Questions to ask when joining a startup

gistfile1.txt

product market fit 
      - do you have product market fit? How do you know?
          - press them on this, and see if they're honest about the parts that they don't know yet. 
          - what theses are they betting on (and what bets haven't played out yet?) 
          - what are you prioritizing, product roadmap wise, for next 6-24 months? why?
          - more importantly, what are you NOT prioritizing and why?
          - See: https://www.growthengblog.com/blog/the-best-metric-for-determining-quantitative-product-market-fit
          - https://www.growthengblog.com/blog/the-best-metric-for-determining-quantitative-product-market-fit
      - how well do they know the user / customer / pain point? 
          - their head of product / founder they should be able to answer all of your questions (just ask "why" 3-4 times and go down different rabbit holes) - it's a red flag if you as an outsider ask a question they haven't though about already 
      - do they do user research? how do they validate their product investments?
      - what's the NPS / any other data you can share on PMF?
      - what are the current biggest detractors / gaps in their product? 
          - what's their framework for thinking about whether to invest / double down in product strengths vs addressing gaps
      - what's your core metric for engagement / activity? Why?  (e.g., how are you defining "active user" )
          - flags: they choose an metric that isn't actually correlated with "people get value out of our product" -- e.g., for Pinterest, people saving a new pin is more important than number of users who logged in during a time period.
          - what's retention look like? does it flatten out at some point? ask to see a long-term cohort analysis retention curve.

Go To market 
      - what's the ideal customer profile?  how are they segmenting their customers? 
          - deal size, company size, industry / vertical
      - what's the sales motion?
          - inbound? outbound?
      - if applicable, do they know their CAC / LTV? 
          - for high transactional businesses / marketplaces, what's the CAC payback period? 

financials / metrics
      -  (note, these benchmarks for "good" are for SaaS companies):
      - unit economics: do you know your CAC and LTV? (more important for 
      - ARR and growth
          - existing ARR: every additional million is harder! 
          - looking for 40%+ in this current market (50-100%+ in previous environments). very early stage companies can definitely still have 100%+
      - net revenue retention (expansion and churn): 110% NRR is great
      - where are you on rule of 40 (most startups will fail this test, failing it isn't necessarily bad since this is a bar for public companies)
          - many companies now shifting away from measuring growth rate to measuring "sustainable growth" e.g. rule of 40 (growth rate plus profit margin -- profit margin is negative for startups). For series ~B SaaS "scale-ups", >0 on the rule of 40 is decent
      - what's your capital efficiency? (how much total have you burned over the life time of the company 
      - what's your burn?
      - what's your runway?

culture / values / people
      - All of the stuff in this post: https://charity.wtf/2022/01/29/how-can-you-tell-if-the-company-youre-interviewing-with-is-rotten-on-the-inside/
      - Consider the typical well-regarded well-run tech startup culture (e.g., highly collaborative / transparent / high ownership / hires smart people who are curious and growth-minded) - what separates your culture from them? 
      - assessing your Founder / manager / department head / senior leader you'd be working closely with:
          - ask people you interview with:
              - what's the thing you admire most about this person + examples
              - what's their weak spot / growth area?
              - have they ever done anything to lose your trust, or trust of others? what happened? 
      - assessing general caliber / strength of team you'll be on:
          - ask people you interview with: who's the person on the team you admire most, and why? ask for detailed examples of them showcasing that aspect