO to CEO is a learning process, and there will be challenges along the way. Seek out mentors, coaches, and peers who can offer guidance and support. Take advantage of training programs, workshops, and networking opportunities. Remember, even the most seasoned CEOs are constantly learning and evolving.

Outside voices are critical. Don’t be afraid to ask for help when you need it. Leading a company is a lonely thing, but you’re not in it alone. Lean on your team, advisors, and fellow CEOs for advice and support. Building a strong support network is crucial for success in the top job.

Rosie O’Meara, CEO at Ground Truth and one of my favorite examples of this successful transition, shares her insights on this topic:

The most common paths to CEO in our industry are those from being a Founder, COO, CFO, and CRO. There are benefits to each “type” of CEO, but for a former CRO, a deep understanding of the market and customers is a superpower. I have learned to lean into that and to use it to develop a customer-centric strategy and vision. I delegate to and partner with a great CFO on the heavier finance responsibilities, because that’s not yet my strength. I’m open about my gaps and I focus on applying what I’m best at to the needs of the business. If I didn’t have a really great CFO, I would get one.   

Reorienting my time has been a big shift. My time should now be spent less on things that get us to this year’s goals, and more on things that create longer term outcomes for the company. It’s really tempting as a former CRO to want to roll up my sleeves and go back to selling, but that’s not what the company needs from me. When I do work directly with customers (which will always be my favorite use of time), the conversations are that much more strategically interesting and oriented toward both of our longer term goals.  

Seeing my name shift in our org chart from Revenue to G&A was an unexpectedly deflating moment – in sales and revenue roles, I had gotten so used to having very specific goals tied to numbers, and a really clear way to measure success and failure. Success is measured differently in this role, and there is often a longer tail on seeing and understanding the impact of decisions and efforts. On the other hand, I now have the ability to design and impact the overall company systems that ultimately support revenue growth. What sales leader hasn’t dreamed of the changes they would make if they could? Viewing this as an opportunity allows me to focus on high-level strategy that may be less directly tied to revenue, but with the mindset that growth is still the desired outcome in everything we do.

In conclusion, transitioning from CRO to CEO is a significant career milestone that comes with its own set of challenges and opportunities. The greatest way to show up in this role is humble and ambitious. “Humbitious” is what we say at Grit Capital Partners, and we are looking for this in the leaders we back. With the right mindset and approach, you can thrive as a CEO and lead your company to new heights. Best of luck on your journey!