Most software companies solve a growth problem by hiring. Gaurav Agarwal solved one by doing less of that, not more.
Agarwal is President and Chief Operating Officer of ClickUp, where he oversees growth, sales, marketing, and retention at a company that, according to ClickUp, has reached hundreds of millions in annual recurring revenue, serves millions of users, and counts many Fortune 500 companies among its customers. He joined ClickUp as Chief Growth Officer in February 2022 before being promoted twice, first to Chief Operating Officer and then, roughly a month ago, to President. Four years ago, when he took over that side of the business, ClickUp was still building out its growth engine and looking for ways to scale more efficiently. His fix wasn’t a bigger team. It was AI and automation doing work that a bigger team used to do.
The math, by his own account, marked a recent promotion to President: revenue growing significantly over four years, customer acquisition costs substantially declining, and consistent performance against plan. “The whole game is feedback loops and automation,” he wrote in the post announcing the move. A separate account of roughly the same stretch, from an August 2025 episode of the GTMnow podcast, emphasized the role of culture and process changes, which Agarwal said accounted for a meaningful share of the improvement rather than simply spending less.
Either way, AI sits underneath most of it. In a September 2025 recap of his talk at SaaStr Annual, Agarwal said AI is now deeply embedded in roughly 80% of ClickUp’s revenue functions across growth and GTM, not as a support tool bolted onto the sales org but as a layer built into how the org actually works.
The floor AI removed
According to Agarwal, before AI and self-serve technology, a $50-a-month customer wasn’t profitable to serve well. He has explained that a rep costing the company $150,000 a year and managing 50 accounts needed thousands of dollars in yearly contract value just to break even. He argues that a well-built AI system can handle discovery, support, and basic account management for an SMB customer about as effectively as for a much larger account, at a fraction of the cost. That doesn’t just cut expenses. It opens up an entire tier of customers that ClickUp may not have profitably kept before.
He points to an AI system that can generate a pipeline worth millions of dollars each quarter and flag accounts showing early signs of churn, allowing a person to step in before the customer is gone rather than after. The same logic runs through ClickUp’s self-serve product experience, its community of millions of users, and its weekly webinars, which draw thousands of people each session. All of these create engagement using technology that helps them target the right customers who are raising their hands and want more help.
Right touches, not more
Companies hire humans to deliver many touches and then struggle to manage the resulting operational overhead. The instinct is to do more, without a clear understanding of what drives value. Agarwal argues that’s usually the wrong move. “More touches don’t win. Better-timed touches, at the right cost, do,” he wrote in a column on ClickUp’s go-to-market strategy published earlier this year. An account manager calling a customer who isn’t ready to expand doesn’t just waste an afternoon. It teaches customers to start screening calls from the company. However, calling to offer true value without any expectations can increase trust and goodwill with the customer.
Agarwal has built what he calls a portfolio of six customer touchpoints, ranging from free self-serve tools that cost ClickUp almost nothing, up through AI-driven outreach and community support, to high-touch human sales reserved for the moments that actually justify the expense: a signed contract, a usage spike that signals a customer is ready to grow, or a customer going quiet before they churn. According to Agarwal, moving a customer up that ladder, from the cheapest touch to a full one-on-one sales relationship, has significantly lifted ClickUp’s lifetime value per customer.
The bet underneath all of it is a plain one: growth is a systems problem before it’s a headcount problem, and many companies solve for the wrong variable. Taken together, ClickUp’s performance gives weight to Agarwal’s argument that growth can come from building better systems, not simply bigger teams.
Disclaimer: GeekWire newsroom and editorial staff were not involved in the creation of this content.
