Dear SaaStr: What Should My New VP of Customer Success Be Doing In The First 30-60-90 Days?

Here’s how I’d structure their 30-60-90 day plan to ensure they’re focused on the right priorities:

First 30 Days: Meeting With Customers — ASAP.  And Deep Dive and Assessment

1.  Meet with Customers.  Starting Week 1.

This is non-negotiable. They need to meet with at least 20-30 customers in the first month, especially your largest accounts. The goal is to understand their pain points, what’s working, and what’s not. If they don’t prioritize this, it’s a red flag. Customer Success starts with listening.

2. Audit the Current CS Processes

Have them evaluate your onboarding, renewals, and upsell processes. Are there gaps? Are customers hitting value milestones quickly enough? They should identify bottlenecks and inefficiencies in the current workflows

3. Analyze Churn and Expansion Data — And Onboarding and Time To Value Data

They need to dig into your churn and NRR metrics. What’s driving churn? Is it product gaps, poor onboarding, or lack of engagement? Similarly, where are the upsell opportunities? This data will guide their strategy moving forward.

Equally important is onboarding and time-to-value.  Almost every B2B company is doing worse here than they could be.  You are just wasting hard won and hard closed customers if you don’t onboard close to 100% of them as fast as possible.

4. Build Relationships Internally.  And Helping Almost Immediately.

They should spend time with Sales, Product, and Marketing to align on goals. For example, are Sales setting the right expectations during the sales process? Is Product addressing the features customers are asking for? CS doesn’t operate in a silo.  If that’s what you are seeing the first 30 days, it’s a red flag.

Too many CS leaders fail this 4 part test.  They aren’t going to work out.  Sorry.

Next 30 Days (Days 31-60): Strategy and Quick Wins

1. Refine Onboarding

Onboarding is often where churn starts. They should simplify and optimize the onboarding process into 4-5 key steps that deliver immediate value. The faster customers see ROI, the stickier they’ll be.

2. Implement Customer Health Scoring

If you don’t already have a robust health scoring system, this is the time to build one. It should include both leading indicators (e.g., product usage, engagement) and lagging indicators (e.g., renewals, upsells). This will help the team proactively address at-risk accounts.  It’s not magic, but it is critical.

3. Pilot a High-Touch Program for Key Accounts

With a few $100K+ clients and potential $100k+ clients, you need a white-glove approach for your largest accounts. Assign dedicated CSMs to these accounts and create a structured engagement plan (e.g., quarterly business reviews, regular check-ins).  And go visit them in person.

4. Identify Upsell Opportunities

Start building a playbook for expansions. What additional value can you offer your existing customers? Whether it’s more seats, new features, or premium support, they should create a clear upsell strategy.

Final 30 Days (Days 61-90): Execution and Scaling

1. Roll Out a Scalable CS Framework.  With A Real AI Component.

By now, they should have a clear understanding of what’s working and what’s not. It’s time to implement scalable processes, like automated onboarding emails, in-app guides, and self-service resources. This will free up the team to focus on high-value activities.  And everyone will be expecting it to be AI-first today.

2. Drive NRR Improvements

There is always room to grow NRR. They should focus on driving expansions and reducing churn to push NRR to 120%+ for enterprise, 110%+ for mid-market, and 100%+ for SMBs. Even a small improvement here can have a massive impact on your valuation.  And revenue retention.

3. Measure and Report Progress

They need to start showing results. Are churn rates improving? Are customers hitting value milestones faster? Are upsells increasing? They should prepare a metrics-driven report to share with you and the leadership team.

4. Hire and Train the Team.  Including their AI Team.

If your CS team is understaffed or lacks the right skills, they need to address this now. Great CSMs can make or break your customer relationships. Invest in training and hiring to build a world-class team.

 

The key is to balance quick wins with long-term strategy. By the end of 90 days, you should see tangible improvements in customer engagement, retention, and expansion.