The Top 8 Questions To Ask Candidates for Head of Customer Success

My Top 3, plus 5 more than will really tease out what type of candidate they are, what they know, and what they really do:

  1. What are the most important goals / KPIs for Customer Success at a company of our size and stage? You’ll learn if they focus most on account growth vs. retention vs NPS growth, and in what order.  And if they can “hold a number” in some fashion … or not.
  2. How often should we visit, and check in, with which customers?  If they don’t get out of the office, that can be OK for smaller deals (<$20k).  But it’s not a good fit for bigger deals and enterprise Customer Success.
  3. How do you think Customer Success should work with the Sales and Product teams? If they don’t have an answer, that may mean they don’t really know how to work at a SaaS start-up.  Later, CS becomes its own process island.   But in the early days, they should be at the vanguard of driving product changes, as well as being pulled into deals by sales that want help with more complex prospect needs.
  4. If we are on a tight budget, how should we staff the CS team? You’ll learn how they think about coverage ratios, and how much work they are willing to do themselves.
  5. Tell me about the top 2 customers you ever lost. What, if anything, could you have done to save them?  If they can’t answer this well, they aren’t a senior candidate.  Move on.
  6. How do you measure the potential size of an account? How do you know which ones can be grown, and which can’t? If they don’t know, account expansion isn’t their strength.  Maybe OK if you need support-on-steroids.  Not OK if you want to drive to industry-leading net negative churn.
  7. When you visit customers, what sort of agenda do you like to use?  If they don’t have a great answer, they haven’t really done enterprise customer success.
  8. How well do you tend to get to know the product’s ins-and-outs? Customer success after $10m-$20m ARR becomes a lot about process, and not too much about product limitations.  But it’s the exact opposite in the early days.  Don’t hire folks in customer success that don’t like to hack the product before $10m ARR or so.

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Published on June 2, 2019

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