Maturing Your Customer Success Function

Featured Article

So, you’ve outgrown the startup phase? Congratulations. Now comes the hard part.

We’ve been discussing medium enterprises for the last month – but now it’s time to take it up a notch to talk enterprises. And specifically, how to scale your operations properly. 

Let’s get into what I’ve learned scaling customer success teams in the past – and how to build a practical strategy.  

Feeling messy? Sounds about right.

71% of CS leaders at $10-50M companies admit their systems are held together by duct tape and hope. Let’s just say if you feel like you’re constantly putting out fires – you’re definitely not alone.

The symptoms may sound familiar:

• Headcount isn’t keeping up with support tickets

• Customer experiences change depending who’s managing the account

• Data scattered across fragmented systems

• Nothing’s in place to predict or prevent customer churn

• You keep trying to emphasize CS to the board. But guess what? You don’t have the numbers on hand to back it up.

Thunder only happens when it’s raining? 

More like bottlenecks only multiply after downpours of growth. 

It’s time to level up. 

Replace those spreadsheets that worked back in the day but now are leaking revenue. 

Upgrade your “we’ll figure it out” and “all hands on deck” mentality with a proper strategy for landing (and keeping) enterprise clients. 

Four Strategic Shifts That Stick

In my experience, it all comes down to these areas:

1. Build a specialist team

Generalists plateau. Build up an expert team that reflects sophistication:

• Enterprise Account Teams (for strategic clients)

• Industry Experts (who speak your clients’ operational language)

• Technical Success Architects (for complex deployments)

• Customer Insights Analysts (turning data into action)

2. Invest in your tech

Disconnected tools create blind spots. And honestly, messy systems are just going to cost even more down the line. Switching to a super-efficient, integrated stack could literally transform your business. I’m talking…

→ 50% faster insight generation (no more spreadsheet archaeology)
→ 30% earlier churn detection (before the account goes dark)
→ 25% more expansion revenue (systematic opportunity identification)

3. Systematize the customer experience

Get super clear on your critical 20% – then make sure you have a prescriptive success plan to make sure your team is delivering seamlessly every single time. Create well-documented, structured core processes: 

• Client onboarding that delivers value from Day One

• Health assessments that actually predict risk (use AI-enhanced scoring tools to factor in sentiment, usage, and market conditions)

• QBR frameworks to drive accountability

• Clear escalation paths when issues crop up (you know they will! So have a plan.)

4. Measure and track more than you think

If you want to predict long-term success, you have to look past renewal rates and revenue. Start gathering insights around:

• Time-to-Value (how quickly clients achieve their first win)

• Value realization dashboards that update in real time 

• Adoption Depth (usage patterns of power users vs. laggards)

• Commercial Impact (revenue protected/created per intervention)

Where do you actually start?

I get it. You’re already underwater at work – how are you supposed to achieve all of this at the same time?

Here’s where I start in the first 100 days. It’ll get you moving the needle in the right direction without demanding too much.

1. Consolidate Your Data Foundation
Companies with unified client data achieve 2.3x higher revenue predictability. Start by mapping:

• Implementation timelines

• Support touchpoints

• Product usage patterns

• Commercial milestones

2. Automate the Invisible Tax
Recover 1,375+ hours/quarter by eliminating:

• Manual data entry

• Cross-system reporting

• Ad-hoc status updates

3. Prototype One Specialized Role
Prove the model with:

• A Technical Success Lead for your most complex deployment

• A Vertical Strategist for your largest industry segment

• A Renewal Architect to own expansion forecasting

Your maturity development over time will look something like this…

And the payoff?

Let’s just say it’s worth it. Teams who get all the way to that Lead stage consistently see:

• 85%+ gross retention in enterprise tiers

• 40% faster time-to-value for strategic accounts

• 3x higher cross-sell conversion rates

This isn’t about scaling for scale’s sake. It’s about building an operation designed around customer success. Growth has gotten you here – but scaling is what’s going to keep you from plateauing. So go make it happen.

P.S. Great customer education does more than inform. It transforms how customers work. This is how you turn users into advocates. I talk more about this on LinkedIn.

Tomas

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Deep Dive

What We've Been Reading

Amaze Every Customer Every Time: 52 Tools for Delivering the Most Amazing Customer Service on the Planet by Shep Hyken

What We've Been Listening Too

Customer success Is Not Sales by The Customer Success Channel