Dear SaaStr: What Is the Playbook for a Successful Customer Success Team?

A good playbook for customer success is all about driving retention, expansion, and customer happiness while making it scalable:

  1. Hire Truly Product-Savvy Customer Success Managers at First
    Focus on hiring people who are customer-focused product nerds to start.  They need to just love your product, and know how to deal with its issues and solve them.  Don’t overcomplicate job descriptions with too many criteria—stick to 2-3 must-haves that are hard to train for, like customer empathy and B2B experience.  As CS teams scale, they often fill us with “process” folks who aren’t product experts — at all.  You cannot afford to hire any of these folks in the early days.

  2. Nail Onboarding, and Make It a Key KPI for CS
    Onboarding is where you win or lose customers. Measure time-to-value and/or time-to-go-live.  And relentlessly bring it down.  Founders are often surprised how many customers buy … and never go live at all.  20% or more of B2B customers that buy never truly go live for many reasons.  Whatever your rate is, bringing that radically down is one of the top ways to drive NRR, renewals, referrals, and more up.

  3. Truly Proactive Account Management
    Don’t just wait for customers to churn—monitor account health daily. Use metrics like product usage, NPS, and engagement to identify risks early. Build workflows to address issues before they escalate. The goal is to act before customers even realize they’re unhappy.

  4. Focus on Net Retention
    Net retention is the ultimate metric for customer success. It combines renewals, churn, and upsells. Everything your team does should drive toward improving this number. High net retention (120%+ for bigger customers, 110%+ for smaller ones, 100%+ for tiny SMBs) is a sign of a healthy, scalable business.  GRR and logo retention are also critical, maybe even more so as you scale.  But in the earliest days, NRR is the simplest core metric for Customer Success.

  5. Leverage Product for Time-to-Value
    Your product is your best tool for customer success. Use it to guide customers through onboarding and deliver value quickly. The faster they see ROI, the more likely they are to stick around. This also reduces the burden on your CSMs.

  6. Incentivize the Right Behaviors
    Align your CSMs’ incentives with customer outcomes. Bonuses should be tied to metrics like net retention, upsells, and customer health scores—not just activity metrics like calls or emails. This ensures the team is focused on results, not just effort.  And be very careful if you have Customer Success report to a CRO or to sales.  That may (or may not) be the right call, but it almost always leads them into focusing more on upsell, and far less on true customer happiness.  Be careful here.

  7. Invest in Relationships.  Show Up Much More.
    Way too many CS execs think they are “relationship builders” — but don’t really do the building.  Go there.  Create clear quotas for meetings, both on Zoom and for bigger customers, IRL.  You have to go meet your bigger customers in person.  Even today.  This is especially critical for enterprise accounts, where relationships often determine renewals and expansions.

  8. Make Customer Success a Company-Wide Priority
    Customer success isn’t just the CSM team’s job—it’s everyone’s. From product to sales to marketing, every department should be aligned around making customers successful. Think of it as an hourglass: sales fills the top, but customer success drives the bottom half—renewals, upsells, and referrals.

  9. Measure Everything.  And Drive it Up Quarterly.
    Customer success needs to be data-driven. Track metrics like churn, NRR, time-to-value, and customer health scores. Use these insights to continuously improve your processes and prove the ROI of customer success to the rest of the company.

  10. Start Early.  At Least as Soon as You Have 2 Large Customers.
    Don’t wait until you’re at $5M or later to invest in customer success. Hire your first customer success manager as soon as you have even 2 Big Customers.  Their only job at first being to make those 2 wildly successful.  And hire a Head of Customer Success as soon as you have a repeatable sales motion. The earlier you start, the less time you’ll spend putting out fires later.  You can’t do it all yourself.

And a great related deep dive here:

How to Build a World-Class Customer Success Machine: Top Lessons from the CRO of Notion and VP of CS at GitHub

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