Five Strategies for Success as a Chief Revenue Officer

In the fast-paced world of technology companies, the role of Chief Revenue Officer (CRO) holds immense importance for growth and success. Drawing from my experience as the former CRO of Datadog, one of New York’s most successful tech IPOs, below are five valuable insights on how to excel in this position.

1. Seek Alignment with the CEO

Establishing a mutually agreed upon mission and understanding of success is pivotal. At Datadog, listening to the CEO’s vision for the CRO role helped me create a plan to achieve those objectives, get an agreement and ensure the team’s support for that plan. We maintained open lines of communication and shared ideas regularly to ensure continuous alignment.

One of the hardest parts of the job is when the CRO’s vision is different from the CEO’s vision. These conversations can get heated, so the CRO must seek to understand before seeking to be understood. Then they can present their case and concerns. It is best to be objective, limit emotions and be intellectually- honest to find the best answers, as well as acknowledging concerns, staying focused on progress, and being ready to course-correct. By following a process of deep listening, showing mutual respect, collaborating on new methods and reviewing results, we grew from $60M annual recurring revenue (ARR) to $1B ARR in four and a half years.

2. Never Stop Recruiting

A leader is only as good as their team and their team is only as good as they can recruit. The CRO must make sure they are constantly recruiting top talent, and that their leaders are also capable of recruiting A-players. A-players are those who are going to figure out how to win deals, how to improve sales processes, how to improve messaging, and they’re going to attract other A-players. Even when there are not any or very few open headcount spots, the CRO should be recruiting. There will also be opportunities to promote talented employees already at the company. An employee might unexpectedly leave their company, creating an opening to either promote or hire top talent. In these situations, the CRO should not be caught flat-footed. Having a good pipeline of top talent ready to come on board is important. Also, A-players don’t want to work with C- and B-players. They want to work with other top players. At Datadog, recruiting incredible people and helping the leaders on my team recruit incredible people had the biggest impact on my ability to succeed in the CRO role.

3. Build Strong C-suite Alignment

Collaboration and trust between C-suite and the rest of the organization is vital for success in sales. Legal, HR, product, engineering and marketing teams must be aligned and passionately working toward shared objectives. Building strong relationships and effectively communicating the “why?” behind our actions fosters cohesive progress towards our collective goals.

A CRO can build a high level of trust by taking the time to get to know each department head personally, understand what motivates them and vice versa. A mistake some leaders make is viewing only their department as their team and all other departments as adversaries. Patrick Lencioni refers to a “First Team” as all the leaders at the same level, which for the CRO is the other C-suite leaders and believes those leaders must prioritize each other before the employees that they each manage. The investment I made in connecting with other leaders throughout the company paid off. We pushed through challenging levels of growth together and were allies helping the company grow into a new, larger faster-moving entity.

4. Exemplify Sales Fundamentals

Sales fundamentals must be at the heart of the CRO role. Leading by example inspires dedication and commitment within the team and promotes a culture that amplifies and replicates the examples they set. If the CRO wants their team to meet with customers, then they need to meet with customers. If the CRO want people to have mastery of the messaging, then they must deliver a compelling pitch. If a CRO wants their salespeople to consistently drive pipeline generation, then they should show them how to cold call to create new opportunities. There is an old saying, “Do what I say, not what I do,” which doesn’t work with children, nor does it work in leadership.

I’ve worked for the leader who “yells at the scoreboard” telling everybody what they should do but has not shown that they can do it themselves. Don’t be that person. At Medallia and Datadog, I averaged 150,000 airline miles per year and met with as many customers and teammates as possible. I relentlessly scoured the forecast every week, digging into deals with teams. I helped create and lead weekly, monthly and quarterly training courses on product knowledge, messaging, sales process, and competition based on my own experience with the team in the field. When a sales team knows the CRO is with them, and the CRO asks their team to accomplish the impossible, they will follow and make it happen.

It’s important to stay true to these fundamentals even if others say it won’t work. Until the new fundamentals kick in and start working, it can look like they won’t work and there will be temptation to abandon them. For example, I pushed outbound cold calling at Datadog. Initial results didn’t look good. I dug in and found a number of the team didn’t want it to work, so they weren’t trying. The junior team members, however, were willing to do the cold outreach and got results. They proved the approach worked and we were able to successfully roll it out across the company.

5. Optimize Team Performance

Creating the sense of being part of something exceptional and inspiring the team to believe in the company’s mission and vision is a powerful motivator. In addition, establishing a safe and collaborative learning environment, where experiences—triumphs and setbacks—are openly shared, encourages growth and learning. This, and maintaining an atmosphere of empathy and respect for each individual’s journey, propels the team to achieve extraordinary results.

During the first meeting I had with the team at Datadog, I told them we would double revenue over the next two years, have a multi-billion-dollar IPO, that they would learn more on our team than anywhere else, make life-changing money and never have to look for a job again because they would be known for their spectacular success. People had their arms crossed, some openly smirked and I got in a bit of trouble with the CEO for making these crazy claims. However, there were some team members who had a gleam in their eyes and wanted to believe me. It was the first step in getting them to believe this could be one of the most special experiences of their lives. I said it every day and worked to achieve the victories that made them believe it could be true.

The next step was to create a safe space for learning, where they could share failures and successes. It was easy to lead by example, since I had a lot to learn about this new company and space, too. I made reviews of calls, emails and client meet-ups a key part of weekly global sales meetings. We shared emails, presentations, techniques and created an atmosphere of shared learning.

This was helpful in drawing in the junior team and shy people who might not feel comfortable having a voice in the larger group or in front of more senior people. We received a ton of valuable knowledge from reps who were a year or two out of university, but who were trying new approaches and having successes we could learn from.

Incorporating these five strategies and insights as CRO can guide them toward fostering a collaborative, dedicated and strategically aligned team, propelled toward collective success. If it can happen for me–it can happen for any CRO.