What Sets Great CSMs Apart? CS Leaders Share Their Observations

The best CSMs build deep, proactive relationships (Allison), lead with empathy to solve real customer problems (Abhishek), and stay laser-focused on tying customer goals to measurable outcomes (Andy).

A while back, I spoke with a few aspiring CSMs who asked a great question:
“What makes a great CSM?”

I shared a few lessons from my own journey, but it got me thinking: why not ask CS leaders who’ve seen the best in action?

So this week on Cracking the CS Code, I reached out to three CS leaders: Allison Skidmore, Abhishek Mangaraj, and Andy Chandler, and asked them about the one thing the best CSM they’ve worked with consistently did that drove results for both customers and the business.

Their insights? Practical. Powerful. Worth sharing.

This is what I learnt:

• Great CSMs build deep, multi-threaded relationships, act proactively before problems arise, and use data as their compass to drive consistent, high-impact customer outcomes.

• Great CSMs lead with empathy, dig into the “why” behind customer challenges, and go beyond the playbook to deliver solutions that drive retention, expansion, and long-term advocacy.

Allison

For Allison, the best CSMs she’s worked with are part connector, part mind‑reader, and part data detective. What sets them apart? They build relationships that go beyond the inbox, they act before anyone asks them to, and they let data light the way:

“First, they build multi‑threaded relationships on both sides of the partnership. Not just ‘Who’s my main POC?’—they go deep and wide. They align executive sponsors on our side with executive stakeholders on the customer’s side. They map themselves to business and IT leads, then strategically plug in support, services, partners, and sales to create a true ecosystem of connection.
The magic doesn’t just happen in QBRs or check‑ins; it happens over dinners, events, even early‑morning coffee walks—because people do business with people they trust, not logos they tolerate.

One of my favorite sayings? ‘The best time to build a relationship is before you need it.’ Great CSMs live this. They know that when things get bumpy—and they always do—it’s the strength of those relationships that keeps the wheels on.”

Next, they’re ridiculously proactive. They don’t just follow up; they follow through and even follow ahead. When they say they’ll do something, it gets done, better than expected. They prepare execs for meetings with precision and spot risk two steps out, not two weeks too late:

“I remember a customer whose adoption suddenly dropped after a round of staff turnover. We couldn’t reach the exec stakeholders. The CSM didn’t keep firing off emails—they discovered the CPO and CTO were attending the company’s annual charity golf event. We got a spot. Two days of face‑time with the CPO, CTO, and even the CEO reignited the relationship and rekindled the value.”

Most importantly, none of this works without data:

“The best CSMs treat usage telemetry like radar. They know which metrics matter, and when those numbers dip below a threshold, they don’t wait—they act. They prioritize accounts based on leading indicators, not gut feel. They follow playbooks, pull in resources, and tailor the response. They’re deeply connected across the company and know exactly where to find help to get the customer back on track.”

Want to start doing this today? Allison’s playbook:

1. Get crystal clear on your adoption metrics. What truly signals success or churn?

2. Map your stakeholders. Use LinkedIn Sales Navigator and fill the gaps.

3. Personalise outreach with tools like ChatGPT. Understand what your customers really care about.

4. Show up. Yes, in meetings, but also unexpected places. The best conversations often happen off the clock.

Bottom line: Relationships beat transactions. Proactivity beats reactivity. Data beats guessing. The best CSMs don’t just support customers; they orchestrate success across people, platforms, and possibilities.

Abhishek

For Abhishek, the best customer success managers do one thing consistently;
they approach every interaction with a problem-solving mindset rooted in deep customer empathy.

These CSMs don’t just walk through features; they dig into what the customer is really trying to achieve. They understand the business goals behind the ask and proactively align solutions, even if that means going beyond the standard playbook.

He shared an example of how one CSM on his team turned around a high-risk account:

“We had a customer at serious risk of churn due to perceived platform complexity and operational gaps.

Instead of reacting defensively, the CSM invested time to deeply understand their pain points. They re-mapped workflows, collaborated with product and tech to build interim solutions, and ensured high-touch support across teams.

The result? A complete turnaround. The customer didn’t just stay—they scaled 3x within a few quarters, expanded to multiple geographies, and became a referenceable promoter. That account alone drove over 200% NRR.”

For Abhishek, what validated this approach was a mix of powerful signals:

• Steady improvement in customer feedback.

• A noticeable drop in support tickets.

• Increased product adoption.

• And most importantly, renewal and expansion with zero pricing pushback.

Andy

Andy starts with a familiar pattern: most CSMs ask about a customer’s success metrics and dutifully log them into the CRM, but then stop there. Great CSMs go further:

“A great CSM asks where those metrics stand today, what targets need to be hit, and — most importantly — what the cost of missing them would be.
The key is to measure the impact your software is actually having on their business, not just their engagement with your product. Customers don’t generate value by logging in — they do it by achieving meaningful outcomes.”

Once a CSM understands the customer’s goals, Andy says the next question should be:
“What’s the business impact of hitting this target? What happens if you miss it?”
If the answer doesn’t include a number, great CSMs keep digging until they can clearly connect their work to the customer’s bottom line.

One example that stands out for Andy:

“We had an account that looked healthy on paper. Product usage was strong, but the customer had a completely different view of the value we were delivering. By digging into their true business objectives, we uncovered a misalignment, repositioned our value, and not only prevented them from going out to market, we actually grew the account by demonstrating a direct impact on their revenue.”

Bottom line: Great CSMs don’t just track goals. They translate them into business outcomes and stay laser-focused on the impact that matters.

Final Thoughts

Great CSMs don’t just manage accounts. They connect with people, solve meaningful problems, and drive impact that matters. Whether it’s building trust before it’s needed (Allison), leaning into empathy and action (Abhishek), or anchoring every effort to real business outcomes (Andy), the common thread is clear: they own the customer’s success like it’s their own.