Evaluating Your New CRO/CMO Before the Revenue Hits

Ladies, gentlemen.. welcome back.

I recently sat down with 6 Operating Partners to find out:

Why do revenue leadership hires fail? Why does it take so long to see the failure coming? What should a CEO or board actually be checking in the meantime?

Some of what came back surprised me and I don’t say that lightly after a decade of placing revenue hires.

A new revenue leader’s decisions take two to three quarters to show up as closed revenue. That’s roughly how long a sales cycle, plus ramp time, plus pipeline build takes in most B2B motions.

Which means “is revenue up?” isn’t the right question early in that hire’s tenure.

And the stakes are high.

Average CRO tenure right now sits around 23 months, against a median software buyout hold period of 5.4 years. The seat turns over roughly three times before exit. If you get even one of those wrong, you’ve lost a meaningful chunk of the hold period to a leader who was never going to work out. a four-time CMO turned operating partner, put a number on the downside. He estimates a wrong CMO hire at growth stage could cost roughly $5 million once you count two lost years, search fees, the churn of top performers, and the marketing spend that went in the wrong direction.

I built a detailed research report from these six conversations. Link to the report at the bottom.

So what should you be watching in the two quarters before the revenue number means anything?

That’s what this newsletter is about.

Let’s get into it.

Why “wait for the number” doesn’t work

At 90 days, the number in front of you is an inherited pipeline.. deals that were already moving before they walked in, closing on a timeline set months earlier by someone else’s work.

Alex Nechifor (one of the six operating partners I interviewed) put it well:

“I’ve seen people come in sitting on a good pipeline, close some deals, and have it all attributed to them. The past gets forgotten, and now they’re the superstar, having done almost nothing. It’s like changing presidents every four years. Most projects take time to come to life, and the sitting president takes credit for work that started two terms ago.”

Then there’s the other version.

Someone loosens the qualification bar a little on what counts as a real opportunity, and coverage ratios look healthy for a quarter or two, then the deals that were never qualified start falling out.

Either way, revenue at 90 days can’t tell you what you actually need to know.

The earliest legitimate signals are qualitative

The earliest legitimate signals that predict whether a revenue leader will work out are qualitative in nature.. the numbers may lie to you at this stage. The qualitative stuff rings true.

It shows up in whether the leadership team has agreed on the diagnosis, whether peers describe the same strategy separately, how the team behaves in a room without them prompting it, whether the CEO is getting headspace back, and how they react the first time they hit a real problem.

90-Day Read checklist

This takes actual legwork but none of it takes more than a few hours spread across a week, and none of it needs a single closed deal.

1. Strategic Planning. Have they actually sat down and figured out where this business wins and why? Who we win with, where the motion breaks, what we need to stop doing.
2. Peer Trust. Go talk to their C-suite and VP peers, separately. Ask the CRO and the CMO the exact same questions. Who are we selling to, and why do we win? If you get two different answers, or someone hedges, you’ve got two strategies running side by side.
3. Team Buy-In. Talk to their direct reports. Then just sit in on one of their team meetings as a fly on the wall. Is there actual structure? Do people leave with something they didn’t walk in with, or is it just a status round-robin? Barely anyone does this, and it might be the best signal you’ve got.
4. CEO’s Read. Be honest with yourself here. Is the CEO getting his or her time back? Can you say “thank God they’re here” and mean it, or is it more of a “we’ll see”? That hedge shows up way before anything else does. It usually means you still can’t tell what good looks like in that seat.
5. Progress on Big Initiatives. Is anything moving on the goals you set for this role? Look for leading indicators.
6. Red Flags. Did they install a prior playbook before understanding the context? Make structural changes before finishing an assessment? Catalog problems without proposing fixes? Top performers disengaging? Peers asking to exclude them from deals? Trust with the CEO visibly eroding?

Run these six, and I promise you’ll have the clarity long before the pipeline does.

Why CEOs sit on it anyway

Most of the time the delay is emotional.

This is a hire the CEO spent months building a case for. They ran the search, sold the candidate on the vision, sold the board on the candidate, and staked real personal credibility on the outcome. Reporting a miss shortly after making that case feels like reporting on yourself.

: CEOs think: I lose credibility with the board if I make another change, even though I don’t love the person I’ve got. Changing a sales leader is enormously disruptive. It’s a J-curve, you see the dip before you see the benefit.

And one finding that surprised me most:

A Partner at a European venture firm I interviewed for the research pulled up post-investment research and found that companies performing best through to IPO had higher executive turnover than the underperformers.

The companies that struggled were the ones that kept a bad-fit leader in the seat longer, hoping the numbers would eventually agree with a decision.

Waiting just kicks the conversation down the road, at a worse price, so have it now.

Set the date now

Put day 90 on the calendar the day you make the hire. Set the date while everyone’s still calm and nobody’s emotionally invested in a particular outcome yet.

When the date arrives, do the legwork.

If the read comes back mixed instead of clearly good or clearly bad, don’t leave it hanging. Pick three things this person needs to be doing differently, agree on them together, and revisit in another three months. If nothing’s changed by then, you make the call. It’s a lot easier than sitting with a vague, gnawing feeling for another two quarters.

We put together a detailed research report from these conversations. It has the complete one-page checklist, the specific red flags that tell you a hire isn’t going to work, and what to set up before the hire is even made so the 90-day read is fair to run in the first place.

Thank you for reading.. if you’d like to discuss this deeper, feel free to DM me.

Peace and love!

Graham