It’s so hard to find a CRO or VP of Sales. It can take months, even a year. You finally get someone onboard, and their first week … well … yikes. It’s not a great one. Any of these are a bad sign. A terrible sign, really:
- They don’t meet with any customers their first week
- They don’t have anyone strong to bring with them
- They don’t already know the product at least decently before they start
- They are focused just on “process”
These are terrible signs. Maybe this playbook works out at $200m+ ARR. Maybe. But not at your start-ups.
I’m sorry. but if your new Chief Revenue Officer doesn’t meet with any customers their first week, you made a bad hire. Full stop. The same goes for your Head of Product and Head of Customer Success.
They’ll never be hands-on enough, deep enough, to win. You’ll want to ignore these flags. Don’t. You’ll lose a year and so much momentum.
What They’ll Tell You (And Why It’s Wrong)
They’ll have excuses:
- “I’m still learning the business”
- “I need to understand our processes first”
- “I’m in discovery mode”
Don’t buy it. The executives who say this never make it at startups. Ever.
Why Customer Contact Week 1 Is Critical
In a startup, your revenue leaders need to be customer-obsessed from day one. Not process-obsessed. Not org-chart-obsessed. Customer-obsessed.
The best revenue leaders I’ve worked with? They’re talking to customers before they’ve even figured out where the bathroom is.
What to Do When You Realize Your Mistake
Own it. You screwed up the hire. Here’s how to handle it:
- Apologize to them. This is your fault, not theirs. You didn’t screen properly.
- Give them a package. Be generous. They left another job for you.
- Treat them with respect. No drama. No blame. Just a clean, professional exit.
- Move fast. Yes, even if it’s only been a week. Bad hires don’t get better with time.
The Pattern Never Changes
I’ve seen this play out 50+ times. The revenue leaders who don’t instinctively gravitate toward customers in their first days? They’re the same ones who will:
- Build elaborate processes instead of driving revenue
- Hire big teams before understanding the customer journey
- Focus on internal politics over external results
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More Time Does Not Help
It never, ever helps. Not once.
Customer contact in week 1 isn’t just nice-to-have. It’s the single best predictor of whether your revenue hire will succeed. That includes heads of customer success, and yes, heads of product too.
No exceptions. No matter their pedigree. No matter how “nice” they are.
If they’re not talking to customers immediately, they’re not who you need. Apologize, but fire fast. Hire better next time.
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