CEO of $1.3 billion learning platform reveals lessons from 23 years under Jeff Bezos and Andy Jassy

In 1997, on the Sunday before Greg Hart began his tenure, he was called to a meeting with the company’s founder, Jeff Bezos.

Back then, Bezos had personally interviewed nearly all of Amazon’s approximately 200 staff; Hart was among the rare few the entrepreneur had not hired directly. During his subsequent 23-year career at the e-commerce behemoth, Hart served as a technical advisor to the CEO, reporting straight to Bezos and later to Amazon’s current chief executive, Andy Jassy.

The insights Hart gained at one of the globe’s most renowned companies remain with him today as he heads the $1.35 billion online learning platform, Coursera. He took on the mission of guiding the company through a strategic shift—a move that proved timely as demand surged, with both job seekers and workers eager to include crucial AI credentials on their resumes.

Many of the initiatives Hart implemented at Coursera—impacting its over 1,000 staff—will resonate with former Amazon employees. Hart noted that Bezos’s early habit of interviewing every hire established a cultural foundation as Amazon expanded. “He wanted to ensure the passion, customer obsession, high standards, and bias for action present in the initial employees remained core as the company scaled,” Hart explained.

Therefore, it was “perfect sense” when Bezos authored his now-iconic shareholder letter detailing the company’s leadership principles and goals, as they “mirrored” the everyday discussions happening within the organization.

Hart aimed to instill a comparable philosophy at Coursera. “I wanted to fundamentally transform the company, accelerate its pace, and improve how we serve our learners. I believed a key element in achieving this was ensuring strong cultural cohesion, so we introduced a set of leadership mindsets. We examined the values or principles of some of the world’s most successful companies… and crafted our own, tailored specifically to our business and our company’s history,” he stated.

This emphasis on speed became vital when the AI boom rapidly changed the skills businesses sought, forcing employees and job hunters to scramble to adapt. The platform now hosts more than 12,000 courses, including 1,100 focused on generative AI—a 44% rise from the previous year. Generative AI is decisively the most sought-after subject on the platform, popular with both individual learners and employees accessing it through employer-paid subscriptions.

Hart also sought to replace vague company-wide meetings, reviving an Amazon strategy by centering each all-hands gathering on one specific leadership principle. “One thing I’ve learned from leading various businesses in different industries is that no matter how clear an idea is to you or your leadership team, you can never communicate it too often to the broader organization. People might not be listening, they may not grasp it, they could have been in a client meeting, or they simply missed it,” he said.

“Each month, one of my direct reports distributes an email with a video highlighting just one of our leadership mindsets. We do the same at every all-hands meeting. We select one mindset and provide concrete examples, because it makes the concept tangible and gives people clearer context,” Hart added.

How Hart uses AI at work

A primary concern for every CEO today is how to utilize AI, both within their operations and for personal productivity. A recent survey found 74% of executives ranked AI investment as a top priority despite economic concerns, and 79% believed they were leading in its adoption and use.

Previous reports have indicated that business leaders are applying AI to a wide range of functions, from hiring to management.

Hart, who studied English, understands the productivity gains AI can provide but stated he never employs the technology for writing. “For me, writing is how I process thoughts, so outsourcing it would essentially mean outsourcing thinking,” Hart remarked. “That is neither appealing nor effective for me personally.”

Coursera encourages all employees to explore AI applications as they choose, currently without specific targets for what they should accomplish. The most valuable result of this open approach, Hart notes, is that team members exchange their use cases and effective methods on an internal channel named ‘AI Sparks.’

“AI Sparks is a monthly gathering where people from all levels and departments come to share how they’re using AI in their roles. These are, by a wide margin, the best-attended and most popular meetings we hold at the company,” Hart said.

A final takeaway from Amazon equipped Hart for the AI age: becoming overly fixated on immediate outcomes when a new technology emerges can obscure the larger opportunity.

“My view is we simply want a workforce that is using AI as extensively and in as many contexts as possible. Later, we’ll become more focused on measuring the impact,” Hart explained. “If we narrow our focus to just metrics now, I believe we would miss the chance to create a much more significant effect in the future.”