The First 90 Days: An Onboarding Playbook for New Customer Success Leaders

Starting a new Customer Success leadership role can be daunting.

You’re expected to make an impact quickly -often before you fully understand the business, the customers, the team, or the data. The pressure to “fix things” can be intense, and moving too fast or in the wrong direction can do real damage.

This playbook is a steady, experience-led guide to navigating your first 90 days with clarity, confidence, and intent.

Written by a VP of Customer Success with 25+ years in tech and over a decade leading Customer Success teams (at board level), it shows you how to diagnose reality, set direction, and build momentum without burning trust, credibility, or yourself.

What you’ll get

A practical, structured approach to your first 90 days, broken into 3 clear phases:

Days 0–30: Situation analysis & performance audit

• Understand the business, customers, team, and data
• Separate signal from noise
• Identify risks, gaps, and opportunities before making changes

Days 30–60: Build the CS vision & deliver early wins

• Define a clear Customer Success mission and operating principles
• Align engagement models to customer value
• Deliver visible improvements that build confidence and trust

Days 60–90: Establish credibility & demonstrate momentum

• Align leadership around a credible CS strategy
• Demonstrate early indicators of retention and growth
• Position Customer Success as a trusted driver of value

The playbook includes practical templates, prompts, and outputs for each phase not just advice, but tools you can actually use.

Who this playbook is for

• Heads of Customer Success / VPs of CS starting a new role
• First-time CS leaders stepping up from CSM or Manager roles
• Founders temporarily owning Customer Success
• CS leaders inheriting teams, customers, or processes that need stabilising

If you are starting or interviewing for your first Customer Success Leadership role and need structure and support then this playbook is for you. By following this playbook, you’ll move from uncertainty to clarity, avoid early missteps, and build credibility with your team and leadership.

About the author

Victoria Hamblin is Customer Success Leader based in Manchester, working with SaaS companies globally. She has spent the last decade building and leading Customer Success teams through growth, complexity, and change helping organisations reduce churn, improve retention, and build CS functions that scale.