For CEOs

How to Engage With Your CRO

Post 4 of 4 in the Startup Series for CRO’s.

Assuming your CRO is on track and scaling with the company so that you’re not having to mentor or coach them, I’ve found a few ways to engage with the CRO that have been particularly fruitful. Here are a few tips on making every moment with your CRO well-spent.

One of the easiest ways to carve out quality time with your CRO is during travel time, or in and around events. Particularly if you’re a B2B company that engages with clients during the sales process, you’ll probably find yourself at a lot of client meetings and events, either internal or external. Your CRO will be there, too, which gives you a great opportunity to spend large blocks of time together in transit, or a good deal of time together socially. One thing we learned during the work-at-home pandemic is just how much time we save by not traveling. So when life returns to normal, why waste time in an Uber or on a plane when you can have a deep strategic conversation or even a personal/social one with one of your senior executives? Of course, you have to actually be more proactive in meeting with your CRO since you won’t have events that naturally bring you together, but I’ve found that the early morning time in the hotel gym or late-night drink in the lobby bar before heading up to bed now translates to time I can have with my CRO.

Another way to engage with the CRO is in a Weekly Forecast meeting. Jeff Epstein, former CFO of Oracle, was one of my long-time board members at Return Path and he helped us architect a new core business process once our sales team got large and mature and geographically disparate enough that it was hard for us to have a solid forecast. Both me and our CFO engaged in the Weekly Forecast meeting and because of that we forced the discipline of a good roll-up of all regions and business units. The CRO and all sales managers attended and knew that we were paying attention to the numbers and trends and asking tough questions. Our attendance was a forcing function for the CRO so that they organized a pre-meeting the prior day with all teams and units to prepare, and that in and of itself had a cascading effect through the organization of adding discipline, rigor, and accuracy to the forecast. It also made me a lot more empathetic to my CRO’s issues with respect to the sales leadership team.

Finally, the other way that I engaged with the CRO was ad hoc, either internally or in-market. My most successful heads of sales have been good at winding me up and pointing me at things as needed, whether that means getting on a plane or Zoom to help close a deal or save a client, or doing a 1:1 mentoring session with a key employee. So, not all interactions with the CRO have to be initiated by the CEO, and a great CRO will use the CEO, leverage their time, when it’s needed.

Did you miss the other CRO Startup Series posts? Click to read Part 1, Part 2, or Part 3.

-Matt Blumberg, August 9, 2022.