Renewals are coming in and nobody has spoken to half of those properties since they went live. A couple of churned accounts surprised the founder. Support is busy, sales is busy, and someone suggests it is time to hire customer success. Sometimes they are right. Often the real gap is onboarding, or support, or a renewal process nobody owns, and a customer success manager hired into that gap ends up doing a different job than the one they were hired for.

This decision tree is for the first hire. Work through the questions in order and stop at the first one that gives you an answer. If you reach the end, hire.

Before you start: four facts

• How many live properties you have, and how many renew in the next two quarters

• Gross revenue retention for the last twelve months, and what share of the churn was a surprise

• How long a new property takes to reach first value, and what share never does

• Who currently speaks to customers after go-live, and how many hours a week they spend on it

If nobody can say what share of churn was a surprise, write that down. It is often the strongest single argument for the hire.

The decision tree

Question 1: Is the problem before go-live or after it?

Look at the properties that churned or went quiet. Did they ever reach first value?

• If most never got properly started: the gap is onboarding, not customer success. Stop here. Fix the onboarding process first, along the lines of how to reduce time to first value in hotel software, and revisit the hire in a quarter.

• If most reached first value and drifted later: go to question 2.

Question 2: Is support absorbing the customer success work?

Check what the support team spends time on beyond tickets: check-in calls, training new staff, renewal conversations.

• If support is already doing proactive work and the ticket queue is suffering: you probably need the hire, but be clear the role is proactive. Go to question 3.

• If support is overwhelmed by tickets alone: stop here. The first hire is a support hire. A customer success manager in this position will spend every day in the queue.

Question 3: Can the current owner of the relationship keep up?

Usually the founder or the salesperson who closed the deal is still the main contact after go-live.

• If they still speak to every account at least once a quarter and renewals arrive prepared: stop here. You do not need the hire yet. Write down the process they follow so it can be handed over later.

• If accounts are going a quarter or more without contact, or renewals are a surprise: go to question 4.

Question 4: Is the churn concentrated in one segment?

Split churn by independent hotels, groups and management companies, and by size.

• If one segment churns far more than the others, and that segment is a poor fit: stop here. The problem is who you are selling to, which no customer success hire will fix. Signs your hotel tech company has a retention problem helps separate a fit problem from a service problem.

• If churn is spread across segments you want to keep: go to question 5.

Question 5: Is there expansion you are not collecting?

Look at groups with one or two live properties, and customers using one product when you sell several.

• If there is clear expansion nobody is working: the hire pays for itself partly through growth, not just retention. Go to question 6 and weight the role towards account management.

• If there is little expansion available: go to question 6 and weight the role towards retention and onboarding quality.

Question 6: Can you give the role a clear number and a clear book?

A first customer success manager needs a defined set of accounts and one or two measures they own.

• If you can name the accounts, the retention target and the activation measure: hire.

• If you cannot: stop and define them first. A hire without a book and a number becomes whoever answers the phone.

The tree on one page

What the first hire should look like

• Hospitality background. Someone who has worked a front desk or run a department knows why staff turnover breaks adoption and is believed by general managers.

• Owns two numbers. Gross revenue retention for their book, and the share of new properties reaching first value on time.

• Owns the renewal calendar. Every renewal reviewed at least ninety days before the date, using a process like the one in building a renewal playbook for hotel software.

• Not the support queue. They can escalate and help, but tickets belong to support.

• Reports what they hear. A monthly note to product and sales on why properties stay, struggle or leave.

The takeaway

Hire your first customer success manager when properties reach first value and then drift, when support is not the bottleneck, when nobody can keep in regular contact with every account, when churn is spread across segments you want, and when you can hand the hire a defined book and two numbers. If you stop earlier in the tree, the money is better spent on onboarding, support or targeting.

If you are not sure whether your leak is activation or retention, the 12-point leak audit takes about twenty minutes and ranks demand, conversion, activation and retention on your own numbers.

Frequently Asked Questions