What is a Shadow Adviser and Why Does Andy Jassy Have One?

Confidential sounding board, trusted second brain, strategic influencer – the world of executive ‘shadow advisors’ is complex, uniquely positioned and, more often than not, a sure-fire ticket to a leadership position. 

And Andy Jassy should know. The Amazon CEO has himself shadowed none other than Jeff Bezos. 

In 2002, he was selected by the Amazon founder for the role – formally titled Technical Advisor (TA) to the CEO. During his roughly 18-month tenure, he accompanied Bezos to every meeting, including one-on-ones, acting as a “second brain” and intellectual sparring partner. 

The experience built the foundation for Andy’s career and journey to CEO at Amazon. It also standardised and popularised the role within the online retailer, turning the TA position into an effective golden-ticket to the top seat. 

Unsurprisingly, Andy has continued the tradition during his CEO tenure, which began in July 2021, promoting several senior execs to the coveted position. 

On 4 February, Amazon announced the latest shadow reshuffle, promoting VP of Worldwide Selling Partner Services (SPS) Dharmesh Mehta to the TA role effective March 2026. 

From ‘shadow’ to leader

Amazon says it uses the TA role for the CEO and other senior leaders across the company as part of its programme to develop future leaders. 

Alex Dunlap, Andy’s current TA will transition to a new leadership role within the company as part of the reshuffle. 

Dharmesh will replace him from March. A renowned Amazon heavyweight, he has been with the company for more than 12 years in Worldwide Stores leadership.

In the role he oversees the organisation responsible for driving innovation in technology, brands and customer service across Amazon’s physical and online retail marketplaces. 

He has spent the decade growing the SPS and Customer Trust teams, enabling tools and services for independent sellers and ensuring a trusted shopping experience on Amazon. 

Under his leadership, independent sellers have grown to account for more than 60% of units sold in Amazon’s store.

“I’m excited to take on a new opportunity at Amazon,” says Dharmesh, writing about his new appointment on LinkedIn. 

“Beginning in early March, I will transition into the role of Amazon CEO Andy Jassy’s Technical Advisor, or shadow, and shift leadership of the SPS organisation to my colleague Amit Agarwal, who will also continue to lead Amazon’s International Emerging Stores businesses.

“It has truly been a privilege to lead the talented SPS team and work so closely with our millions of selling partners around the world. I will remain an admirer of and advocate for this community, and I look forward to seeing all the amazing things that Amazon and our selling partners accomplish in the years to come by continuing to work together.”

The TA as a springboard

The TA role in Amazon has a history of being a platform to future leadership with the company. 

In the position, shadows typically spend up to two years as the CEO’s second brain, attending high-level meetings and negotiations, providing unfiltered truth telling and technical intuition, and helping the senior leader stress-test strategies before deployment. 

Prior to Dharmesh, Andy has appointed three high-level TAs. 

After completing her rotation with Andy between 2021 and 2023, Sara Duffer returned to a senior role within AWS. As of late 2025, she serves as Vice President at AWS, specifically leading the Platform Cryptography and Privacy Division. 

She has publicly credited the shadow program for giving her a broader business perspective that she now applies to Amazon’s security infrastructure.

Fourteen-year Amazon veteran Eric Rimling held the TA to Andy position between 2023 and 2024, while Alex Dunlop is confirmed to be moving into a new leadership role from March. 

This pattern is consistent with historical shadows who served under Jeff Bezos and are now some of the most powerful people at Amazon.

Amit Agarwal serves as a prime example of the shadow role’s global impact. 

After shadowing Bezos from 2007 to 2009, he was entrusted with launching Amazon’s marketplace in India in 2013, scaling it into one of the company's most critical international territories. 

As of early 2026, he remains a key member of the company’s senior leadership team, recently expanding his remit as Senior Vice President to oversee the massive Worldwide Selling Partner Services division alongside his leadership of emerging markets like Brazil and South Africa.