Episode Overview

Podcast: Second in Command: The Chief Behind the Chief with Cameron Herold
Episode: Ep. 529 - FAN FAVORITE | Tom Keiser – The Powerful Execution Rhythm That Transformed Zendesk
Date: November 20, 2025
Guest: Tom Keiser, Chief Operating Officer, Zendesk

This episode features Tom Keiser, the COO of Zendesk, sharing operational wisdom from his time transforming Zendesk’s business rhythms and culture. Having come from a background bridging IT and operations across retail and technology, Keiser discusses strategies for scaling companies, aligning business priorities, maintaining agility, building a strong culture, leveraging data, and driving world-class customer engagement. The conversation explores how Zendesk sustains rapid growth without losing its startup edge, and how COOs must balance detailed execution with innovative leadership in a competitive, tech-driven landscape.

Key Discussion Points & Insights

Tom Keiser’s Career Foundation & Transition to Operations

• From Consultancy to Leadership in Tech:
  • Tom started as a systems and COBOL programmer before moving into management consulting. This gave him a foundation for solving business problems with technology, eventually leading to CIO and COO roles.

    "I grew up in management consulting... The CIO role is a great role if you're interested in operations and making things work better, because you touch every part of a business." – Tom Keiser (03:11)

• Blending Tech & Business:
  • Roles in retail and tech taught Tom the value of being a business partner, not just a technologist.

Zendesk’s Growth & Scalability

• Zendesk at a Glance:
  • A cloud-based, SaaS customer experience platform with over 130,000 customers in 160+ countries, rapidly scaling towards multi-billion dollar revenue. (05:28)
• Operational Priorities for Scaling:
  • Tom’s focus was to move Zendesk from a scrappy, process-light environment to one where scalable systems and clear priorities drove growth and efficiencies.

    "We needed a more robust set of analytics for business decision making... building up a data and analytics team that was taking advantage of all of this data." – Tom Keiser (09:01)

Execution & Prioritization Rhythms

• Six-Month Goal Setting and Weekly Cadence:

  • Top-down six-month prioritization, with quarterly and departmental “Top 5” priorities.

    "We're on a six month goal setting which is really prioritization at the top of the company that flows all the way through. And then we're on quarterly prioritization and really a top five prioritization across every function." – (11:03)

• Weekly Operational Reviews:

  • Monday: executive team reviews key health measures and scorecards.
  • Tuesday: C-staff meeting synthesizes key messages and determines action steps.

    "[On Mondays] we look at really every health measure in the business... On Tuesday morning we have our C staff, our executive team meets and we bring into that meeting really the key messages that came out of the weekly operational." – (12:12)

• Metrics-Driven Agility:

  • Health measures cover marketing pipeline, sales progress, product reliability, and recruiting; the intent is rapid detection and correction of issues.

    "We can react relatively quickly and turn things from red back to yellow and then to green by taking action based off what we see happening." – (14:06)

Balancing Growth with Entrepreneurial Culture

• Remedying Bureaucracy & Staying Scrappy:

  • Even as the company scales, maintaining agility and flexibility in processes is a priority to avoid “boat anchor” bureaucracies.

    "We're trying to build and measure speed in there." – Tom Keiser (15:37)

  • Leadership development at Zendesk emphasizes "agility" as a core competency at all levels.

• Cultural Roots:

  • The original Danish founders set values for design, culture, and humility (“humbled” = confident but humble employees).

    "People know that Zendesk is a special place. We've got the secret sauce of a great product, a great design aesthetic, but we've also got the secret sauce of great people and a great culture that cares." – (17:58)

Employee Engagement & Leadership Development

• Consistent Prioritizations Reduce Disappointment:

  • Transparent frameworks make it easier to say no while keeping spirits high despite fast pace and limited resources.

    "Having prioritization frameworks that everyone agrees to... is consistently practiced helps with that." – (19:41)

• Leadership Growth:

  • Emphasized the need to develop “whole leaders” and a leadership pipeline, hiring a Chief People Officer to instill a competency-based model.

    "We're working our way into a competency model and a leadership development model that we're rolling out across our leaders." – (43:14)

Customer Experience at the Center

• Building a Customer Advocacy Organization:
  • 300-person team leverages Zendesk’s own products to serve global customers.
• Listening & Acting on Customer Data:
  • Tom sees omnichannel, proactive engagement, and predictive support as essential for world-class CX.

    "Get ahead of your customer and answer their questions before they have to contact you." – (24:15)

  • Technology (AI, ML) is deployed to empower self-service and automate routine support, reserving humans for complex needs.

    "Machine learning is a real thing now... and thousands and thousands of companies are using it." – (26:59)

Navigating Rapid Change and Tech Disruption

• Cloud, Open Source, and Constant Change:
  • Organizational tech stacks are always evolving, and companies must stay vigilant to rapid competition and new tech (e.g., 5G, privacy regulations).

    "Every iteration, every time you go to an AWS event and you see all of the new tools... you see how fast competitors can enter into a space." – (39:59)

• Balanced Aggressive and Conservative Planning:
  • Growth plans are tempered with contingency plans for economic and regulatory volatility.

Vulnerability and Personal Growth as a COO

• Adapting to New Challenges:

  • Tom joined Zendesk at 50 with extensive experience, but faced a steep learning curve moving into SaaS.

    "I had to go through a fairly long and detailed learning of product, of technology... full of embarrassing moments and missteps." – (34:10)

• Balancing Vulnerability & Confidence:

  • Importance of being open and vulnerable as a leader, but proving value through results and support over time.

    "You prove your worth over time, especially as a leader by being there with the team, by making decisions... and building trust." – (35:41)

• Scaling Yourself as a Leader:

  • Letting go of details, focusing on cadence (especially weekly operations), and trusting the team while staying available for escalation.

    "I've had to learn to scale and scale myself really out of a lot of the details that make me more comfortable... then drop in at the right times." – (36:40)

The Founder–COO Partnership

• Delegating from the Founder:
  • Zendesk’s founder gradually turned over core functions to Tom; critical for scaling.

    "He was turning loose of the sales organization... and allowing us to consolidate those and really build out a go to market function." – (38:31)

Notable Quotes & Memorable Moments

• On Bridging IT and Business:

  "The CIO role is a great role if you're interested in operations and making things work better, because you touch every part of a business." – Tom Keiser (03:11)

• On Customer Experience:

  "Get ahead of your customer and answer their questions before they have to contact you. And make the experience when they contact you super easy." – Tom Keiser (24:15)

• On Organizational Agility:

  "We're trying to build and measure speed in there. We haven't quite figured that out yet, but I bust that story out regularly as we're building things to make sure that that's front and center." – Tom Keiser (15:37)

• On Personal Growth:

  "I was 50 years old when I joined Zendesk... being completely vulnerable and stepping into something uncomfortable and challenging yourself is, it's rejuvenating." – Tom Keiser (34:10)

• Advice to 21-year-old Self:

  "It's all going to be okay... there's a lot of wasted cycles. But I think my mindset was to get as much experience and as broad a range of experience as possible." – Tom Keiser (44:33)

Timestamps of Key Segments

| Timestamp | Segment Description | |------------|------------------------------------------------------------------------| | 01:11 | Tom Keiser’s introduction & career trajectory | | 05:28 | What Zendesk does and its explosive SaaS growth | | 09:01 | Bringing scalable processes and data-centric decision making to Zendesk | | 11:03 | Establishing prioritization: six-month and quarterly cycles | | 12:12 | Weekly cadence & health metrics review | | 14:06 | Turning metrics into actionable company change | | 15:37 | Maintaining agility and “scrappiness” | | 17:58 | Building and sustaining company culture | | 19:41 | Saying no without destroying morale; using frameworks | | 22:23 | Customer advocacy, success, and continuous CX reinvention | | 24:15 | Practical tips for proactive customer engagement | | 26:59 | Role of machine learning and AI in the customer experience | | 29:29 | Day-to-day COO responsibilities & communication cadence | | 34:10 | Vulnerability and adapting to tech sector leadership | | 43:14 | Leadership development and competency building | | 44:33 | Advice to a younger self |

Final Takeaways

This episode distills Zendesk’s operational success into clear rhythms—goal-setting, communication, transparency, and agility—all anchored by a culture of humility and customer focus. Tom Keiser’s journey demonstrates that modern COOs must synchronize people, process, and technology, and lead with both humility and decisiveness in the face of constant change.

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