Amazon CEO Andy Jassy has appointed Alex Dunlap as his new shadow advisor, a prestigious role that serves as a quasi-chief of staff position at the tech giant. According to an internal organizational chart obtained by Business Insider, Dunlap assumed this coveted position in late 2024, replacing Eric Rimling who held the role since January 2023.
The shadow advisor or “technical advisor” role is one of Amazon’s most sought-after positions, as it provides unparalleled access to the CEO’s decision-making process. The person in this role joins the CEO in virtually every meeting and call, gaining comprehensive insight into Amazon’s strategic direction. The position typically lasts 18 to 24 months and has historically served as a launching pad for top executive positions within the company.
Notable alumni of this program include Andy Jassy himself, who served as Jeff Bezos’ shadow advisor early in his career before eventually becoming CEO of Amazon Web Services and later the entire company. Other successful graduates include Amit Agarwal, who now leads Amazon’s India operations, and Jay Marine, who heads Prime Video’s sports streaming business.
Dunlap brings 17 years of AWS experience to the role, most recently serving as vice president of productivity apps. His appointment comes at a strategic inflection point for Amazon, as the company intensifies its focus on business applications and software as a service (SaaS). While AWS dominates the cloud infrastructure market with its computing and storage services, it has struggled to establish an equally commanding presence in the lucrative SaaS sector.
Amazon has been making significant organizational moves to strengthen its business applications portfolio. Last year, the company appointed Colleen Aubrey, a veteran advertising executive, to oversee its business applications group. Additionally, Dilip Kumar, known for launching Amazon Go stores, now leads Amazon Q, an AI-powered application designed for developers and business customers.
AWS’s track record in business applications has been mixed. Success stories include Bedrock, an AI development tool, and Connect, a call center application that has gained early traction. However, the company has also experienced setbacks, with WorkDocs failing to attract significant users and Honeycode, an app-building service, being shut down entirely.
An Amazon spokesperson declined to comment specifically on Dunlap’s appointment but emphasized AWS’s success beyond core infrastructure services, citing Q, Connect, Bedrock, and SageMaker as examples of strong performance in the applications space.
Key Quotes
We are the top leader, or leader of leaders, on all calibrations of measurement in hundreds of third-party evaluations
An Amazon spokesperson made this statement when defending AWS’s performance beyond core infrastructure services, emphasizing the company’s success with AI and business applications like Amazon Q, Connect, Bedrock, and SageMaker.
Our Take
Dunlap’s appointment reveals Amazon’s acknowledgment that infrastructure dominance alone won’t win the AI era. The shadow advisor program has historically been Amazon’s executive incubator, and placing someone with productivity apps expertise in this role telegraphs where Jassy sees the company’s future. The mixed results of AWS’s business applications—from Bedrock’s success to Honeycode’s failure—underscore the challenge ahead. Amazon is playing catch-up in AI applications while Microsoft and Google leverage their existing SaaS customer bases. However, AWS’s massive infrastructure advantage and developer relationships provide a strong foundation. The real test will be whether Amazon can translate its cloud dominance into compelling AI-powered business tools that enterprises actually want to use. Dunlap’s tenure as shadow advisor will likely shape this critical transition, making his eventual next role a key indicator of Amazon’s AI application strategy success.
Why This Matters
Dunlap’s appointment as shadow advisor signals Amazon’s strategic pivot toward AI-powered business applications, a critical battleground in the evolving cloud computing landscape. While AWS has dominated infrastructure services, competitors like Microsoft and Google have gained ground in SaaS and AI applications, making this a crucial area for Amazon’s future growth.
The timing is particularly significant as enterprise AI adoption accelerates across industries. Amazon Q, Bedrock, and other AI tools represent the company’s attempt to capture this massive market opportunity. Having a shadow advisor with deep productivity apps experience suggests Jassy is prioritizing this transformation at the highest levels of leadership.
This move also highlights the intensifying competition in generative AI and business software. Microsoft’s integration of AI into Office 365, Google’s Workspace AI features, and Salesforce’s Einstein AI all pose competitive threats. Amazon’s organizational restructuring, including Kumar’s focus on Amazon Q and Aubrey’s leadership of business applications, demonstrates the company’s recognition that winning in AI requires more than just infrastructure—it demands compelling end-user applications that solve real business problems. The success or failure of this strategy could reshape the competitive dynamics of the entire cloud computing industry.
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Source: https://www.businessinsider.com/amazon-ceo-andy-jassy-shadow-advisor-alex-dunlap-2025-1