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349: In this interview, Peter High speaks with Tom Keiser, the Chief Operating Officer at Zendesk. Among the topics they discuss include: An overview of Zendesk’s business and the growth the company has experienced going from a startup to a $500 million public company in eleven years Tom’s responsibilities as COO which include IT responsibilities such as business analytics and security, as well as operational responsibilities such as go-to-market and customer-facing functions Tom’s perspective on the ever changing customer service world and how the company has been able to evolve by focusing on having an agile foundation while making sure the right technologies are in place. The difference in how CIO’s of traditional companies with monolithic systems and modern companies with cloud-based technology are trying to incorporate new technology to keep up with the competition. An overview of Tom’s adjustment from a retail company to Zendesk, as well as Tom’s perspective on how the CIO role has been reinvigorated over the past year going from back-office focused to customer-focused How reporting directly to the CEO has benefited Toms career by allowing him increased access conversations around value from the standpoint of operational improvement, and Tom’s advice for how CIOs can take on additional (CIO Plus) responsibilities, including leveraging the unique position of IT within the organization Tom’s advice to older companies looking to leverage modern technology, which includes trialing new software to see what works best for the company. Eye on the Trends: AI and machine learning