At Setuply, we see client success as the thread that connects onboarding to sustainable growth. Few people understand that continuum better than John Gleeson.
As the founder of SuccessVP, John partners with early-stage founders to build client success motion before the first CSM is even hired. His journey started far from Silicon Valley—in a small Canadian town, through the frontlines of startup sales, and into the C-Suite of a hypergrowth SaaS company. John’s perspective is rooted in experience, insight, and an unmistakable passion for helping companies scale with purpose.
In this post, we’re thrilled to hand the mic to John to share his story—and his take on where client success is heading.
My entrance into the software world came through an unexpected door: a lean startup class at my university in Nova Scotia—one of only four North American schools offering it at the time. The lightbulb clicked on instantly. I’d been an entrepreneur at heart for as long as I could remember, but this was different. This was about testing, iterating, and building with purpose. From that moment, I knew I had to find my way to Silicon Valley.
I co-founded a startup in that class; it didn’t exactly take off, but it did open a meaningful door. I became the first hire at a new venture that relocated to New York City. With no product and no revenue, my initial job was to find product-market fit and land the first deals.
Eventually, I helped that company hit its first $1M in ARR, transitioned into the first customer success manager role, and found myself managing everything from onboarding to renewals. That hands-on, all-hats-on-deck experience taught me what it really takes to grow post-sale.
That journey took me to a fast-scaling company called KeepTruckin (now Motive), where I was fortunate to see what client success looks like at scale—from $1M to over $300M in ARR, supporting 130,000+ clients. But growth doesn’t come easy, especially in client-facing functions.
As companies scale, their margin for error shrinks. It’s not enough to sell the vision: You have to operationalize value delivery. For me, that meant building not only systems and playbooks, but a network of mentors and C-suite peers to help me keep pace with the company’s growth. The meetup community I helped grow became my cheat code—an advisory board I could call on for every blind spot, pivot, and challenge.
Through that network, I kept meeting early-stage founders. Beyond advice, they were looking for someone who could see the whole journey, from first sale to lasting value. That’s when I realized the gap: founders are often left to “wing it” when it comes to client success until much later than they should.
That insight led me to start Success Venture Partners, a venture firm purpose-built to help founders lead client success. We help them get the early playbooks right—because in B2B SaaS, the sale is just the start. The real work begins after the contract is signed.
Today, client success isn’t just about renewals—it’s about resilience. With AI accelerating innovation, the pace of competition is faster than ever. The traditional value props that worked a year ago might not even register these days. And while AI automates the “busy work,” it also forces companies to rethink how they demonstrate differentiated value.
We’re seeing this pressure drive client success into new territory. In some companies, it’s being folded under revenue leadership; in others, it’s merging into operations. The Chief Client Officer (CCO) title is emerging, but it’s not yet standard across the board. The post-onboarding lifecycle is becoming more complex, nuanced, and central to sustainable growth.
AI can help with that complexity—summarizing calls, surfacing insights, automating follow-ups—but it also demands more from your product and people. When every company has access to the same tools, your edge becomes how you use them and who you put in charge of the relationship.
As AI reshapes workflows, the one thing it can’t replicate is the nuance of human connection. The value of a meaningful conversation, a creative solution brainstormed in real time, or the trust built through years of collaboration—that’s where the future of client success lives.
At SuccessVP, we believe that founders don’t need to wait to operationalize this mindset. If anything, embedding strong client success early is how you build companies that last. When the only constant is change, adaptability, empathy, and execution become your most reliable tools.
Thank you, John, for sharing your journey and your vision for the future of client success! As AI reshapes the speed and scale of business, your message is a critical reminder: success is sustained through intention. At Setuply, we believe the future belongs to companies that invest early, stay close to their clients, and adapt faster than the market moves. Your story shows what’s possible when we treat client success not as a department, but as an overall philosophy.