How To Scale Customer Success

Summer Jowett (CS Leader at Tricentis), Dan Ennis (Director of Commercial CS at Workato, former Scale Leader at Monday.com) and Lane Holt (Director of Growth at Constant Contact, former Director of CX and Scale Programs at Gainsight) left to right

If you’re in Customer Success and thinking about how to scale your efforts, you’re not alone. I joined a panel with Summer Jowett and Lane Holt for a conversation all about digital CS strategies. It was one of those rare discussions where everyone’s experience aligned but still brought a fresh perspective.

If you are a visual learner, scroll down to watch the full session on YouTube. Otherwise, check out my key takeaways from the session in this blog post.

My journey into digital CS started back at my first SaaS company, before I joined Monday.com. 

We sold to insurance brokers at the enterprise level, but the real users, the ones who needed to understand and adopt the product, were the clients of those brokers. We're talking about hundreds or even thousands of businesses for every contract. We couldn't possibly meet them all one-on-one. 

So from day one, we had to figure out how to drive engagement and adoption at scale. That’s when it clicked for me: Digital CS isn't just for the long tail; it's a core strategy that benefits all customer segments.

At Monday, this same thinking helped us build scalable programs that accelerate growth and deepen product usage, no matter the customer’s size.

Lane shared a similar realization from her time at Gainsight. During the SaaS boom around late 2020, her team was growing fast but couldn’t justify adding more headcount to support the customer influx. They needed a smarter solution. They leaned into digital motions and shifted from their traditionally white-glove CS approach to building out tech touch strategies.

Gainsight customers were also asking how to do digital better, so the team had to lead by example and become the benchmark. I really appreciated how Lane framed this not just as a business necessity but as an opportunity to reimagine what CS could be.

Summer’s story bridged both of ours. She was supporting a customer base in the six-figure range, many of whom came in at lower price points and couldn’t be covered through traditional headcount. Her team had to create digital programs just to close the gap, and in doing so, they found that the solutions benefited everyone. What started as a workaround became a better experience across the board.

When we talked about which channels worked best, we were all on the same page: it’s not about doing everything everywhere, it’s about meeting customers where they are. Some customers live in email, others in the product. Some want self-serve, others want a community.

Lane made a great distinction between multi-channel and omnichannel. Multi-channel is blasting the same message everywhere. Omnichannel is about knowing what message to send, where, and to whom, based on the goal you're trying to accomplish.

That approach resonated with me deeply. I’ve always found it more effective to start with the desired outcome, identify the persona, and then choose the right channel: email, in-app, community, chatbot, whatever it might be.

That led us into a conversation about the “pooled” CSM model, which I’ve led in various forms. The idea is to have a team available for inbound requests and short-term engagements. But for it to work, there has to be ownership. 

Lane nailed this. 

At Gainsight, each pooled CSM managed a strategic initiative, like office hours or digital business reviews, so they weren’t just reacting, they were building programs. That feedback loop from CSM to digital team allowed them to scale smarter and stay ahead of recurring customer needs. We did something similar on Monday. We assigned ownership behind the scenes so CSMs could lead proactive efforts even if the customer didn’t know who was assigned to their account. It made the experience feel personal, even at scale.

We also talked about personalization. None of us believed in a one-size-fits-all approach. It’s essential that digital touchpoints feel intentional. Customers shouldn’t know, or care, that they’re in a “digital” segment. 

Summer put it best: never let a customer feel like they’re getting less because they’re not in a high-touch program. Anyone could be your biggest customer next year. The experience should reflect that.

When we shifted to talking about the roles needed to make all of this work, I shared how I think less about job titles and more about capabilities. The best hires in digital CS have a mix of data fluency, CS strategy, and marketing chops. They can identify patterns, design solutions, and then measure their effectiveness. 

Lane and Summer echoed this. 

Whether the person is called a program manager or a journey orchestrator or a scaled CSM doesn’t matter as much as what they’re actually doing and the impact they’re delivering. Passion also plays a big role. Building digital programs requires creativity and resilience, especially when resources are thin.

As a team grows, the structure evolves. Lane described her pod model at Gainsight, which includes a program manager, an in-app designer, an orchestrator, and an events person working together. It started lean and expanded as the program proved its value. Summer talked about how different teams like marketing, ops, CS often own parts of digital CS depending on the company’s maturity. 

The key is collaboration. And I fully agree. Early on, you don’t need to own everything. Focus on proving the value of what you do own and let that open doors.

We closed out the conversation by talking about how to get started. 

My advice? 

Strengthen what you already have. Don’t try to rebuild everything at once. Choose one motion that can be digitized liker office hours, or a monthly email. Lane added a great framework: use a two-by-two to map impact vs. effort. Knock out the high-impact, low-effort wins first. Summer emphasized mapping the customer journey and identifying pain points that digital CS can address. Her point stuck with me: don’t just solve problems, solve the right ones, based on your skills, resources, and passion.

This webinar reminded me just how far digital CS has come and how much opportunity still lies ahead. Whether you're just starting out or scaling a mature program, the same principle applies: keep the customer at the center, lead with outcomes, and build with intention.

Watch the full session on YouTube and remember to pay it forward by sharing with anyone in your network who might find this useful.

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