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

There are tons of customer success veterans out there. So you can find folks to join you. Even just a few years ago, there weren’t enough folks when enough experience to be your first “head of customer success.”  Now there are 100s and 1000s.

But the bad news is, many can’t really do the job a start-up needs at a leadership level. I’ve watched so many VP/Head/Directors of Success hires just not work out … so I thought it might be a good time to update our quick interview checklist from a few years back.

In particular, being an individual contributor customer success professional does not always breed leadership.

So here are 9 questions that will tease out what type of candidate they are, what they know, and what they really can do for you:

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 — if any.
5. Tell me about the top 3 customers you 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.
9. Can you show me your QBRs and other documentation you’ve built for customers? You can peer straight into their mind.  And ask them what percent of their customers show up to QBRs.  It’s often very few.

So many folks in CS these days are either (x) reactive or (y) not close enough to product. That doesn’t work for most start-ups.

Published on February 26, 2023