Questions for private startups (post-launch metrics, strategy, org)

Again, there are a LOT of questions in this section. You probably won't have time to get to everything, so I would pick and choose based on what you're most concerned about. 

Reminder of set-up:
โ€œIโ€™d love to ask (the founders) some questions about the business to better understand how to evaluate my offer, and how I can be valuable to [STARTUP].โ€

Post-launch, metrics:

These are more sensitive questions, so itโ€™s best asked of founders / leadership team.
  • What key metrics are you tracking around the success of the business? How are you doing on each of them? โ€” this is a soft-ball if you're less comfortable with getting into the numbers; but still recommend digging into metrics below if founder does not proactively bring them up
  • How much revenue are you generating? How much of that is recurring? โ€” compare this to duration of time to assess pace of growth; compare this to valuation to assess if itโ€™s richly valued
  • Whatโ€™s your growth rate in terms of # (paying) customers? In terms of revenue? How have your growth rates changed in the past 3-6 months? โ€” understand slope of trajectory
  • How much of revenue growth is driven by new customers vs. existing customers paying more? โ€” ideal: mix of both; existing customers paying more is a great sign
  • What channels are your biggest growth drivers? โ€” ideal: organic like word-of-mouth, referrals, SEO; paid channels are ok but need line of sight into how they maintain their edge
  • What does customer retention rate look like? What does dollar retention rate look like? โ€” customer retention rate measures % of customers that stick around; dollar retention rate measures % spend that sticks around; possible to have >100% dollar retention rate through growing spend among active customers
  • Are there specific public companies that you believe youโ€™re comparable to? โ€” get external benchmarks for how big this can be
  • Whatโ€™s your runway based on current burn? How do you expect that to change in the next 3-6 months? โ€” 2+ years are ideal; burn should be maintained or reduced in bad markets
  • What sort of growth do you need to meet / exceed investor expectations for the next round? โ€” check how far along they are

Strategy / org, applies to everyone:

These questions can be asked of the founders or hiring manager โ€” also interesting to ask these of multiple people to see where team is aligned vs. not.
  • How has the economic climate impacted your roadmap? What product areas are you doubling down vs. cutting back from? โ€” check focus and ability to adapt
  • How do you make decisions about what to build? Who calls the final shot? โ€” check if this fits with how you prefer to work
  • Who are your best customers? What have you learned about them? โ€” check that they have a deep understanding of customer needs
  • What are your customersโ€™ biggest objections to adopting / paying for this solution? โ€” any strong product thinker has this top-of-mind
  • What's the plan to 2X, 5X, 10X, 100X from a product / sales & go-to-market perspective? โ€” check their ability to think and execute on the long-term
  • Do you view [COMPANY] as product, sales, eng, design or marketing-driven? Why? โ€” check if this fits with how you prefer to work
  • Letโ€™s assume everything goes to plan. What will [COMPANY] look like? โ€” check long-term vision
  • On the other hand, letโ€™s assume things donโ€™t go to plan. Why would [COMPANY] fail? โ€” check rigor of thinking
  • What's the moat that youโ€™re building? โ€” long-term value comes down to building something defensible
  • What sort of progression would you like to see for someone in my role? โ€” see if their expectations line up with what you want to do
  • What would make someone a uniquely great fit for this role? โ€” see how much of a shoe-in you are for this role
  • What are the top challenges the business is facing today? โ€” check if youโ€™re excited about these and are uniquely suited to help them
  • What are the top challenges youโ€™re facing as a founder / leader? โ€” get a sense for what you can help them with

If company >50 people:

  • Have there been people who have not worked out at [COMPANY] before? Why did they not work out? โ€” churn is inevitable, important to know why people don't work out
  • Based on the employee feedback, what have been the top pain points? โ€” this is good to ask of multiple people to get different perspectives
  • If you could change anything, what would you change about the team? โ€” also good to ask of multiple people

We're not done yet! See examples of good vs. excellent metrics in the next section ->