Startup CXO

Chapter 69CEO‐to‐CEO Advice About the Sales Role

Matt Blumberg

What comes before a full‐fledged CRO? In most startups, the founder is the first salesperson. As startups scale, they add sales reps or maybe some form of a sales manager once there are more than a couple of reps. In the journey Anita writes about—from “selling on whiteboard” to “selling with PowerPoint” to “selling with PDF”—all of this is in the whiteboard stage and beginning to make the transition to PowerPoint.

Signs It's Time to Hire Your First CRO

You know it's time to hire a CRO when:

• You wake up in the middle of the night concerned about HOW you're going to make this quarter's number—not just WHETHER or not you'll make it (since you should know that as much as anyone), but that you aren't clear what the levers are, or what the pipeline/forecast details are, to get there.
• You are spending too much of your own time managing individual deals and pricing, or teaching individual reps how to get jobs done.
• Your Board asks you if you're ready to step on the gas and scale your revenue engine (e.g., move from PowerPoint to PDF), and you don't have a great answer and aren't sure how to get to one.

When a Fractional CRO Might Be Enough

A fractional CRO may be the way to go if

• Even at small volume where you wouldn't yet be ready for a full‐time CRO, your sales operation is very complex or to a very senior buyer, and a more junior sales team needs a fair amount of deal support from above.
• You're entering a new ...