Why More Than 20 Employees Are Returning to Salesforce from OpenAI

Although for many, the tech market is largely an employer’s market, for the top talent – and AI talent especially – the demand for expertise is sky-high. Companies are poaching employees from their competitors left, right, and center, and employees themselves will go where the culture, progression, and money are. 

For OpenAI, this is beginning to feel like a notable trend. A second former Salesforce employee who went on to join OpenAI has now left to go back to Salesforce, and reports indicate that this will likely not be the last case. Let’s dive into the details. 

OpenAI’s Executive Churn and Attrition 

The tech market of today can be an uncomfortable place to find yourself working in. Tech layoffs have accelerated this year, entry-level roles are slowly being scrapped, and the ‘quits rate’ – an indicator of worker confidence – has dropped to 1.9%, indicating that tech employees are holding onto current roles due to market fear. 

For companies like Salesforce, exec shakeups have been headline news over the last six months. Whether this is down to conflicting leadership interests, opportunities, or compensation issues is less clear, but there has undoubtedly been a lot of movement at the top of the table. 

AI behemoth OpenAI has recently been scrutinized for its own exec shakeup, losing 14 executives just this year. This includes former operating chief Brad Lightcap and Chief Revenue Officer Denise Dresser.

Ditching Salesforce To Come Back To… Salesforce?

You may remember Dresser as the former CEO of Slack, but she is not the most interesting figure in this upheaval. That would instead be Peter Doolan, OpenAI’s Global Head of AI Transformation for GTM, and Kaylin Voss, OpenAI’s VP of Americas Sales, who both left Salesforce to pursue positions at OpenAI. They have now both transitioned back to work for the CRM giant. 

The Information, which originally covered this story, has reported that an additional 22 former Salesforce employees now at OpenAI are in active talks to return to Salesforce. 

This also comes amid several other concerning, high-profile departures from OpenAI, including Chloé Bakalar, Head of Ethics, Johannes Heidecke, Head of Safety Systems, and Joshua Achiam, Chief Futurist and former mission-alignment leader.

Problems at OpenAI

OpenAI’s loss of these particular positions signals a couple of things many people in the sector have suspected for quite some time: that the company’s mission direction is under heavy scrutiny and there is a problem within leadership. 

OpenAI is currently moving toward a for-profit structure and preparing for a planned 2027 initial public offering, which will be a high-pressure time for the company and investors. Not only that, but the direction that CEO Sam Altman is planning to take the company has also been an area of contention both within the company and outside of it, with some worried that ethics and AI safety take a backseat to profitability and rapid scaling. 

Salesforce’s Boomerang Phenomenon

It is also particularly interesting that this is a considerable part of the boomerang phenomenon that is currently being observed with Salesforce. 

Earlier this month, I covered this phenomenon in detail, as 1 in 18 people reportedly hired by Salesforce in 2025 had already worked at the company before. In fact, it’s become so prominent that it has become part of Salesforce’s marketing strategy around hiring and its hiring push for Forward Deployed Engineers (FDEs). 

I surmised then that for many of the boomerang employees, it seemed as if they knew the move to another company was always going to be temporary, at least judging by their LinkedIn statuses.

However, there is likely not one single reason as to why these employees come back, although the ones that do seem to hold Salesforce in high regard in terms of opportunities.