Zendesk’s COO Has a Unique Strategy For Encouraging Collaboration

Mar 26, 2020 | 0 comments

You might think an executive with an IT background could easily drop into any company to serve its information technology needs. But spend a few moments with Tom Keiser, COO of cloud-based help desk company Zendesk, and you’ll discover it takes more than simply arriving at a company to know the best approach to its unique circumstances.

Tom’s 25-year business background is in the chief information officer role. He served as CIO at L Brands (parent of Victoria’s Secret and Bath & Body Works, among others) and Gap Inc., before joining Zendesk in 2016. He transitioned from CIO to COO in 2017, but shared in a conversation for the Second in Command podcast how his technology experience continues to play a role in how he makes business decisions.

“CEOs want a technology partner that is a business partner who can help them navigate the complexity, but not have to get into the complexity,” Tom says. Many CIOs, he says, are working to break down the stereotypical setups that often silo the information technology departments from the rest of the company.

Here are some of the key points he shared about how he approaches the COO role at Zendesk.

Set goals, but focus on agility

As the walls between IT and other departments start to come down, Tom emphasizes the importance of prioritization throughout the company. “We’re making sure we’re working on the right things and that we’ve got good open channels of communication between the business and IT departments,” he says.

To do so, Zendesk sets goals on six-month cycles, from the top executives throughout the company. But that’s not all — there are also quarterly priorities, along with a set of top-five priorities for every role in the company. Layering priorities by time and function forces management to ensure each one fits into the goals that have been set for the coming months.

But Zendesk’s schedule of goals and priorities doesn’t mean the company is rigid in how it plans for growth. “One of the things I’ve focused on is agility from the standpoint of making sure we think about our processes that we’re putting in place for scale, so we’re building them in a way that we can still have the flexibility to adjust to our business model,” Tom says.

While previously in his career, the processes implemented might be more ornate and structured, today, there’s a greater need for flexibility, Tom explains. The ability to adjust “means we may not be able to build the most perfectly efficient set of processes,” Tom says, “but we’re trying to build and measure speed in there.”

Flexibility may be a moving target, but Zendesk ensures agility is a core competency at every level of its leadership to keep a focus on the next best process.

Practicing humblident 

Tom credits Zendesk’s culture to a word created by the company’s Danish founders, humblident (confident and humble smashed together). “We are very competent and confident but humble employees,” Tom explains. Not only does this core value serve as a filter in the hiring process, but employees continue to maintain the same mindset as the company grows.

It’s easy to see Tom has embraced that humbleness. When he joined Zendesk as CIO, he had never worked for a software company. “I had to go through fairly long and detailed learning of product, technology, mindset — full of embarrassing moments and missteps along the way,” he admits. And although he joined Zendesk later in his career, Tom says embracing those areas of discomfort and being confident of his past experiences in his new challenges was rejuvenating.

One of his challenges has been learning to scale himself out of some of the hands-on details he used to make him comfortable and confident the right things were happening. When he transitioned from CIO to COO, he served in both roles for a while. But now, he’s a bit more removed from his focus on the CIO side.

“As we grow this company toward a multibillion-dollar company, I get further away from the details,” he says. But he still communicates with customers on a regular basis to strategize around challenges that may arise. Just as Zendesk directs its clients to try to answer their customers’ questions before they ask them, Tom continues to find ways he can meet his own clients’ needs more easily.

How a check-in routine catches challenges early

Tom talked about the meeting schedules he picked up from his time in retail, which focus on weekly performance to adjust plans and goals. At Zendesk, he described a similar meeting schedule that includes a Monday operational meeting, a Tuesday meeting for the senior staff, and Wednesdays with go-to-market leadership meetings and COO team meetings.

The Monday operational meeting sets Tom up for success all week. “I try not to miss it. Even if I’m on a plane, I’m trying to listen in to stay connected to what’s going on,” he says. His cadence of checking in with various teams helps Tom make sure each one is working on the top priorities for both that very moment and also for meeting longer-term goals.

The routine of regular check-ins also helps Tom anticipate how he can aid his CEO. “I have a very demanding founder who is constantly not just asking questions about going on now, but asking questions about the future — about things that perhaps I have not thought of yet,” Tom says.

This article is based on an episode of Second in Command podcast, where your host Cameron Herold interviews the chief operating officer behind the chief executive officer to learn their tips, systems, and insights from being the second-in-command of an amazing growth company.

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Written By Cameron Herold

Written By Cameron Herold

Cameron Herold is known around the world as THE CEO WHISPERER. He is the mastermind behind hundreds of companies’ exponential growth. Cameron’s built a dynamic consultancy: his current clients include a “Big 4” wireless carrier and a monarchy. What do his clients say they like most about him? He isn’t a theory guy—they like that Cameron speaks only from experience. He earned his reputation as the CEO Whisperer by guiding his clients to double their profit and double their revenue in just three years or less. Cameron is a top-rated international speaker and has been paid to speak in 26 countries. He is also the top-rated lecturer at EO/MIT’s Entrepreneurial Masters Program and a powerful and effective speaker at Chief Executive Officer and Chief Operating Officer leadership events around the world.