Hey {{first_name | CS Pro}},

Ever wonder how a team of 12 supports 12,000 customers without drowning? This week I sat down with Andrea Kale, Chief Revenue Officer at Help Scout, who pulled off a full resegmentation of that exact base with a nimble crew.

She came up through marketing as a CMO before taking on the full revenue remit, so she sees the post-sales side differently than most revenue leaders. We got into how she tiered her customers, why she thinks product should own churn, and how support became one of her biggest revenue drivers. Let's get into it.

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Andrea said something she admitted was controversial: the churn target should sit with the product team, not customer success. Her reasoning is simple.

At HelpScout, that's not usually a problem. Their stats show you can get up and running in 15 minutes and be a power user in a day. Because the product just works, the questions her team has to answer don't overwhelm the queue.

She uses something called the ARPA framework, accountable, responsible, participant, advisor, to decide who owns what, and for the churn number, she puts the accountability on product. Her advice for anyone interviewing at a company?

Ask what their gross retention rate is, because that one number tells you whether customers are voting with their dollars.

With 12,000 customers and only 12 people, serving everyone the same way was never going to work. So Andrea and her team broke the base into four tiers by ARR, then layered on two overlays: white space, which is expansion opportunity from customers not yet using a product, and product health, which is adoption gaps where customers aren't getting full value.

The interesting part is how they did the analysis. Their data team connected every data point they have, from product usage to Salesforce to HubSpot, through a tool called Hex. From there, they could query all of it with Claude.

Andrea would prompt it with things like:

and it would surface how much revenue was sitting inside each tier and how to staff against it. She called it "an analyst in my pocket." If you're starting from scratch, her advice is to pick the variable you'll tier by first, get all your data connected, then prompt your way toward the natural splits.

Here's the part I didn't see coming. At Help Scout, 30% of new revenue comes from referrals, and Andrea traces that directly back to the support team.

When new customers tell her they were referred by a friend or colleague, it's because the support experience was that good. Her team is thorough, kind, funny, and technical when it needs to be, and that becomes a differentiator people actually talk about.

This doesn't mean they've sworn off AI. Their product, AI Answers, handles the basic questions like password resets, so the humans can focus on the complex, account-specific problems where they add real value. She calls it "no dead ends." If the AI can't answer, customers are immediately given the option to connect with a human.

Andrea compared it to Excel and accountants. The tool accelerated the work, it didn't replace the people. AI first works right up until it doesn't, and then it's a human to the rescue.

This week, pick your middle tier of customers, the ones who aren't your biggest accounts but aren't your smallest either, and run a white space analysis on just that group. Andrea pointed out that a lot of hidden revenue lives in that middle chunk, but most CS teams are too time poor to dig in. Pull your product usage data, look for who isn't using a feature or product they'd clearly benefit from, and pick three accounts to bring a real expansion conversation to. You don't need a fancy data stack to start. Even a simple prompt with the data you already have can point you toward the opportunities sitting right in front of you.

That's it for this week. If you want all of Andrea's insights, including how she thinks about the forward deployed engineer mindset for CSMs, have a listen on Spotify, Apple Podcasts, or YouTube, and let me know what you think.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,
Anika