Dec 14, 2025
Why I created a 90-day Customer Success playbook after 11+ years across 4 startups and scale-ups and what CS leaders should focus on first.
If you’ve ever interviewed for a senior Customer Success role, there’s a good chance you’ve been asked the same question I have often at the final stage:
“Please prepare a 90-day onboarding plan of how you would drive NRR and ARR growth”
Over the years, I spent a lot of time putting these plans together. Thinking through priorities, risks, quick wins, and how to communicate confidence without over-promising. And after a while, I realised something important:
The exercise was never really about the plan.
It was about how you think as a Customer Success leader. In conversations with CS leaders, many of whom are now friends, I’ve seen the same patterns repeat as they step into new roles. There are familiar traps, a handful of meaningful quick wins, and lessons that only become obvious in hindsight. I wanted to capture those and share them.
The experience behind the playbook
Over the last 11+ years, I’ve worked across four startups and scale-ups as a Customer Success leader.
I moved roles deliberately to accelerate both experience and salary and I genuinely loved each one. But every move came with new lessons, new failures, and new insights.
Some 90-day plans landed brilliantly.
Others looked strong on paper but didn’t survive in reality.
The patterns were impossible to ignore:
The same expectations placed on CS leaders, regardless of context
The same pressure to “fix churn” quickly
The same assumption that CS can create clarity instantly often with incomplete data
And the same gap between what boards want to hear and what teams actually need
So I wrote them down to not only remind my ageing memory but to help others.
What new CS leaders can get wrong
Most 90-day plans fail for one of 3 reasons and I have done them all at some point.
Confusing activity with impact
Long task lists don’t equal progress especially in Customer Success. I always fell into this trap early on. I was so eager to please and make a real difference. Great Customer Success qualities include energy and empathy - point this is the right direction and it is very powerful but misfire and you will burn out and so will those around you.Underestimating inherited complexity & chaos
CS rarely starts with a clean slate. You inherit customers, processes, tooling, expectations, and history.Prioritising speed over credibility
Moving fast matters but not at the expense of trust with customers, teams, and leadership. Someone once said we need to 'slow down to move faster.' I love this phrase and its very true.
The strongest plans I’ve seen (and delivered) were grounded, commercially aware, and deliberately phased.
They balanced listening with action.
Insight with momentum.
Confidence with realism.
What the 90-Day Customer Success Playbook actually is
The 90-Day Customer Success Playbook is a practical guide for CS leaders stepping into a new role or founders building Customer Success for the first time.
It’s designed to help you:
Establish credibility quickly
Understand what really matters in the first 90 days
Avoid common traps that slow CS teams down
Create a plan that resonates with boards, investors, and operational teams.
Rather than theory, it’s built from real scenarios.
The playbook breaks the first 90 days into clear phases:
Discovery & listening - understanding the business. teams, customers, risk, and reality
Assessment - churn drivers, customer health, team structure, and gaps
Prioritisation - focusing on what will actually move retention and NRR
Momentum - creating confidence without overwhelming the team
It’s calm, structured, and deliberately practical. I don't want anyone to become a burnout CS leader!
Who this playbook is for
This guide is especially useful if you are:
A new or aspiring Head / VP of Customer Success
A CS leader preparing for interviews or board-level conversations
A founder who knows CS is critical but isn’t sure where to start
A team that feels reactive and wants structure
If you’ve ever thought “I know what I want to do but how do I articulate it clearly?”
This was written for you.
👉 [Explore the 90-Day Customer Success Playbook]
If you would like to learn more about how Elevate Customer Success can help you contact me for a no obligation conversation.