Hiring for Customer Success isn’t just about finding great people. It’s about finding the right people for the right stage of growth.
The mistake I see all the time?
Startups hire a brilliant CSM but the person is a great maintainer, not a builder. Or they hire a senior CS leader but what they really need is a scrappy player-coach.
Over the years, I’ve worked with CS leaders and startup founders across different growth stages—from early hires to 10+ person teams. Here’s what I’ve learned:
Most hiring mistakes happen when you don’t know what kind of scale you’re hiring for.
Let’s walk through what to look for at every stage:
Stage 1: First CS Hire (0 → 1)
What you need: A generalist who can do a bit of everything: onboarding, adoption, success planning, support, even upsell.
What to look for:
- Strong ownership mindset
- Comfort with ambiguity
- Prior experience in cross-functional roles (e.g., support, implementation, solutions engineering)
- Ability to build from scratch and document what they’re doing
- Customer-centric and outcome-driven
Common mistake: Hiring someone too junior or too narrow. You need someone scrappy, not someone waiting for playbooks to be handed to them.
Stage 2: Early Scale (1 → 3 CSMs)
What you need: People who can handle accounts but also help you build the foundation. You’re still shaping motion, defining value, and stabilizing your delivery model.
What to look for:
- Pattern recognition across customers
- Comfortable handling volume and changing processes
- Team players who can contribute to building playbooks and internal best practices
- Adaptable with strong time management skills
Common mistake: Focusing too much on hiring for “customer empathy” instead of operational maturity. You’re no longer in one-off mode. You need repeatability.
Stage 3: Operational Foundation (3 → 6 CSMs)
What you need: Consistency. Process. Early specialization. This is where you start to create segments (high-touch, mid-touch, tech-touch) and need CSMs who can operate within a system.
What to look for:
- Strong execution discipline
- Experience working within a defined customer journey
- Ability to use data to inform decisions and risk detection
- Team members who can own pieces of enablement, tooling, or documentation
Common mistake: Not investing in enablement. At this stage, quality matters just as much as coverage.
Stage 4: Scaling Up (6+ CSMs)
What you need: Leads, managers, or specialists. You need structure. Think segment leads, strategic CSMs, or Ops support. Now’s also the time to introduce dedicated onboarding roles, renewals support, or pooled/digital CS models.
What to look for:
- Strategic thinkers and strong communicators
- Leadership potential: people who can coach, mentor, or lead pods
- Deep understanding of success metrics and commercial alignment
- Ability to balance customer outcomes with business goals
Common mistake: Scaling headcount without structure. Growth without defined swimlanes leads to confusion, burnout, and missed outcomes.
Bonus: When to Hire CS Ops
As soon as your team starts to hit 5–6+ CSMs and your leader is spending more time in spreadsheets and Salesforce than with customers or the team.
Don’t wait too long. Your strategy and performance will suffer if your leader is stuck doing systems work.
Scaling your CS team? Let’s get the structure right. 👉 Book a free 1:1 consultation to see if coaching or consulting can fast-track your next stage of growth.