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Hiring the Right Talent and Investing in Their Development
Build Teams That Own Relationships
Tomas
May 27th, 2025
Featured Article
We’re moving onto a new series all about building and scaling a customer function. In Part 1 of 5, let’s start from the foundation of your success – your people.
Why this matters:
CSMs with only SMB experience aren’t ready to manage stakeholder politics at an enterprise level. Maybe their technical skills are great, but when they’re thrown into the deep end to diagnose P&L leaks or maneuver procurement red tape…it’s like they’re fighting a tsunami in a kayak.
70% of enterprise churn can be traced back to misaligned CSM hires.
So let’s talk about how to fix this, shall we?
1. Hunt for the right profile
You’re looking for battlefield-tested talent – not ticket-closers. Enterprise CS calls for people who have been around the block (or should I say, around the corporate labyrinth) when it comes to managing complex relationships and driving revenue.
Look for these three key things in your next candidate:
Enterprise experience: They’ve managed multi-stakeholder accounts with 6-7 figure contracts.
Test it by asking: “Walk me through how you’d reduce churn with 5+ stakeholders vetoing renewal.”
Strategic chops: Can they advise CEOs, not just check boxes?
Think: Can this person frame answers in business outcomes and not just “managed accounts?”
Politically savvy: Bonus points if they’ve survived a leadership transition without losing a client.
Look for experience that showcases: Cross-functional influence, like aligning IT security concerns with HR rollout timelines.
Pro Tip: Screen resumes for outcomes, not tasks. Phrases like “Drove 30% expansion” > “Managed accounts.”
2. Interview Like a Pro
Forget “What’s your greatest weakness?”
Ask questions that expose how they handle enterprise chaos:
“How would you prevent churn if the CFO leaves mid-contract?”
“Walk me through a time you pushed back on an internal team to meet a client demand.”
What to listen for:
Examples of influence without authority (e.g., rallying IT to fast-track a deployment).
Business impact: Did their actions directly tie to retention or expansion?
3. Onboard to Win
A 30/60/90-day plan is non-negotiable.
Here’s the blueprint:
Days 1–30: Zero client contact. Instead, throw them into internal immersion (product deep-dives, process training).
Days 31–60: Supervised client calls. Let them shadow senior CSMs handling C-Suite escalations and have them take notes.
Days 61–90: Lead mock QBRs linking product metrics to EBITDA growth. Let them own 1–2 accounts with weekly coaching from a mentor.
Pro Tip: Simulate disasters. Throw them into a mock “security audit fail” scenario. How do they recover?
4. Develop, Don’t Stagnate
Ongoing training keeps your team sharp.
Invest in:
Monthly product drills: Updates, new features, and how to sell them.
Consultative skills: Teach them to ask, “What’s keeping your CFO up at night?”
Leadership pathways: High performers? Train them to mentor juniors or own strategic accounts.
I’ve seen teams wasting $250k/year per CSM on “training” that doesn’t actually bridge the enterprise gap. Focus on the development that drives results and improves communication and spotting customer churn.
5. Measure What Matters
Track KPIs tied to revenue, not activity.
Kill vanity metrics. “Number of calls made” means nothing if clients still leave.
Instead focus on:
Net Revenue Retention (aim for 110%+)
Expansion Revenue from existing workflows (upsells, cross-sells)
Days Saved in Time-to-Value (TTV)
Customer Health Scores (flag risks before churn)
Pro Tip: Tie bonuses and promotions directly to performance on these metrics. A SaaS team recently reported slashing churn by 27% after aligning comp plans with TTV acceleration.
6. Break Silos, Build Bridges
Enterprise success hinges on collaboration.
Build a culture that encourages departments and teams to actually talk to each other and work together:
Force cross-department handshakes: CSMs + Product Teams quarterly syncs.
Create a “Customer Solution Room”: Jointly tackle at-risk accounts with Sales, Support, and Engineering.
Feed intel to Product: Extract unspoken pain points and cross-communicate them. This can be the centre of your product roadmap!
Enterprise CS isn’t a department – it’s a revenue engine.
Hire for grit and strategic IQ, onboard like their first day decides a client’s fate, and measure what moves the needle.
Your competition is hiring “good enough.” But you? You’re building a team that clients can’t live without.
Next week, we’re going all in on how to build a culture that drives CS across your org. Hire right, train effectively, then make an environment that can’t fail.
Tomas
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