Stay #2 at a very early startup or become #1 of a department at a much larger startup?
Looking for career advice from people who have been in high growth startups.
I’m currently very early at a startup and effectively the #2 operator outside of the founders. I work extremely closely with them and have a lot of influence over how the company is being built.
Current comp:
• $120k base
• $24k target bonus
• 30% of gross commission on deals I personally source
• Company averages around 12.5% commission, so effectively ~3.75% of sourced premium goes to me
• 0.25% equity from joining very early
• Fair amount of autonomy
• Allowed to do occasional consulting/side deals as long as they don’t interfere with the job
The biggest upside is probably the exposure. I’m close enough to the founders that I’m involved in decisions well outside a normal department head role: operations, distribution, hiring, partnerships, product, strategy, etc.
Alternative opportunity would be joining a substantially larger/later stage startup as the #1 person running a department/team.
Potential compensation there:
• $200k to $250k base
• OTE bonus potentially another $200k to $250k for hitting roughly 2x base quota
• Equity unclear, but potentially earn additional equity through sales/performance
• Much larger team/company and significantly more resources
So potentially $400k to $500k OTE versus ~$144k fixed/target today plus commissions and early equity.
The part I’m struggling with is career trajectory.
At the smaller company, I’m basically learning how an entire startup gets built from a few feet away from the founders. If it succeeds, I could potentially grow into a COO/President type role or have a much stronger foundation for founding something myself.
At the larger company, I’d have a much bigger compensation package and get experience being the clear #1 leader of a meaningful function, managing more people, revenue, budgets, processes, etc.
So:
Would you rather be the #2 person close to the founders of the entire company, or the #1 person in your function at a much larger startup?
How much compensation would you realistically leave on the table for founder proximity, early equity, and broader operating experience?
And for people who made either choice, which one ended up being better for your career 5 to 10 years later?