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Amazon CEO Andy Jassy has a new 'shadow' advisor. It's one of the most prized roles inside the company.

Amazon CEO Andy Jassy
Amazon CEO Andy Jassy. Amazon
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Amazon CEO Andy Jassy has a new "shadow" advisor, according to an internal organizational chart obtained by Business Insider.

This role is a quasi chief of staff position at Amazon. Formally called "technical advisor," it's one of the most desirable jobs at the company because this person joins the CEO in almost every meeting and call. It typically lasts about 18 to 24 months.

Shadow advisors often go on to hold top positions at Amazon once their tenure ends. Jassy, for example, was Jeff Bezos' shadow advisor early in his career. Others include Amit Agarwal, Amazon's India chief, and Jay Marine, who leads Prime Video's sports streaming business.

Jeff Bezos.
Jeff Bezos.  AP Photo/John Loche

This time, Alex Dunlap has taken on this prized role, the org chart shows.

Dunlap is a 17-year veteran of Amazon Web Services who most recently served as vice president of productivity apps. He started as Jassy's shadow advisor in late 2024, replacing Eric Rimling, a logistics VP who was Jassy's shadow since January 2023.

Dunlap's appointment coincides with Amazon's renewed focus on business applications, also known as software as a service. AWS has market-leading cloud infrastructure services, like computing and storage, but has not yet built an equally strong presence in the lucrative SaaS market.

Last year, Amazon moved Colleen Aubrey, a longtime advertising executive, to oversee its business applications group. Dilip Kumar, another high-profile executive who launched Amazon Go stores, is now in charge of Amazon Q, an AI application for developers and other business customers.

AWS has built many business applications throughout the years with mixed results. Bedrock, an AI development tool, and Connect, a call center application, have shown early success. Meanwhile, the file-storage app WorkDocs failed to gain much traction, and the app-building software service Honeycode was shut down.

An Amazon spokesperson declined to comment on Dunlap's appointment. The spokesperson added that AWS has been successful outside of core infrastructure services, mentioning a list of its applications, including Q, Connect, Bedrock, and SageMaker.

"We are the top leader, or leader of leaders, on all calibrations of measurement in hundreds of third-party evaluations," the spokesperson said.

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Eugene Kim
Eugene is Business Insider’s Chief Tech Correspondent, where he leads coverage of Amazon. His reporting spans the company’s retail and logistics operations to AWS, Alexa, and its internal culture.Previously, he worked at CNBC, Fortune Magazine Korea, and Japan's Yomiuri Shimbun. He holds degrees from NYU and Columbia University’s Graduate School of Journalism.In 2022, Eugene reported on internal documents indicating that Amazon allegedly used deceptive tactics to enroll customers in Prime and made cancellation difficult. The Federal Trade Commission sued Amazon the following year, citing his reporting. The case ended in a record $2.5 billion settlement in 2025.His work has received multiple honors, including the SF Press Club’s Bay Area Journalism Award and SPJ NorCal’s Excellence in Journalism Award.Eugene lives in the Bay Area. Contact him via email at ekim@bjinnox.com, or Signal, Telegram, or WhatsApp at 650-942-3061. Use a personal email address, a nonwork WiFi network, and a nonwork device; here's our guide to sharing information securely.