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Passionate for Driving Innovation 

Day One Innovation's mission is to help leaders and companies thrive through the AI revolution, by making expert, clear, and practical guidance available to small and mid-size companies.

Our focus has always been helping leaders improve their innovation, and we believe generative AI makes this more critical than ever.  Leaders and companies that are behind in innovation, will be unable to keep up with those who outperform them and leverage generative AI to stay ahead.

Our company is made up of prior Amazon employees with deep business management, project management, and technical expertise. We intend to share our experiences and knowledge to help create new innovation across a variety of industries. We are passionate about change, digital transformation, innovation, and helping others to succeed.

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About Trent Gillespie

Founder and Chief Innovation Officer

Trent Gillespie started Day One Innovation in 2021 after retiring from Amazon. At Amazon, Trent worked in Senior Leadership for almost 9 years, where he led multiple business and technology teams to drive innovation globally. Trent held three roles over his Amazon career, working with all levels of Amazon management, most Amazon businesses, and every geography Amazon operated in. Trent gained significant experience with both Amazon practices and driving innovation at scale, which he is using to help clients through Day One Innovation. Before Amazon, Trent worked as the head of IT (CIO, IT Director) for various West Coast US firms. Trent holds an MBA and Certificate in Executive Leadership from Seattle University.

Key Amazon Projects and Initiatives

  • Global Point of Contact for all Business and Geographic Expansion for Amazon.

  • Identification, prioritization, and program management of hundreds of strategic innovation programs globally.

  • Owned restructure of the entire Amazon European Business (and Intellectual Property) for Finance Operations.

  • Owned the technology improvement roadmaps for Amazon Accounts Payable, Accounts Receivable, Payroll and Real Estate, spanning from fraud prevention to global expense management, managing hundreds of billions of dollars of transactions annually.

  • Managed the technology improvement roadmaps for Amazon Last Mile Technology, building the capabilities to support Amazon Logistics, Prime Now, Amazon Fresh, and other delivery initiatives globally.

  • Owned launch of delivery technology for Amazon Japan, and other emerging geographies.

  • Owned the Amazon Fresh delivery technology program, making Fresh profitable for the first time and enabling current business expansion.

  • Owned the Amazon Restaurants delivery technology program. 

  • Rebuilt the global Amazon Last Mile system infrastructure.

  • Managed product and technology improvements for many new business initiatives, from Amazon Flex to Amazon Web Services. 

  • Defined and owned the technology and organizational requirements for Alexa to be compliant with global privacy regulations such as GDPR, CCPA, and COPPA.

  • Owned child privacy globally for Amazon, enabling new products such as Alexa Glow and Amazon Kids.

  • Owned Privacy Risk Management for Alexa globally.

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