What questions to ask before joining a startup?

- What are the founders' backgrounds? (Do the founder backgrounds match the industry/verticals that are being targeted)

- Do either of the founders have previous start up experience and or successful exits?

- In plain language, explain the business model and the value prop.

- What (and how much) research have the founders done to validate their product idea?

- Is there a pipeline of committed customers / early adopters?

- Who is the competition / who are the competitors?

- Why are you better?

- Why will $unicorn_comp NOT come into this market?

- Equity is a large part of my compensation. Can I see the cap table?

Demand answers in plain language, no flowery fluffy management-consultantese. Given your early stage employee AND c-level, I would expect nothing less than 100% transparency.

In no particular order:

- Why do you think you need a CTO? Why me?

- What is the business plan?

- What's the plan when the current idea fails and we need to change?

- What's the current funding runway?

- Why are you trying to solve this problem?

- What customers do you already have lined-up to pilot the solution?

- What's your plan for further funding if we're not sustainable before the runway runs out?

- What constraints have current investors applied to the business?

- What percentage of the business has been sold to angel/VC investors? How much more can/will be sold as the need arises to fund the business until it's profitable?

- What's the business' exit strategy (be bought, go public, stay private...)?

- Who's already on the team - and why?

- What leeway will I, as CTO, have to make hire/fire decisions for my team(s)?

What happened to the last CTO?

How many hours per week are you expected to work? ("We are a family, so we are together during Christmas." is a bad sign.)

Get the promised equity in written. An oral agreement is not worth the paper it is written on. Assume that they are worth $0 anyway, and ensure that you are happy with the cash you get.

Ask to see analytics specific to the business. If there's any exaggeration ("We already have product market fit") the graphs will tell you very quickly if that's the case. There is often a lot of embellishment among early founders when trying to hire. And if a company has much less traction, it might be reasonable to ask for more equity so it really affects you.

Talk to all the engineers who have worked there recently, where possible. Figure out how bad the tech debt is. Chances are it's pretty damn bad.

Then figure out expectations for your role. Chances are it's pretty damn high.

Then check if you can meet it. And from there you can figure out compensation and culture and all.

I think the key here is only a trust: - do you really genuinely trust the founders? - do you really trust your own intuitions if there’s a market and profitable future for the company/product?

All the rest might be useful, but not more reliable than that. If it’s a risky new venture.

Just go in assuming you’ll get screwed. You can learn something for next time.