A Quick Diagnostic for SaaS CEOs, Founders, and CROs

1: LEADERSHIP SELF-AWARENESS

Has the CS leader proactively sought mentorship, coaching, or external support to evolve their leadership style?
Are they open to feedback from peers, execs, and frontline CSMs?
Do they show signs of adapting from player-coach to organizational leader?
Have they acknowledged gaps or challenges that come with scale?

2: STRATEGIC THINKING & EXECUTION

Can they articulate a clear strategy for Net Revenue Retention (NRR)?
Do they have a structured plan for segmentation (high-touch, low-touch, tech-touch)?
Are QBRs, onboarding, renewals, and escalations standardized and measurable?
Have they built strong cross-functional partnerships with Sales, Product, and Finance?

3: SCALABILITY & SYSTEMS

Is the CS function tracking renewal and expansion forecasts in a consistent way?
Are there defined processes and playbooks across different segments?
Can they manage and lead a team of 10–50+ CSMs through managers and leads?
Is there visibility into customer health, risk, and expansion opportunities at the exec level?

4: TEAM HEALTH & CULTURE

Are they attracting and retaining high-performing CSMs?
Is the team engaged and clear on goals and metrics?
Are 1:1s, enablement, and coaching embedded into their weekly rhythm?
Is CS culture aligned with the overall company values and growth strategy?

5: OUTCOMES & OWNERSHIP

Is CS hitting retention and expansion goals consistently?
Is the leader held accountable for NRR and CS-led revenue?
Do they own a seat at the exec table with meaningful contribution to GTM strategy?

Scoring Guide:

✅ 18–20 checks: Your CS leader is scaling well—invest in them further
✅ 14–17 checks: Solid foundation—may benefit from coaching or fractional support
✅ 10–13 checks: At risk—strongly consider upskilling or succession planning
✅ <10 checks: Misalignment likely—time to rethink leadership fit

This checklist offers a clear, executive-level framework to assess whether your Customer Success leader can truly scale with your company’s growth. Designed for CEOs, founders, and CROs navigating the shift from early-stage hustle to operational scale, it evaluates your CS leader across five critical dimensions: self-awareness, strategic execution, scalability, team leadership, and business outcomes. By systematically checking for the traits and systems required at the $20M–$100M+ ARR stage, you can determine whether your current leader is equipped to drive Net Revenue Retention—or if it’s time to invest in coaching, support, or a leadership change.