Should I leave IB for this offer?

Hi all,

Long time lurker, first time poster. Hoping to get a sanity check before I accept an offer to leave banking.


  • 1st year analyst at top BB in coverage group
  • Semi-target
  • Hate banking, and long term would like to be in VC / startup founder


  • Title: Chief of Staff (direct report to CEO)
  • Company: Series A tech startup that recently raised Series A from top VC fund
  • Employees: ~30 (growing to 100 with latest round of funding)
  • Location: Remote (Option to be in office)
  • Salary: $120,000
  • Bonus: "Merit Based"
  • Equity: Options vested over 4 years (current value of ~$75k)
  • Benefits: Unlimited vacation (mandatory minimum amount used), 6% 401k match, full health, dental, vision, and other small perks

Pros / Cons

  • Pro: Get to leave banking and work in an area I'm actually interested in
  • Pro: Solid salary (Not planning on living in NY or other high cost of living cities)
  • Pro: Equity upside
  • Pro: Hopefully better WLB
  • Con: Lower total compensation
  • Con: Giving up better exits later?
  • Con: Bad optics of leaving after a year?
  • Con: Uncertainty of startup success
  • Con: Limited visibility into bonus / career progression
  • Con: Less certain path. What is next?

What else should I be considering? Am I crazy to take this offer? Don't want to be blinded by how bad the past year in banking has been.

Thanks in advance everyone!

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Comments (7)

Jul 24, 2021 - 7:12pm

I wouldn't take it. No idea what the startup's prospects are but even with top VC backing there's a better than even chance it doesn't reach escape velocity. IB is better risk adjusted bet. Even if you were to just do your 2 years in IB and then seek out a similar role, you'd have such ridiculously improved optionality. And if at that point you still wanted to do a small startup thing and be chief of staff, first corp dev hire, whatever, you'd be able to negotiate for dramatically better comp, equity, etc. than now. The only possible downside career wise is if the startup you're talking about is the next Shopify and you missed out on being employee #31. Unlikely though

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  • Analyst 1 in IB - Gen
Jul 24, 2021 - 7:21pm

I would take it. If you hate IB and have long term goals to be in VC/startups then this is perfect. Not all VCs value banking experience and having a mix of banking skills and operational skills (Chief of Staff) would be great for setting you up in either being in VC or in the startup world should you ultimately decide to leave.

Also Chief of Staff is pretty ambiguous, but generally is almost like a COO-ish role, but sometimes has heavy admin duties. Given the comp level, it probably is more the former than the latter. To frankly exit after a year at $120K salary, $75K of stock/options (over 4 years, so ~$19K) with some bonus (say $12K or 10%), thats a $151K package which is very solid for a corporate exit, especially after a year.

One thing to note though is that the pressure under that role will probably be immense and even if you work less hours a week, the stress will probably be a similar amount. And that's "if" you work less hours a week, I've seen several instances where Chief of Staff people at startups work long hours.

  • Analyst 1 in IB - Gen
Jul 24, 2021 - 9:19pm

Not OP but curious how this works. I get the options vest over 4 years but are the 75k in options like a sign on bonus over 4 years or do you receive an additional 75k in options every year?

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Jul 26, 2021 - 1:07pm

Actually found this opportunity through the VC firm I interned with in college. I stayed in touch with the partner and he made an introduction. From my discussions with him, a lot of seed through series A companies are starting to hire chief of staffs along with a new round of funding

  • Investment Analyst in AM - FI
Jul 26, 2021 - 12:38pm

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