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Why the former CIO of Gap moved from clothes to cloud

Clint Boulton | May 13, 2016
After spending the past year investing in and advising a handful of retail and SaaS startups, Tom Keiser is again donning his CIO hat for Zendesk, a rising customer service software maker.

One Big Bang digital transformation was enough for Tom Keiser. After overhauling legacy IT systems and updating ecommerce platforms, the former Gap CIO has joined SaaS provider Zendesk as its first CIO. The move comes more than a year after leaving the apparel retailer. Now Keiser will build out IT, security and data analytics capabilities for a cloud service provider seeking to top $1 billion in revenues by 2020.

Zendesk founder and CEO Mikkel Svane told via email that he hired Keiser for the wealth of "enterprise technology and operations experience" he brings to a company that is entering its next stage of growth. Zendesk, which has expanded to more than 1,400 employees from fewer than 800 a year ago, sells customer service software for ecommerce call centers and help desk tools to support enterprises' trouble-shooting needs.

"The tool set is useful for CIOs because traditional big company CIOs are under tremendous pressure to go fast and have tremendous agility and flexibility in their solutions because consumers are flexing and moving really quickly," Keiser says.

Upgrading legacy technology ages you

Keiser knows something about moving fast. When he joined Gap in 2010, Keiser began hammering away at an aggressive IT strategy. He built a private cloud to replace legacy hardware and applications and added new networking infrastructure to improve data throughput. Such tools supported a growing ecommerce initiative that included support for new mobile and Web services for employees and consumers, including the capability for customers to buy online and pick up in store. Although it was personally and professionally rewarding, the three-year digital transformation left him drained.

"You probably lose five years of your life from every year that passes when you do that [going from legacy to digital systems]," Keiser tells "It's rewarding in the end but the journey there is very difficult."

In 2014 Keiser was promoted to executive vice president of global product operations, a role in which he used analytics software to better plan, buy, allocate, replenish and price products across all for each of Gap's brands. He left in March 2015 and has spent his time advising the likes of tech-focused apparel brands Michael Andrews Bespoke and ModCloth and investing in startups such as Software Anywhere and Groove Technologies. By the end of 2015, he was ready to begin the next leg of his IT career.

Keiser interviewed with CEOs of large traditional companies, all of whom discussed similar challenges, which he wanted no part of. "In big companies it takes a while to get around to newer technologies," Keiser says. "You're always three to five years beyond, you're more conservative and it takes longer to deploy things. I quickly concluded I didn't want to go back to a really big company." He also met with some pre-IPO startups and realized that they didn't offer the blend of business and technology opportunities he was seeking.


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