Ep. 529 - FAN FAVORITE | Tom Keiser – The Powerful Execution Rhythm That Transformed Zendesk

Second in Command: The Chief Behind the Chief with Cameron Herold

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.

🔗 LinkedIn

Resources & Mentions

• Capgemini / Ernst & Young
• Zendesk

Important Links

• Connect with Cameron: Website | LinkedIn
• Explore the COO Alliance - The World’s Leading Community for Seconds in Command
• Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
• Take Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
• Chat or video call with AI Cameron via Delphi

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.