Rachel Provan, former Director of Customer Success at Doodle and now a CS leadership coach, shares hard-earned lessons from building and scaling Customer Success teams from scratch — three times over. 

“No one teaches you how to be a CS leader. It’s an entirely different job than being a CSM. A lot of CSMs who are just put in the position of a CS leader end up failing. It’s incredibly unfair.” 

When Rachel Provan stepped into her first role as CS leader (at Arago, back in 2017), she felt utterly clueless. While she’d excelled as a CSM, she now found herself scrambling to stay on top of everything. “The strategies I’d seen on webinars were suddenly much tougher to put into practice than they seemed.” 

Rachel figured it out — then went on to build and scale two more CS teams from the ground up, first at Fidelus, and later at Doodle, which she joined just as the pandemic was driving a massive surge in demand.

Today, Rachel is a customer success leadership coach, helping CS leaders and early-stage companies avoid feeling the helpless sense of overwhelm she once felt. 

Here, she shares her top tips for when to hire your first CS person, how to scale without burning people out, and why most churn problems start during onboarding.

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Here are Rachel’s top takeaways for new CS leaders 

• Don’t get stuck in a player-coach role. You need to think strategically, not get stuck in the weeds with the rest of your team. 
• CS teams can’t be proactive without tooling and headcount. No CSM should be supporting more than 50 accounts.
• Bad onboarding = churn. Make sure you’re asking the right questions. And get your customer to define their own quick wins and success metrics.
• Live training is expensive and ineffective. Drip-feed training in multiple modalities instead. 
• Renewal decisions don’t happen at renewal time. Your customer made the decision to renew or churn months ago. Track outcomes early and check in at the six-month mark.

How to build a customer success team from scratch 

Say you’re talking to an early-stage founder or GTM lead. They’re thinking about building out a CS function, but they aren’t sure if it’s the right time or if you’re the right hire. 

Here’s exactly what to tell them, based on Rachel’s 15 years of experience: 

When should you start building a CS function?  

There are two indicators that it’s time to hire, at a minimum, a support rep, says Rachel: 

1. The founder is getting buried under customer queries. 

As soon as dealing with customers is “preventing you as a founder or CEO from improving your product, making more money, when it's slowing down your growth,” it’s time to hire. 

2. Customers aren’t getting to value without help. 

The whole point of CS is to help customers reach their goals with your products. If you have a fairly self-evident product, chances are that 70% of your customers will figure it out on their own. But there’s usually around 30% who’ll need a bit more hand-holding — and once that starts happening, you need CS. 

Should you focus on Support or Success? 

It depends on what the company needs. Support tends to be reactive and ticket-based, and Success is usually more proactive and strategy-focused. 

Generally, most companies should start with Support, and then split the roles into Support and Success as they mature. 

Rachel has a handy rule of thumb here: 

• When dealing with customers is slowing down growth, it’s time to hire a Customer Support rep. 
• When you need someone who’ll be more strategic about encouraging renewals, or when customers are starting to need in-depth support, you need a Customer Success Manager. 
• Each CSM should be handling 20-50 accounts. Once you’re past that point, you’re either going to need to invest in tools or hire another CSM. 

What makes someone the right fit for a CS leadership role? 

At the point where you’re growing a CS function, many founders assume they’ll need to hire someone to lead the team. But Rachel believes that a strong CSM can often be the right fit for a leadership role — especially if they’ve been there from early on, have risen quickly, and clearly understand the strategic value of CS beyond just support. 

Plus, they’ll likely be taking on a player-coach role, particularly at the beginning, so it makes sense to promote internally. That said, this needs to be a temporary situation. As Rachel puts it:

 “You cannot manage accounts and build strategy at the same time. One requires an in-the-weeds view, and one requires a higher, more strategic view.”

So make sure that the CS leader has time for strategic thought, not just fire-fighting — or you’ll be tying their hands behind their back. 

Tips for scaling up a high-performing CS team 

Leading CS at Doodle gave Rachel a close look at how to grow and mature a CS function in a rapidly scaling business. Here are her tips for keeping performance high without burning out your CSMs: 

Be realistic about what stage you’re at 

Many CS leaders find themselves under pressure to be “proactive.” But, without the right tooling and data, that’s simply not realistic, says Rachel. 

“There are steps to a maturity model of CS It goes: 

• Reactive
• Informed
• Proactive
• Predictive 

“The reactive is: we don't have any data coming to us, so we just take what comes at us. Informed is when you start to get some data and systems in place. But you've got to be willing to spend the money on that and the bodies and the time to set it up.” 

In other words, if you’ve got a single CSM managing over 100 accounts in a spreadsheet, there’s simply no way for them to be proactive. 

If you don’t have the budget for CS tech yet, it may make sense to segment your customers. While a CSM can’t be proactive about renewals and upsells across all your customer base,  they could probably take a more strategic approach with a smaller handful of accounts — say, your top 20 customers. 

Renewals should be a formality 

“CSMs, early in their career, tend to think that customers decide about renewing at renewal time. No, that decision was made on a random Tuesday after some interaction they had with your product, where it either got them the result that they wanted or failed miserably.” 

Rachel’s advice is to think of renewals as being like performance reviews — there shouldn’t be any surprises, it should be almost a formality. 

That only happens if you're consistently tracking progress and addressing issues long before the contract is up. 

Rachel recommends sending a simple check-in survey around the six-month mark: “You said you wanted to achieve X with our product. Have you achieved that?” Based on the answer, you’ll know whether to intervene or move into expansion conversations.

Avoid churn by nailing onboarding 

Bad onboarding means early churn, says Rachel. “Onboarding is not done when you've said, ‘Here's how to use the project. Okay. Bye. Good luck.’ Onboarding is done when they are "on board," when they see value.” 

Here are a few tips to get this right: 

Get customers to define their own “Aha” moment. The most important onboarding question to ask is: “What would be an early indication that things are moving in the right direction?” By inviting customers to tell you what a quick win would be, you make it far more likely that they’ll notice it when it happens. 

Understand their metrics. You also need to make sure you know how customers are measuring the value you provide, so you can do those on-going check-ins that improve renewal rates. Rachel recommends asking the following: 

• What are you looking to achieve with our product? 
• How do you measure that? 
• Where is it now? 
• Where do you want it to be? 

Skip the live training.

‍“Live training is expensive and time-consuming. And it's not necessarily better,” warns Rachel. “You can have the sense that people are there, and therefore they're definitely going to get trained because their butt has to be in the seat. But can you tell if they're reading their email during training? Because I can't.” 

Drip-feed training instead. Part of the problem with live training is that it often doesn’t stick. “We forget 90% of any trainings or any instructional stuff within 24 hours. But people don't like to be like, 'Hi, I completely forgot what you told me yesterday, and I now don't know what I'm doing.'”

Instead, you’re better off breaking training down into bite-sized content across formats — videos, screenshots, in-app guides. That way, you make it easy and give attendees a quick win that will make them more likely to come back for more. 

Set clear boundaries with Sales 

Rachel doesn’t believe CS should be running pre-sales demos: “That’s a hard no. ”Trying to split ownership muddies accountability and risks overwhelming your team. 

Instead, create a clear but simple sales-to-success handoff. You can’t expect Sales to put together a three-page document for every account they hand over to you — and you don’t really need one. Instead, ask them to brief you on the essentials:

• Who are the key players? 
• What are they trying to achieve? 
• Is there anything they hate? 
• Any red flags?
• Is there anything really different in the contract I need to know about?

This context should be enough for you to step in confidently and support the customer from day one.

Handle pivots and price increases with finesse 

If you’re in CS for a startup, you’re going to be the one telling existing customers that prices are changing, or that you’re not offering that feature they like anymore. Chances are, they won’t be happy — but there’s a right way and a wrong way to handle it. 

For price increases, communication and lead time are everything. Give loyal customers 6–12 months’ notice and a gradual ramp-up. Clearly explain what’s changed and why the price is going up. Done well, this transparency “tends to cushion the blow [and] make a lot more people stay,” says Rachel. 

And, if you’re pivoting dramatically or making a major pricing change, make sure you’ve removed those accounts from CS targets to avoid demoralizing the team. 

Watch out for burnout 

Burnout is a serious risk for CSMs, and as a CS leader, it’s your responsibility to keep an eye out for it. The problem, Rachel explains, is that “CSMs want to help so badly. They're people pleasers, and they will burn themselves out. They will work till eight o'clock, nine o'clock, and not tell you they're doing it.”  

She has two practical suggestions here: 

• Check in frequently. Ask your team about their account load. Listen when they tell you they’re at capacity. Check their calendars for the number of kickoff meetings they’re attending. 
• Consider hiring a CS admin assistant to handle low-priority tasks.  “Should I be paying someone $60 an hour, $50 an hour to do a $10 an hour task? No. So, stop giving them $10 an hour tasks. Pay someone who makes a lower rate to do more of that administrative work, and you will get much more strategic CSMs who will be able to handle a lot more accounts and actually move those accounts forward and get more out of them.” 

Watch the full episode

Want more insights into becoming a better CS leader? Watch Rachel’s full conversation with Alex Krakov on Grow & Tell, Dock's podcast for revenue leaders.

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