Planning for 2025: Team Structure

By Kristen Hayer

Welcome to part 3 in my series on Planning for 2025. Knowing how you want to structure your team is foundational to preparing your budget for the coming year. However, to effectively budget, you need to have segmented your customer base and planned journeys for each segment. If you haven’t done that yet, take a look at last week’s article and review the steps.

People are usually the most expensive line item on a customer success leader’s budget, followed closely by the technology those people need in order to be effective in their roles. This week, I’ll be focusing on how to dial in your headcount for 2025, based on the customer journey you expect your teams to deliver. Here’s our approach to planning your team:

1. Determine Your Functional Teams

Different CS teams include various functions. Some include only the role of CSM. Others include a broad array of roles including Onboarding specialists, Support roles, Services teams, and other customer-facing jobs. For your team, think about the roles that make sense given the customer journeys you planned, the expectations of your customer base, and the maturity level of your company. Early-stage startups might only have the role of CSM, whereas mature companies may have 20 or more different teams serving customers. Write down the teams and roles that make sense for your team in 2025.

2. Calculate Time to Deliver Each Journey by Role

Estimate how long it will take to deliver your planned customer journey on a per-customer basis for each role. This should vary by segment. For example, if you have a CSM team delivering a journey to an SMB customer segment, you might estimate that a monthly meeting and quarterly business review will take your CSMs 2 hours per customer per month. On top of that, you might also have a support team who spends on average, 15 minutes per customer per month. If you just planned out your customer journeys for the first time, you would need to make an educated guess about how long things take, which is fine. If you have real data, even better!

3. Develop Bottom-Up Customer Ratios

Now, for each customer-facing role you’ll need to calculate how many customers that role can manage. You can do this by dividing the available time for each role by the number of hours it will take to deliver the customer journey you planned. Using my previous example, if a CSM has 120 hours per month available, and it takes 2 hours per customer per month to deliver the customer journey, they can each handle 60 customers. Note: I didn’t use 160 hours, even though that is the equivalent of 4, 40-hour weeks. That is because these are humans, not robots! They take breaks, have internal activities they need to do, attend meetings, and go on vacation. Use a reasonable percentage of the total hours available to do this calculation.

4. Gather Benchmarks and Adjust

Now that you have a customer/teammate ratio, compare that to normal benchmarks for each role. I’m sure you’ve probably run across the benchmark that a CSM should represent $2-5 million in revenue, or that Support and Services teams should represent 10-20% of a company’s revenue. For each role, do some research on benchmarks, or ask your finance leader for the benchmark they prefer to use. Use that benchmark to back into a top-down customer/teammate ratio. For example, if you decide that each of your CSMs should represent $2 million in revenue and your average customer brings in $35k/year, then your CSMs should each have 57 customers. That’s close to your bottom calculation – great job! I’ll talk about what to do if there isn’t a match in a minute…

5. Evaluate Management and Operations Needs

Once you have your customer/teammate ratios sorted out and you use those to plan your front-line staffing needs for 2025, you need to also consider both managers and operations team members. A good rule of thumb for managers is that for each 4-12 people on the team, you need a people manager. Newer leaders can handle roughly 4-5 direct reports, while seasoned managers can handle up to 12. Operations is a bit more flexible. Consider the tasks you need to cover on your team. Do you need someone to administer your CRM system or CS platform? Do you need analytics help? Is your team large enough to need a dedicated educator? Be sure to build these operations roles into your team.

While this may sound simple, in practice there are some things that can complicate building out your team structure. Here are the things we frequently run into when evaluating our customers’ headcount plans, and what we do about them. So, what if…

• Your Benchmarks Don’t Match Your Bottom-Up Plan?

When we see this, the typical issue is that the benchmark indicates a CS role can handle far more customers than the journey indicates they can. Using my previous example, let’s say instead of an average of $35k/year, your customers bring in $15k/year. This would make it look like a CSM could manage 133 customers instead of 57. That is a huge difference and obviously doesn’t align with 2 hours/customer/month. When this happens you either need to revisit your customer journey and trim it down or evaluate the benchmark and trim that down. A candid conversation with your finance person is probably a good place to start discussing these tradeoffs.

• You Don’t Have a Big Enough Company for Different Roles?

In many cases this is appropriate, and it just makes your planning job easier! However, if you have the sense that your team is stretched thin in terms of the volume of tasks on their plate, it may be worth considering splitting your group up. In our experience, a single role can typically handle 30 unique tasks (responding to customer emails, business reviews, escalations, success planning sessions, etc.) before the role starts to become too overwhelming. Even a relatively small team may benefit from being split into two parts to make things more efficient.

• You Get Pushback from Finance or HR?

Sometimes Finance and HR teams have set ideas about how specific roles should function, which benchmarks to use, or how many people they want to see on your team. Often, you won’t agree with their perspective since you are closer to the actual work. When you need to make the case for your planned team structure, be sure to go to them with facts and data instead of emotional pleas that you’re your team feels “stretched thin”. Building a model like I’ve described above and having numbers behind your staffing plan, allow you to confidently have a conversation with your finance and HR leaders about the tradeoffs you will face if they require adjustments to your model.

Later in this series of articles on planning I’ll cover how to build a business case for more budget. Building a staffing model like this is the first step toward ensuring that business case will be given serious consideration.

Good luck with your 2025 planning!

Want to know the trend on CS headcount? Check out this amazing Customer Success Leadership Study. It captures insights of more than 1,000 CS Leaders globally on the definitive picture of CS team sizes, budgets, reporting structure, tech stacks, and more, with valuable insights into goals, challenges and best practices.

Do you need help planning your team structure? We have a class for that! The Success League is a Customer Success consulting firm that also offers a robust CS Leadership training program. Visit TheSuccessLeague.io for more info or to contact us.

Kristen Hayer - Kristen founded The Success League in 2015 and currently serves as the company's CEO. Over the past 25 years Kristen has been a success, sales, and marketing executive, primarily working with scaling tech companies, and leading several award-winning customer success teams. She has written over 100 articles on customer success, and is the host of 3 podcasts about the field. Kristen has served as a judge for the Customer Success Excellence awards, and is on the board of several early-stage tech companies. She received her MBA from the University of Washington in Seattle, and now lives in San Francisco.