The Coin Flip VP of Sales

Have you ever heard something as ridiculous as this?

A company where the VP of Sales was chosen by a coin flip , and 40% of the “sales team” didn’t even know they were in sales.

I wish this was a metaphor. It wasn’t.

Three founders. Strong product. Smart people. Good funding. None of them wanted to own sales. So they flipped a coin. The “winner” became VP of Sales.

That was the foundation of the revenue engine.

Good. The post didn’t perform , but the story is strong. As an article, we go deeper. More analysis. More pattern recognition. Less punchline, more authority.

Here’s the expanded article version , still your voice, but structured and publishable.

The Coin Flip VP of Sales

Have you ever heard something as ridiculous as this?

A company where the VP of Sales was chosen by a coin flip , and 40% of the “sales team” didn’t even know they were in sales.

I wish this was a metaphor. It wasn’t.

Three founders. Strong product. Smart people. Good funding. None of them wanted to own sales. So they flipped a coin. The “winner” became VP of Sales.

That was the foundation of the revenue engine.

The Situation

I was brought in because the company was burning cash and couldn’t close deals.

The leadership told me:

• “We have a sales team.”

• “We have pipeline.”

• “The market is slow.”

• “We just need better execution.”

I ignored the CRM. I don’t trust dashboards. I don’t trust pipeline stages. I don’t trust what CEOs think is happening.

I talk to the people. And so I talked to the sales guys.

Out of five “salespeople”:

• Only one had any formal sales training.

• Two never wanted to sell in the first place and were just collecting a paycheck.

• Two thought they were developers who occasionally “help with demos.”

They didn’t even know they were considered part of the sales team.

This wasn’t chaos.

It was design.

This Isn’t Incompetence. It’s a Belief System.

What I saw wasn’t stupidity. It was ideology. And unfortunately, a very common one.

The belief that:

• Product matters more than sales.

• Great features create revenue.

• If the tech is good enough, customers will come.

• Sales is something intelligent people can “figure out.”

So developers become sales. Founders become VP Sales. Activity becomes “traction.” Meetings become “momentum.” CRM entries become “progress.”

And everyone feels better , until payroll approaches.

The Comfort Theater

Here’s the part most founders don’t like hearing:

Sometimes a sales structure isn’t built to generate revenue. It’s built to generate comfort.

Comfort for investors.

Comfort for the board.

Comfort for the founders themselves.

“Look, we have a team.” “Look, we hired a VP.” “Look, we’re doing outreach.”

But there is no architecture. No qualification discipline. No defined buyer strategy. No economic mapping. No decision-process control.

Just motion.

And motion feels productive , until cash runs out.

Why This Happens

Sales is the most emotionally uncomfortable function in a company.

It requires:

• Rejection.

• Clarity.

• Hard conversations.

• Accountability.

• External validation.

The product is controllable. Sales is exposure.

So founders gravitate toward what they control... And they assign sales to whoever draws the short straw.

In this case , literally.

The Cost

When sales are treated as secondary:

• Pipeline inflates artificially.

• Forecasts become optimism.

• Burn rate continues.

• Hiring decisions are based on hope.

• Investors are reassured with activity.

Then reality arrives.

Revenue misses. Runway shrinks. Confidence erodes. Emergency mode begins.

That’s usually when I get the call.

Sometimes it’s early enough to fix.

Often, the damage is structural.

The Real Problem

If your VP of Sales was chosen by convenience, politics, or avoidance , you don’t have a sales problem.

If your sales team doesn’t know they’re in sales, you don’t have a sales problem.

If activity replaces strategy, you don’t have a sales problem.

You have a leadership problem.

Revenue is not generated by titles. It’s not generated by features. And it’s definitely not generated by coin flips.

It’s generated by design.

And design requires ownership.

Reality always collects.

The only question is whether you face it early , or let it invoice you later.