How I’d Approach My First 90 Days as VP of Customer Success
A new VP of Customer Success gets asked for a plan almost immediately. The temptation is to show up with one, built on whatever worked at the last company. I'd resist that. The first 90 days go a lot better when the plan comes out of what you hear in the first 30.
This is how I'd break it up, whatever the company. Three phases, each with a clear job.
Days 1 to 30: listen, learn and map
The goal of the first month is trust and understanding. I want to know the team, the customers and the internal partners before I change anything.
That means a 1:1 with every CSM, every CS leader, and my counterparts in Sales, Product, Support and RevOps. I'd ask each of them where the customer lifecycle breaks and where handoffs get dropped. I'd also get on customer calls, at least ten of them, across small and enterprise accounts, because the voice of the customer sounds different live than it does in a slide.
In parallel, I'd audit the machinery: team structure, processes, health scoring, segmentation logic, the stories people tell about why customers churned, and NRR trends. The churn stories are usually the most revealing part.
By day 30 I'd want three things on paper. An honest assessment of strengths, weaknesses, opportunities and threats, drawn from both the team and customers. A short brief on what I heard from stakeholders. And agreement with the executive team on what CS will prioritize for the next 60 days.
Days 31 to 60: design and align
Now I'd start designing. The main work is a future-state customer journey for each major segment, with small and enterprise customers mapped separately, since their paths rarely look alike. If you haven't done this before, I've laid out how I approach journey mapping.
From there, I'd redesign onboarding and success planning, and build a health score around leading indicators of growth instead of lagging activity. A health score almost always needs some rework in a new role, and one that actually predicts churn is worth the effort.
The other half of this phase is alignment. I'd work with Sales and Product to set up better feedback loops so what CSMs hear from customers reaches the people who can act on it. And I'd get the team aligned around the outcomes customers are trying to reach, not the number of touches we make.
The output here is a future-state journey by segment, an onboarding framework, and a brief on how we'll measure health, adoption and expansion going forward.
Days 61 to 90: pilot and prove
The last month is about testing the ideas on real customers before rolling them out everywhere. I'd run a new onboarding process with a small group of new accounts (five is plenty) and roll out success planning playbooks to the top 20 accounts. I'd launch a QBR format that connects usage to business outcomes the customer cares about. And I'd start an internal enablement program so the team has the skills the new processes assume.
Then I'd measure. A simple dashboard showing how the pilots are performing, a report on the expansion pipeline CS is generating, and an executive summary with OKRs for the next quarter. The pipeline report matters more than it looks. It's often the first time leadership sees CS as a revenue function and not just a retention cost.
Where you should be at day 90
If the three phases go well, the team knows what it's accountable for and is set up to drive both retention and expansion. Customers are getting to value faster. And Sales, Product and Finance have started to see CS as a partner in growth, because you've shown them something working instead of describing it.
None of this is fixed. What you learn in the first month should change the second and third. The one thing I wouldn't change is the order. Design before you've listened and you end up solving the wrong problems.
If you're stepping into a CS leadership role and want to pressure-test your plan, I'd be glad to help.
