The CRO Paradox

No. 103 | The best chief revenue officers make you uncomfortable. That's the point.

“Always be closing.” — Blake, Glengarry Glen Ross (1992)

I sat down with Geoff Schiller yesterday in New York. He was our CRO when we sold POPSUGAR, and he’s now CRO of Vox, which is where POPSUGAR lives today. We worked together for over six years and have the kind of relationship that only comes from being honest with each other through hard moments. These days he shares the big career moments with me before almost anyone else, which tells you everything about what trust looks like when it’s actually been earned. At some point, halfway through my Diet Coke, I found myself thinking about what made Geoff so good at that job. The answer wasn’t complicated. He made me uncomfortable. Constantly, and on purpose.

What he taught me, over time, is that the best thing you can do with a great CRO is give them a long leash. They’re already carrying the number in a way nobody else in the building quite does. The more you insert yourself, the worse the outcome. Time spent and results are inversely proportional. The founders who figure this out stop managing and start protecting. They create the room. The CRO figures out the rest.

The CRO is the most miscast role in the consumer company org chart. Founders hire for likability because revenue conversations are already uncomfortable, and the impulse is to soften the friction with someone warm, someone easy, someone the team enjoys having around. The result, almost universally, is a CRO who’s great at internal relationships and mediocre at the actual job. The pipeline looks fine on slides. The board meeting feels productive. The numbers don’t move.

The CRO’s job is structurally adversarial. Not adversarial to the company, but adversarial to comfort. A great CRO operates from one assumption: the sales org is not the problem. The product, the marketing, the pricing, the category, that’s where the answers are. And so the leaders of those departments go fix them, partly because they have to, and partly because they want to prove the CRO wrong. That posture alone makes the whole company perform better.

It wasn’t just Geoff. Kristine Shine was POPSUGAR’s first CRO. She made me uncomfortable constantly. When we closed a $300,000 custom deal with Pepsi, I told her we weren’t in the business of building custom shoes for every brand that walked in. She pushed back. When the McDonald’s deal came through, Lisa was furious. Kristine held the line. She knew what the business needed commercially, even when it created friction with what we wanted creatively. She took us from zero to $40 million in direct revenue, building the commercial foundation that everything after it was built on. Without that foundation, POPSUGAR doesn’t become what it became. Without those conversations, there is no foundation. Neither of us always loved them. OOn her last day, I told her she was the one person in the office who made me look in the mirror. I meant it as a compliment. She knew that.

Most founders confuse this friction with a culture problem. They call it “not a fit.” They hire someone warmer, someone who nods more. The revenue conversation doesn’t go away. It just stops being honest.

The pattern is always visible early. When a prospective CRO spends most of the interview agreeing with your assessment of the market, you have your answer. They’re performing alignment. That phrase deserves its own sentence, because it’s exactly what’s happening: a skilled person reading the room and giving you what you want instead of what you need. A great CRO doesn’t perform alignment. They probe. They push back on the TAM. They ask about the customer segment you quietly stopped talking about. They’re trying to figure out if the business is real, because if they take the role, their name is on the number.

What separates the good ones is scar tissue. They’ve run a channel that broke and rebuilt it. They’ve managed a team through a missed quarter and owned it honestly. They know what a slipping forecast looks like before it becomes a narrative problem. That history lives in them differently than any logo on a resume, and it shows up in the first conversation if you’re paying attention.

There’s a version of this role that shows up constantly in consumer companies, the CRO as culture ambassador, morale builder, the person who fires up the sales team before a big quarter. That person is useful. They’re just not a CRO. They’re a VP of Sales with a bigger title, and over-titling that role creates a gap at exactly the level where the company needs someone to hold the line.

The question I ask now, when a founder describes their CRO hire, is simple. Do they push back on you? Not once, not in the interview, but as a pattern. If the founder pauses, I already know. If they search for an example and come up short, I already know. If the sales team loves them and the board loves them and everyone in the building thinks they’re great, I already know. They hired someone they like. They optimized for the feeling in the room instead of the truth in the numbers. Every founder does it at least once. The ones who build something lasting don’t do it twice.

If you don’t feel that discomfort in the room, you’ll feel it later in the numbers.