5 Things I’ve Learned About Hiring Customer Success Leaders for $1M to $10M ARR Companies
Five questions to answer before hiring a first VP of Customer Success, plus five lessons on hiring CS leaders. Helps founders choose between a Head/Director and a VP.
The short version
Second edition 2026.
5 ideas you can use this week
Build the foundation first
Before hiring a VP of Customer Success, check you have clearly defined CS metrics, well-informed KPIs, a strong CS team and a clear CS strategy.
Set a baseline
Know your current retention, churn, satisfaction, acquisition rate and customer lifetime value, so you can measure the new leader against your organization's goals.
Owned the bus, not borrowed the keys
Look for a leader who has created and executed a playbook, not one who delivered someone else's plan. Directors or Heads of CS ready to step up can also be a strong option.
GTM fit beats domain expertise
Match experience to your go-to-market and CS motion: product-led or sales-led, tech touch or high-touch strategic accounts, consumption-based or licence revenue.
Be sure it is a VP you need
If the first CS hire involves a lot of hands-on work and direct client management, a Head or Director may fit better than a VP.
Questions
Get certified on the Framework
The CCSMP certification (Certified CSM Professional) is built on the Practical CSM Framework: five levels in three packages, for individuals and teams.