Titles are traps early on

Titles are traps early on!

“We hired our first salesperson and labelled him “VP” because ego was cheaper than cash.”

A common and costly mistake.

Premature titles often box founders into a tough choice: fire the loyal or freeze the company.

Smile Digital Health made this exact mistake.

CEO and Co-Founder Duncan Weatherston gave out a VP title when they were a team of 10.

Six quarters later the team hit 120 and that same badge turned into handcuffs.

The demotion cost more momentum than the promotion ever bought.

Titles are forecasts. Hand someone leadership stripes at ten people and you’re betting they can captain at a hundred.

The odds are brutal, the downgrade conversation happens too late, and what would have been a great IC leaves too soon because their ego is too hurt to stay.

Instead:

1. Start with IC labels only.

2. Let scope trigger upgrades (people, revenue, or complexity multiplie ten‑fold)

3. Move fast when growth outruns skill, re-seat or part ways fast.

Equity already promises upside. Save the brass until the org chart demands it.

Momentum loves accurate labels. Protect it.

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Enjoyed reading this?

Then check out my conversation on the focal podcast with Duncan Weatherston, Co-Founder and CEO of Smile Digital Health - a business that bootstrapped to $10M ARR and has >$50M ARR with $50M raised today.

Youtube | Apple Podcast | Spotify

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