“I’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].”

Post-launch, metrics:

• What key metrics are you tracking around the success of the business? How are you doing on each of them? — 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? — compare this to duration of time to assess pace of growth; compare this to valuation to assess if it’s richly valued
• What’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? — understand slope of trajectory
• How much of revenue growth is driven by new customers vs. existing customers paying more? — ideal: mix of both; existing customers paying more is a great sign
• What channels are your biggest growth drivers? — 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? — 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 you’re comparable to? — get external benchmarks for how big this can be
• What’s your runway based on current burn? How do you expect that to change in the next 3-6 months? — 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? — check how far along they are

Strategy / org, applies to everyone:

• How has the economic climate impacted your roadmap? What product areas are you doubling down vs. cutting back from? — check focus and ability to adapt
• How do you make decisions about what to build? Who calls the final shot? — check if this fits with how you prefer to work
• Who are your best customers? What have you learned about them? — check that they have a deep understanding of customer needs
• What are your customers’ biggest objections to adopting / paying for this solution? — 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? — check their ability to think and execute on the long-term
• Do you view [COMPANY] as product, sales, eng, design or marketing-driven? Why? — check if this fits with how you prefer to work
• Let’s assume everything goes to plan. What will [COMPANY] look like? — check long-term vision
• On the other hand, let’s assume things don’t go to plan. Why would [COMPANY] fail? — check rigor of thinking
• What's the moat that you’re building? — long-term value comes down to building something defensible
• What sort of progression would you like to see for someone in my role? — see if their expectations line up with what you want to do
• What would make someone a uniquely great fit for this role? — see how much of a shoe-in you are for this role
• What are the top challenges the business is facing today? — check if you’re excited about these and are uniquely suited to help them
• What are the top challenges you’re facing as a founder / leader? — 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? — churn is inevitable, important to know why people don't work out
• Based on the employee feedback, what have been the top pain points? — this is good to ask of multiple people to get different perspectives
• If you could change anything, what would you change about the team? — also good to ask of multiple people