Don’t be surprised if Zendesk CEO, Tom Eggemeier, calls you

In Leaders in Learning, we sit down with industry leaders and explore their lives and experiences to uncover the learning principles, key moments, and common threads that shape careers, businesses, and journeys. Through these collective stories, we'll piece together the bigger picture of what it means to be a leader in learning.

Zendesk CEO, Tom Eggemeier built his career on two things: A willingness to take risks and an unwavering focus on customers. Growing up around his grandparents’ grocery store in a small Kentucky town, he saw firsthand how knowing people personally and serving them well could build trust. That experience shaped his leadership philosophy: Treat people the way you’d want to be treated.

In this episode of Leaders in Learning, Tom shares how customer obsession, AI, disruption, and authenticity guide his approach to leadership and innovation—and why we should never lose sight of the human at the other end. 

Catch the full conversation to hear how Tom connects small-town grocery lessons to the future of AI. Or, if you’re short on time, skim the key takeaways here.

Back to the corner store: The future of CX

TL;DR: Customer obsession is a mindset Tom inherited from his grandparents’ grocery store, where knowing your customers personally and fixing mistakes fast was the best way to build trust.

Tom likes to joke that in Silicon Valley, he often gets “accused of being Midwest nice.” He can’t help it. Growing up in Dayton, Ohio, with deep family ties in Covington, Kentucky, those roots shape how he leads today. He spent his childhood watching his grandparents run a small-town corner grocery store where every customer mattered.

“My grandparents really knew all their customers,” he recalls. “It always amazed me,” adding that anytime someone walked in, his grandparents knew their names—and even their sandwich order. That kind of service left a mark. For Tom, it wasn’t just about selling something; it was about building something: Trust. And they did it one interaction at a time.

Fast forward to today, and that ethos shows up in how he leads Zendesk. Tom takes around 1,000 customer calls a year, “no matter how big [or small] the customers are.” It doesn’t matter whether someone spends $240 or $10 million, he truly believes “every customer is important.” 

Sometimes people are shocked it’s really him on the other end of the line. But for Tom, customer feedback is paramount. It’s the first thing he thinks about every morning, prioritizing negative sentiment so he can fix issues fast. (That lesson comes straight from his grandparents’ grocery store: When you make a mistake, own it and make it right.)

“Treat customers like you’d want to be treated yourself. When you make mistakes, just own up to it and try to make it right as quick as possible.”

But scaling a $2B company hasn’t always made that easy.

Tom acknowledges that, for a while, growth caused Zendesk to drift from its customer-obsessed roots, limiting contact to messaging alone. But Tom is steering the company back—reopening phone, email, and live channels—because giving customers what they want sometimes means giving them more than one way to be heard. The goal isn’t closing tickets; it’s earning trust. 

The principles of true customer obsession:

• Treat every customer like the only customer: Whether they spend $240 or $10M, every interaction deserves the same personalized care and attention.
• Meet people where they are: Listen to your customers, and connect the way they prefer—phone, email, chat.
• Fix it right, not just fast: Speed matters, but what matters more is owning mistakes and closing the loop on root causes, not just cases.

Right now, what excites Tom most is how data and AI are helping companies get back to his grandparents’ level of customer service, only this time at massive scale. “We’re in an era where we’re actually getting back to the corner grocery store of the 1950s.”

AI-first, human always

TL;DR: The future is about giving customers options: Instant AI when they want it, and human connection when they need it.

Under Tom’s leadership, Zendesk has embraced a simple mantra: The customer is always human. He’s quick to admit the future is changing fast: Within five years, “over 80% of customer interactions” could be handled by AI agents, and in half of cases, customers will bring their own AI agents too.

That doesn’t mean the human element disappears. Quite the opposite. In his view, AI should make things faster, more personal, and easier to predict, while still leaving room for people to choose how they engage. 

“I think you can make AI very human-centric and human-first. AI can be empathetic." 

Choice makes all the difference. Tom points to his own parents, now in their 70s, who wouldn’t want to navigate an AI agent when a person feels more natural. For him, offering options—whether it’s instant automation or waiting a few minutes to talk to a human—is part of staying transparent and meeting customers where they are.

Transparency is also why Tom insists on “white box” AI systems instead of “black box” ones. If an AI makes a decision, his team can see why it happened, step in to coach or adjust when needed, and build trust by showing customers how the process works. That way, AI is a partner to humans (and not a mysterious machine making calls in the background).

How to embed AI into CX the right way:

• Give customers a choice: Start every interaction by asking, “AI now or wait for a human?” so people can decide how they want to be served.
• Make AI transparent: Use “white box” systems that explain decisions, and give teams the tools to override or coach the AI when needed.
• Ensure smooth handoffs: Design flows where AI can seamlessly pass context to humans—or even to another AI—so customers never feel like they’re starting over.
• Protect privacy and data: Collect only what’s necessary, anonymize wherever possible, and make data policies clear so customers know their trust is valued as much as their time.

For Tom, AI gives companies a way to deliver faster, more personal experiences, but it also raises the bar: Leaders have to be transparent, offer real choices, and protect customer trust at every turn. That same mindset—balancing risk with responsibility—shapes how Tom thinks about innovation.

Disrupt yourself (or be disrupted)

TL;DR: Disruption is about reinventing business models, taking intelligent risks, and moving faster than the competition. Reinvention is survival.

Known for intelligent risk taking, Tom began his career in tech with a leap of faith. Fresh out of law school, and with thousands in student loans to show for it, he realized he loved the study of law but couldn’t imagine practicing it for the next 25 years. 

So when a friend suggested moving to Silicon Valley in the late ’90s, Tom packed up, took an entry-level role, and bet on reinvention. That leap of faith—walking away from the safe path he had invested so heavily in—is how he’s approached his career ever since: By disrupting himself first.

And he believes companies need to do the same.

“If we don’t innovate and disrupt ourselves, we are absolutely going to be disrupted.”

For Tom, disruption is about accountability. If you don’t disrupt, you’re letting down employees, customers, and shareholders alike. What defines his approach is the ability to see through the customer’s eyes and shape innovation around their experience. 

That perspective drove Zendesk’s move to outcomes-based pricing: “We only get paid if our AI agent can solve your problem.” Tom frames this shift as a “two-way door” decision—reversible and worth moving fast on. For one-way doors—irreversible bets—you take your time, ensuring privacy and security are never compromised. 

The right way to disrupt:

• Move fast where you can: Treat reversible decisions as “two-way doors.” Test, learn, and iterate quickly in the market.
• Be deliberate where you must: For “one-way doors,” take the time to get it right. Privacy, security, and trust are non-negotiable.
• Innovate through the customer’s eyes: Build and test new models by imagining how they’ll feel on the other end of the experience.

Disruption may keep a company alive, but authenticity and learning keep it grounded. For Tom, moving fast and taking risks only work if leaders are honest about the journey, listen hard to their teams and customers, and keep adjusting as the world shifts around them.

Authenticity and always learning

TL;DR: Be direct, listen hard, and keep adjusting without losing sight of your North Star.

For Tom, adaptability doesn’t happen by accident—it’s the product of continuous learning. In a world moving at the speed of AI, with entire industries shifting week to week, standing still isn’t an option. “I spend hours every week getting educated by the team on what’s going on… really, every week, it’s like, these are the five or ten things that changed last week. How does it impact us? How are we thinking about it?”

That rhythm of constant learning is what allows him to adapt. At Zendesk, even carefully planned strategic sessions have seen 90% of their agendas thrown out in just three months, because the ground shifted so quickly. For Tom, that’s not failure—it’s the new reality. Leaders have to be comfortable making fast adjustments, sitting with uncertainty, and still moving forward with conviction.

But adaptability alone isn’t enough. In times of rapid change, authenticity becomes the anchor. 

“Be as authentic as possible. Whether you have good news or bad news, try to be as direct as possible with customers, employees, and shareholders on what’s going on.”

Tom believes leaders owe it to their customers, employees, and shareholders to be direct—whether the news is good or bad. Glossing over hard truths only erodes trust. Credibility doesn’t come from polished statements; it comes from clarity, courage, and the willingness to say, here’s where we are, here’s what’s changing, and here’s what we’re doing next.

How to lead with authenticity in times of change:

• Stop sugarcoating: Share the reality—good or bad—even when it’s uncomfortable.
• Listen first, act with conviction: Learn widely from your teams and customers, then make decisive choices.
• Model adaptability: Keep the North Star clear, but be ready to adjust the path as things change.
• Never stop learning: Treat every week as a chance to get smarter—because in an AI-driven world, yesterday’s knowledge won’t carry you tomorrow.

For Tom, when you put those pieces together—listening deeply, learning constantly, adjusting quickly, and leading with authenticity—you create an organization that can handle whatever the future throws at it.

From a small town grocery store of the past to the big tech of the future, Tom’s journey shows that customer obsession, smart disruption, and authentic leadership are what it takes to navigate transformation in the age of AI. How are you bringing together AI, innovation, and humanity in your own leadership?

Want more? Check out the full episode to hear Tom’s vision for the future of customer experience—and how to balance AI innovation with the human touch.

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