What’s Your Customer Success Hiring Strategy?

You’ve moved beyond the super early stages of your Customer Success team. You’re planning for the future. The company is growing quickly with aggressive sales targets this year.

How do you plan your hiring for Customer Success?

Sometimes Customer Success means “Customer Success Managers (CSMs)” but for many startups, it includes a range of roles: onboarding/implementation, technical support, professional services, and account managers (aka CSMs).

It’s a complex equation with nuanced variables. What’s the right number of people to hire and when do you bring them on?

Here are 6 factors to consider when planning your hiring and growth strategy for Customer Success.

6 Keys to Planning Your Customer Success Hiring

1. Understand the sales pipeline.

When deals get to the demo stage, how many are likely to close? Once you have a proposal sent to a customer, what % of those convert to new business?

The goal is to understand when new customers are (most likely) coming on board and what the impact will be to Customer Success.

Ways to track this:

• CRM dashboard
• Regular sync with Head of Sales
• List of what will likely close in 2-3 months
• Whatever is easiest for you and Sales

Make sure you have key information like:

• # of users
• dollar amount of the deal
• total number of new customers expected
• professional services quoted/complexity of implementation
• whatever metrics impact Customer Success workload

**BONUS** Keep an eye on the sales hiring.

Hiring sales reps directly impacts hitting sales targets. If there’s a big lift or lag in sales hiring, expect to see that downstream in a few months with customer count and Customer Success hiring.

2. Know your Customer-Success-to-Customers ratio.

How many customers or how much renewal revenue can one team member handle? If you have implementation separated from technical support, what are the ballpark ratios for each role?

Example:

An implementation specialist has 20-30 dedicated accounts they’re onboarding at a time, while a support team of 3 can handle tickets from 300 accounts.

A sales rep quota is 6 accounts per quarter so 1 implementation specialist per 4 sales reps is about right.

For support, add one support rep per 100 customers. If you have 15 sales reps each adding 6 customers per quarter, hire a new support person per quarter. This will be a moving target as the sales team grows.

Start with a guess - ahem - I mean, scientific hypothesis based on your unique business and customer. Adjust over time as you learn more.

Use the Customer-Success-to-Customer ratio plus the sales hiring, targets, and pipeline to estimate your team growth needs.

3. Always. Be. Recruiting.

Have you filled your open roles? Amazing! Keep having conversations with great candidates.

Be transparent that you’re not hiring now so you set expectations and build long term trust. Emphasize that you’re growing quickly, hiring will ramp again soon, and their resume looked great so you wanted to talk to them asap!

Things change pretty fast at a startup. You never know when you’ll need 10 people yesterday so keep the pipeline full.

4. When in doubt, underhire.

I’m not saying only have one person when you need 12. And definitely DO NOT scrimp or wait to hire Customer Success. (Saastr says so, too.) But if you’re not sure if you need 8 or 10, hold at 8.

When your team is a tad small, you can:

• pay bonuses for above and beyond effort or results
• hire contractors or virtual assistants to lighten the load
• let customers know there’s longer lead time for onboarding

If you hire to the max and sales numbers come up short, you are in layoff territory which sucks personally and for team morale. It’s way better to be stretched because of growth!

5. Think about efficiency and automation.

Building a great customer experience and Customer Success team is not just about the people. Continually evaluate repetitive or manual tasks. What could be automated? Should this be self-serve within the tool? Do we need to update our internal tools or documentation?

Examples:

Would customers buy more if they could upgrade within the app instead of going through an account manager?

Could Calendly save 30 minutes per day scheduling client meetings?

What about a Zapier Zap to push usage info to CRM so we can proactively reach out to at-risk accounts?

Keep a running list of ideas to improve your team’s output and efficiency, quantifying the time spent and revenue implications of improvements.

Then spend time thinking through or discussing the budget, time, and impact tradeoffs of different solutions. Some common approaches are:

• buy a tool
• internal or external engineering help
• people power (full time or contract)
• de-prioritize for now

Over time, your Customer-Success-to-Customer ratios should improve as you gain more efficiency and automation in your processes.

6. Contractors, Assistants, and Interns, Oh My!

If you have seasonal busyness or you need help today but aren’t sure of the long term picture, can you go with a more flexible option than a full-time hire?

Examples:

Your team is writing help articles and blogs → hire a part-time copywriter.

Making custom training slide decks for each client → engage a contractor or design freelancer.

Booking travel to client sites takes up several hours per week → outsource to a virtual assistant.

Updating metrics manually on a spreadsheet → Interns to the rescue. (Who will promptly figure out how to automate because they are smart like that! 🤯 )

I love this idea from Levels where “part of onboarding is finding a part of one's job and delegating it to a VA.”

Scaling a Customer Success team is both art and science. You’re looking at your company, team, customers, business economics, and trajectory, while juggling the day-to-day, and watching the chess board and pieces change constantly. There’s no perfect formula. It’s a fun process of tweaking and learning as you go.

What lessons or insights have been helpful as you’ve planned hiring and growth for Customer Success?