“How did they do that? How did they get there?” Companies succeed because of the people who build them - operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game – building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next. 

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This month, we chatted with Cait Keohane, Chief Customer Officer at Airtable. As CCO, Cait leads the Customer Experience organization across Success, Support, Services, and Renewals, focused on driving adoption, expansion, and long-term customer value. Prior to Airtable, Cait spent more than a decade at Zendesk, where she helped scale the business from under $100M to over $1B in revenue. She held leadership roles across sales, operations, and customer experience, including leading the Customer Advocacy organization—a team uniquely positioned at the intersection of customer feedback, product innovation, and revenue growth. Throughout her career, her focus has remained constant: growing and protecting revenue, strengthening customer loyalty, and building exceptional customer engagement strategies that fuel business outcomes.

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1. You spent over a decade at Zendesk scaling the business from under $100M to over $1B in revenue. What's one lesson from that journey that fundamentally changed how you think about scaling customer organizations?

If there’s one lesson I took from Zendesk, it’s that scale is the most honest audit a company will ever experience. Growth has a way of making the invisible visible. It surfaces the strength of your leaders, the quality of your decisions, and whether your company truly puts customers at the center or simply markets that it does.

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That understanding has fundamentally shaped how I lead. I look for leaders who think beyond quick fixes and understand that heroics don’t scale. The ones who build strong, durable systems that support speed rather than slow it down. Leaders who solve for the long term, not just the problem of the day. I anchor decisions in data, and I continually bring teams back to the one constant that cuts through complexity: the customer’s voice.

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2. We’re big Airtable users over here at OpCo! What were some of your motivations for making the move from Zendesk to Airtable? What about the opportunity got you excited? 

I made the move to Airtable because I saw an opportunity to help shape the future of how modern companies operate. My years at Zendesk were incredibly meaningful. I grew up there professionally, learned what it takes to scale a category-defining business, and saw firsthand the impact the right tools can have on how teams work.

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One pattern kept showing up across companies: as organizations grow, work becomes fragmented. Information spreads across systems, processes become inconsistent, and leaders spend as much time stitching context together as driving the business forward. Airtable tackles that by combining structure and flexibility so teams can move fast and stay aligned. It's not just a tool—it's a foundational layer for how work flows and decisions get made.

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3. At Zendesk, you led Customer Advocacy—a function that sits at the intersection of customer feedback, product innovation, and revenue. That's a unique position. What's one thing you learned about translating customer voice into real business impact that some other leaders might miss?‍

Customer voice is most impactful when it brings clarity. Leaders need patterns, not anecdotes. When you translate thousands of signals into a clear view of opportunity and risk, customer insight stops being noise and starts driving action.

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And you don't need a fully engineered VOC program to get there. Most companies already have the raw inputs: support tickets, product usage data, customer sentiment, and conversations happening across the business. The key is synthesizing those into themes that inform real decisions and folding them into everyday workflows so customer understanding becomes part of how the company operates.

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The most effective organizations treat customer insight as a strategic input, not an afterthought. When it's embedded into product decisions, go-to-market planning, and operational priorities, it becomes a competitive advantage.

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4. You've moved between sales, operations, and customer experience throughout your career. How has that cross-functional perspective shaped how you run customer organizations differently than leaders who've stayed in a single lane?

The biggest advantage is I can translate between what sales promises, what product builds, what operations can deliver, and what customers actually need. Most CS leaders who've only done CS optimize for customer happiness in isolation. I optimize for sustainable customer outcomes, which means sometimes pushing back on sales deals that won't succeed, bringing customer insights that inform product innovation and business strategy, or working with ops to fix root causes instead of just smoothing over symptoms. I've been on the other side of those conversations, so I know how to make them productive instead of adversarial.

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5. The Chief Customer Officer role has evolved significantly. Some CCOs are still fighting for a seat at the revenue table, while others are driving business transformation. How do you define the role today, and what's your take on where it's headed?

This is such a good question, and I have strong views on this!

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We used to think about the customer journey in two phases: sales gets them in the door, CS keeps them from leaving. That's fundamentally the wrong way to think about it now. The fastest path to revenue is growing the customers you already have. Retention and expansion are the business model now.

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With that in mind, I see the leaders of CS becoming the most strategic operators in the business. We have the most critical insights: what makes customers stay, what makes them grow, where the market is moving.

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I believe that companies that don't put CS at the revenue table are going to lose. Treating CS like a cost center isn't just outdated thinking; it's a competitive disadvantage that will only widen over time.

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6. What's one counterintuitive or unconventional approach you've taken in building customer experience organizations that's paid off in ways that surprised you?

At Zendesk, I deliberately overstaffed ops. Most CX orgs have lots of agents and a thin ops layer. I flipped that and invested heavily in operations: people who build workflows, fix processes, and eliminate friction before it reaches customers. 

It feels backwards, but well-resourced ops dramatically reduces how many frontline people you need. They eliminate repeat contacts and fix root causes. The math works fast.The surprise wasn't just efficiency. It was what happened to the frontline team. When ops handles the foundation, customer-facing people stop being ticket-takers and become problem-solvers. Morale and retention improved while headcount stayed flat. The foundation layer isn't overhead. It's the highest-ROI investment in CX.

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7. What's your approach to AI transformation in customer experience, and what are some of the ways Airtable is specifically using AI to transform its own operations?

We're pursuing AI transformation on two fronts. First, we've fundamentally reimagined how we serve customers across the entire customer experience organization. We've evolved from traditional customer success to what I call technical success, recognizing that in an AI-native era, customers need technical fluency, strategic guidance, and change management support. But it's not just customer success. We're rethinking AI-human handoffs in support, reimagining enablement strategies, and equipping our ecosystem of partners to enable AI adoption across our customer base.

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Second, we're embedding AI throughout our own operations. We use AI for early risk detection and sentiment analysis to surface issues before they escalate. We leverage customer intelligence tools like Common Room to track engagement signals at scale and have built custom apps for bug tracking and insight aggregation. This allows our team to operate strategically: AI handles pattern recognition and data synthesis while our people focus on complex problem-solving.

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8. What's the best advice you've received—or given—about how to manage people?

The best advice I have ever received is that your team will rise to the level of your clarity and fall to the level of your inconsistency.

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People do not need perfection, but they do need a leader who is steady, transparent, and predictable in how they make decisions.

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The advice I give most often is to create an environment where people know what great looks like and feel safe enough to run toward it.

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9. What's a piece of advice you would give to yourself 10 years ago, if you had the opportunity?

Lean into uncertainty, and build time for reflection.

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Early in my career, I craved clear paths and defined roles. But the most meaningful growth and the most interesting opportunities came from leaning into uncertainty and building something new. Whether it's creating a new function, driving a strategic pivot, or leading through transformation, the discomfort of ambiguity is where real impact happens.

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The second piece is more subtle but equally important. I was always saying yes to projects, stretch assignments, and opportunities, and that served me well. But there came a point where I had to make a critical decision about what was next, and I wasn't sure. I'd been so focused on executing what was in front of me that I hadn't been intentional about where I was heading. Regular reflection creates clarity when you need to make those pivotal career decisions. Being deliberate about your narrative gives you agency in shaping your path rather than just responding to what comes your way.