How to Accurately Plan CSM Headcount [+template]

Seth Dovev

At the end of 2021, the customer success department at Chili Piper was booming.

And let’s just say that going from four people to 19 in less than one year was no easy feat.

As we scaled, our team needed to forecast our continued headcount projections.

If any of you have ever tried forecasting headcount, you’ll know how difficult it is.

You have to factor in business projections, churn, and budget fluctuations throughout the year. And the stakes are high.

If you don’t plan CS capacity properly, you’re looking at either underutilized teams or customers being left behind. To solve this problem, I created our very own Customer Success Headcount Calculator — and I’ve been iterating on it over the past several months. (I shared my iteration process in this article).

This article shares the newest version of our headcount calculator, factoring in things we hadn’t thought of in the first round. Let’s get into it.

Where do you start?

Our customer success managers (CSMs) on the ground vocalized what they were experiencing regarding their time and productivity. But we needed the data to find an appropriate solution. 

We came up short in our initial search for data. Our CRM was not capturing time spent per customer or our CS tool. 

We continued to research what other SaaS companies have done, gathered internal feedback from our team, and dug into articles and communities to see what existing examples we could build from. 

From what we explored, CS headcount is typically modeled on revenue targets, as in, one person is targeted with turning $1M into $1.25M ARR. This supports the notion that customer success is an account management function. 

The moment the lightbulb went off

The problem for us was that this traditional headcount modeling did not align with our customer success organization and support model. 

As we prepared to share our initial findings and challenges with our Chief Customer Officer, we had an aha! moment.  

Why don’t we use Chili Piper to track CSMs’ productivity? 

Chili Piper’s customizable meeting types allow you to save time by pre-populating the calendar invite. The contents correspond to the existing sections of your calendar invites in Google or Outlook. 

If added to your Salesforce instance, Chili Piper will dynamically write a handful of custom fields to allow you to track and report on all your booking data directly in Salesforce. 

So now we had a trackable metric to start with (time spent per meeting type). 

We also knew we wanted to incorporate the utilization rate (hours worked/available hours). This would help gauge how much time our team was working with customers to understand and craft the optimal rate for our CSMs.

Here are the steps we took:

  1. Created a customer journey – We defined four distinct phases of our customer journey: Purchase, Onboard, Adopt, and Grow.

  2. Designed consistent and scalable customer experience– At Chili Piper, we strive to create a positive experience for all our customers throughout the customer journey, so we mapped out specific services and milestones our team would take the lead on no matter the customer size.

  3. Standardized meeting types in Chili Piper that tied to specifically defined touchpoints the customer journey – We focused on particular touchpoints throughout the onboarding and adoption phases that our team was responsible for owning no matter the customer size.

You might think … "But wait, isn’t there time preparing for and following up on each meeting type?” There sure is. So to capture those important time-based metrics, we gathered that intel directly from our CSMs. 

We found there were three areas our CSMs spent time during the onboarding phase of the customer journey:

  • Meetings– Measured by Chili Piper via SFDC

  • Prep-pre/post (PH, email, presentations) – Estimated by CSMs

  • Troubleshooting – Estimated by CSMs

We found there were four areas our CSMs spent time during the adoption phase of the customer journey:

  • # of supported accounts with meetings – Measured by Chili Piper via SFDC

  • # of meetings held – Measured by Chili Piper via SFDC

  • Amount of time held for meetings (hours) – Measured by Chili Piper via SFDC

  • Prep- pre/post (email/troubleshooting)– Estimated by CSMs

  1. We calculated the percentage of how many customers fell under each of our current customer segments (ENT, MM, SMB). This allowed us to get a weighted average of time spent for each customer segment within each customer journey phase.

Building the headcount calculator

With this new data we could create a dynamicheadcount calculator using an arsenal of data we capture via our CRM (SFDC) and from Chili Piper:

  • Current logos – CRM

  • Expected new logos – CRM

  • Expected ARR – CRM

  • Onboarding hours – Chili Piper

  • Total onboarding hours (onboarding hours * expected new logos) – Chili Piper

  • Adoption hours – Chili Piper

  • Total adoption hours (adoption hours * current logos) – Chili Piper

  • Working hours – Static

  • Growth hours – Static

  • Churn Prevention Hours – Static

  • Total Churn Prevention Hours

  • CS utilization %

  • Forecasted headcount 

Here’s how the Chili Piper CSM headcount calculator works

Step 1: Fill in your customer data in green

  • Current customers at the beginning of quarter

  • Expected new customers at the end of quarter

Step 2: Fill in your expected customer effort hours in light orange

  • The expected hours to onboard a customer to launch your product

  • The expected hours to help a customer adopt your product

Step 3: Fill in the % of working hours you want each team to dedicate to customers in orange

  • Working hours per employee presume a 40 hour work week and 13 weeks of work per quarter

  • Utilization should be no higher than 80% leaving 20% for personal development and passion projects

  • Avoid utilization >100% as it can lead to burnout/staff churn

  • Consider whether the team has sufficient coaching, enablement, tools, and processes to improve utilization

Using some Google Sheet magic built in this headcount calendar, I now run a few internal reports to input updated actuals for current logos, updated expected logos, and expected ARR every month.

I used to update every quarter, but I realized there was often a disconnect between expected and actual new logos — so I started running the numbers with actuals once a month to make sure we were predicting CSM headcount as accurately as possible.

I then present to the leadership team our current utilization percentage, where we need to be sustainable, and the forecasted headcount required to achieve success. Here’s a copy of the template so you can use it for your team!


Using Chili Pipers custom Meeting Types, we’ve created a more accurate estimation for H2 21 Headcount based on the average hours spent per customer depending on the customer journey stage they fall under. 

Tips for building your own CS-related headcount calculator 

  1. Understand your customer’s journey 

  2. Identify all relevant touchpoints your CS org is responsible for leading

  3. Standardize your meeting types. This will help you start tracking productivity across CS led initiatives.

  4. Use Chili Piper! Our products help across multiple departments (sales, marketing, support and CS), automate handoffs, and meeting scheduling. And you can use reports to track customer success managers’ productivity.

To all customer success executives out there, if you find that your CS organization doesn’t fit traditional headcount modeling, there’s a solution for you: Chili Piper. 

Not only will you have a data-driven approach to help quantify headcount needs, our inbound conversion platform will also give you all the tools you need to help scale your organization and give you time back to focus on driving value for your customers!

About the author
Seth Dovev

Seth Dovev is the Sr. Director of Customer Success at Chili Piper. He's passionate about managing our wonderful and growing Customer Success team, focused on providing all of our customers the best experience using Chili Piper. Connect with Seth on LinkedIn.

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