Most CS leaders I coach don’t struggle because they lack talent, commitment, or vision.
They struggle because they’re stuck in chaos mode.
🧯 Fielding escalations
🧠 Remembering every renewal in their head
📊 Manually piecing together forecasts
🔁 Constantly reacting instead of building
They’re not leading a team.
They’re managing a million moving pieces.
Sound familiar?
If you’re a VP or Head of CS at a growing startup, you’ve likely lived this. You start out doing everything to keep customers afloat. But as you scale, what used to work starts breaking.
You can’t operate on gut feel.
You can’t be the catch-all for every customer issue.
You can’t carry the business in your head anymore.
The reality is, many CS leaders get hired to be strategic, but get stuck being operational.
So let’s break down how to change that.
The 3 Signs You’re Stuck in Chaos Mode
Before you can fix it, you need to recognize it. Here’s what chaos-mode leadership often looks like:
1. You’re Always in Reactive Mode
Instead of driving proactive value, you’re caught in the churn of escalations, QBR prep, and last-minute saves.
2. You’re the Bottleneck
Every customer strategy, stakeholder conversation, or process question runs through you. Nothing moves without your brain involved.
3. You’re Building for Now, Not for Scale
The team is growing, but your systems haven’t. You’re duct-taping together fixes instead of building a model that scales.
What Strategic Leaders Do Differently
The shift isn’t about working harder. It’s about working differently.
Here’s what it looks like when CS leaders rise above chaos:
✅ They Create Systems
Instead of chasing renewals, they build playbooks, operating rhythms, and handoff processes that make outcomes predictable.
✅ They Build Thinking Time Into Their Week
They carve out time to review dashboards, spot patterns, and make intentional decisions, not just react.
✅ They Coach the Team to Own Outcomes
They’re not solving every problem. They’re building a team that can think critically, escalate smartly, and operate with confidence.
✅ They Lead Cross-Functionally
They’re not just sitting at the CS table. They’re influencing product, sales, and exec strategy through data, insights, and real customer impact.
This is what separates high-growth CS leaders from those who burn out in the weeds.
The Shift I Coach My Clients Through
If you’re serious about stepping into strategic leadership, here’s the mindset shift I help my coaching clients make:
From “How do I fix this?” to “What system needs to exist so I never have to fix this again?”
You stop solving the same problems over and over.
You start designing systems that solve them for you.
That’s how you scale. That’s how you lead.
Coaching Prompt
What’s one fire you put out this week?
Now ask:
→ What broke down?
→ What system (or lack of one) allowed it to happen?
→ What would it look like to fix the root cause?
That’s the shift. From firefighting to designing.
Want Support Making the Shift?
If you’re tired of reactive leadership and want to build a high-functioning CS org that runs with you, not because of you, I can help.
Inside coaching, we’ll build:
✅ A CS operating system that scales with growth
✅ Clear roles, rhythms, and reporting lines that reduce chaos
✅ Leadership habits and frameworks to help you focus on what actually moves the business forward
📅 Want to explore whether coaching is the right fit for you? Book a consultation call with me here. Let’s talk through what you’re navigating and explore whether coaching or consulting is the right next step to support your goals.