Second in Command: The Chief Behind the Chief with Cameron Herold Ep. 529 - FAN FAVORITE | Zendesk COO Tom Keiser Shares The Powerful Execution Rhythm That Transformed Zendesk
We’re bringing this episode back because listeners couldn’t get enough the first time around. Cameron sits down with Tom Keiser, COO of Zendesk, to unpack how he helped scale the SaaS powerhouse to a billion-dollar trajectory.
Tom shares how he bridged the gap between IT and operations, built cadence-driven execution rhythms, and created visibility across the business while keeping the culture humble, fast, and customer-obsessed.
If you’re leading a growing company and need a blueprint for scaling without suffocating the entrepreneurial edge… this one hits hard.
Timestamped Highlights
01:11 Meet Tom Keiser and his path from CIO to COO
02:00 Early days: Capgemini, E&Y, and stepping into tech leadership
05:27 What Zendesk actually does (and how it scaled globally)
07:33 How SaaS changed the business–IT power dynamic
08:55 Why CIOs must become business partners, not tech overseers
10:54 The PMO strategy that keeps Zendesk aligned as it scales
12:04 Tom’s weekly operational cadence pulled from retail
13:50 Turning insights into action: Sales, pipeline, and global adjustments
15:37 How Zendesk avoids bureaucracy while growing fast
17:39 Culture: The Danish “Humbled It” mindset
19:36 Saying no without killing momentum
20:57 Managing customer support when your whole business is CX
23:38 Omnichannel done right: Continuous conversations, not disconnected pings
26:14 Machine learning inside Zendesk Guide
29:18 How Tom balances immediate execution with long-term scaling
32:55 What smaller companies can learn from Zendesk’s growth
34:34 Vulnerability and learning to step into discomfort as a leader
36:25 When to trust your team and when to drop into details
37:51 How Zendesk’s founder transitioned out of day-to-day execution
39:18 Market risks, public cloud, open-source, and economic uncertainty
39:46 What 5G will unleash for future customer experiences
43:12 Building whole leaders, not siloed operators
44:13 Tom’s advice to his 21-year-old self
About the Guest
Tom Keiser is the Chief Operating Officer of Zendesk, where he oversees global operations, IT, enterprise analytics, security, and go-to-market execution for one of the world’s leading customer experience platforms. With 25+ years of experience across retail, technology, and SaaS, Tom blends deep technical expertise with business-led operational leadership. Before Zendesk, he served as CIO at L Brands and spent years in management consulting at Capgemini and Ernst & Young.
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Note: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.
The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.