Former Chipotle CEO Brian Niccol’s move to Starbucks put Chipotle’s CFO succession plan through the blender in 2024.

Two years later, multiple reports that the coffee giant explored buying the burrito chain suggest that if a deal were to happen, Chipotle’s finance team could find itself back under a familiar boss.

Starbucks had worked with advisors in recent months on a potential takeover, the Financial Times reported. Starbucks has since denied any intentions of a purchase and Chipotle has chosen to not comment entirely, but the prospect gives Chipotle’s finance leadership history fresh relevance.

A Retirement on the Back Burner

The backstory is a succession plan that didn’t exactly work out as intended. Niccol left shortly after Chipotle announced how it would replace Jack Hartung, the only CFO it had ever had, forcing an earlier handoff to his successors while the 22-year veteran postponed retirement to help manage the transition.

Hartung was supposed to retire in March 2025, with then-Vice President of Finance Adam Rymer stepping into the role. Meanwhile, Jamie McConnell, who was vice president and controller at the time, would also take on some of Hartung’s responsibilities and become the company’s first chief accounting and administrative officer.

But just over a month after Hartung’s succession plan was publicized in 2024, Starbucks announced Niccol would become chairman and CEO in September of that year. Suddenly, Chipotle, a company whose leadership team’s strength was longevity, was managing an unexpected CEO departure while preparing to replace its finance chief for the first time.

• As a result, Hartung postponed retirement and agreed to stay on in broader roles, including president and chief strategy officer.
• Meanwhile, Rymer’s and McConnell’s start dates were pushed up.

The shake-up and subsequent promotions also prompted Chipotle to develop succession plans for all its executives. Having a CFO successor ready helped, but the company still had to redraw its leadership arrangements before the scheduled transition began.

Eventually, Hartung was able to step down from his multiple roles and remained as a senior advisor until retiring this March, nearly a year after his original target date.

A Second Helping of CFO Moves

At Starbucks, CFO Rachel Ruggeri served as interim CEO before Niccol arrived. In March 2025, the company announced Cathy Smith would leave Nordstrom to replace her as CFO during its “Back to Starbucks” campaign. Ruggeri’s departure came about six months after Niccol took over, adding the CFO seat to one of the many leadership changes made during his turnaround effort.

Greener Opportunities: Chipotle’s rebuilt leadership team, which included Scott Boatwright’s promotion to permanent CEO on Nov. 11, 2024, changed again the following September. Salad chain Sweetgreen announced it had hired McConnell, a seven-year veteran of Chipotle, as CFO on Sept. 4, 2025, with her tenure beginning Sept. 22, less than a year after her accelerated promotion.

Welcome to the fact-checking and editing world, CFOs.

A September report from FP&A technology provider Datarails, based on a survey conducted by Global Surveyz Research, found that 96% of the 270 CFOs and other finance leaders spend at least 10% of their workday verifying or correcting finance AI outputs.

For roughly a third of CFOs, that work can consume up to half of the day. Sounds fun, right?

Conducted in July, the report covered finance leaders at companies with at least 1,000 employees and $100 million in annual revenue. The findings also raise questions about how much AI is actually improving productivity.

Their responses suggest that the pressure to move faster with AI comes with new responsibilities and not exactly the payoffs some CFOs are looking for.

Whack-a-Mole

The pressure to implement AI, whether it’s from the board, CEO or an overworked finance team, is on. The survey found 76% of respondents faced high or very high pressure to fully implement AI in finance.

Feeling behind? Don’t worry:

• Only 7% of CFOs said their finance function was fully ready across all workflows from a data and infrastructure standpoint.
• Among finance leaders whose data was spread across disconnected systems, 76% reported spending more than a quarter of their time on AI verification.
• But regardless of the process in which AI is verified, there’s still this finding: 56% said team members had received materially different outputs from the same prompt and data.

“AI was supposed to take the manual work off finance teams. For most of them, it’s added a second job on top: checking the AI,” Jonathan Marciano, vice president of brand and communications at Datarails, told CFO Upside. In finance, he added, “a confident wrong answer is worse than no answer.”

Auditability, unsurprisingly, was the most frequently cited barrier to trusting AI with mission-critical tasks, identified by 75% of respondents. Accuracy and hallucination concerns followed at 71%.

More Work, More Spend

As pressure and workloads grow around AI, so does the desire to increase the amount of capital allocated to these tools. More than half of respondents said they plan to expand AI licenses over the following year, and roughly another third said their organizations “blew through” AI budgets by at least 10% over the previous 12 months.

The appetite for wider access remains substantial, but prepare to keep shelling out cash: The report says finance and accounting software spend in 2025 averaged $361,000.

Bring This to the Board. Here’s a useful question for the next meeting when your board or fellow executives are asking you about progressing automation and AI in your finance function at a pace you’re not so comfortable with: How many employees and how much time will an AI-generated answer require before it becomes usable?

As founder, CEO and CFO of Campfire, a cloud-based ERP platform, John Glasgow is watching his calendar stretch across time zones. With offices in San Francisco, New York and London, he’s managing expansion while keeping family time on the schedule.

“My week runs on ruthless prioritization,” Glasgow told CFO Upside. “Two things get my time: Campfire and my family.” He’s in the San Francisco office five days a week and tries to make it home for his kids’ bedtime, often taking calls on the commute. His family recently joined him in London and Amsterdam, where he squeezed in work around nap time and on flights.

Glasgow admitted that he is picky about invitations. “Since founding the company, I only attend events that I’m speaking at or a very high-quality founder event,” he said. An AI offsite featuring the founders of OpenAI and Anthropic recently made the cut.

The Boss’ Backup

Big company decisions get a review at home via Glasgow’s wife, who has had a successful tech career and is “my most trusted person in the world,” he said. “She brings a different perspective, so she always thinks of things that I didn’t.”

His identical twin brother, Ryan Glasgow, founder and CEO of Sprig, an AI-powered survey and customer research platform, provides another sounding board.

Inside Campfire, Glasgow is figuring out how much work he can hand off. “I’m in every Slack channel with every customer, not because I respond to everyone, but I want to know about the good and the bad,” he said. Agents help digest those conversations, and Campfire’s finance leader, previously a customer, takes some customer calls.

Still wearing the CFO and CEO hats, Glasgow knows his own availability has limits. “I am very aware that a CEO answering calls doesn’t scale,” he said.

CEO Ambition Versus CFO Caution

Campfire raised a $65 million Series B co-led by Accel and Ribbit in October 2025, just 12 weeks after its $35 million Series A. That gives Glasgow more capital to work with, but also comes with competing ideas about where it should go.

Some of those decisions come down to office rent, as Glasgow said additional locations like their new London and New York offices help recruit accountants who won’t relocate to San Francisco. The space also puts engineers near the employees fielding customer problems.

His biggest bet for 2027, he said, is accelerating investment in Ember, Campfire’s AI product. But his CFO instincts spur questions.

“The CFO in me wants to pull back and lean on third-party AI like Claude,” he said. “The CEO in me thinks there’s an opportunity to fundamentally rethink corporate finance, and owning the AI agents and model is the only way to deliver on this vision.”

Delegating to AI means deciding what deserves a human’s attention, and in the product, Campfire customers set those limits themselves. “If it can’t be explained, a person reviews it before it posts,” Glasgow said.

Allocating Calendar Capital. Glasgow applies a similar filter to requests for his own time. His advice to finance leaders: “Pick your two things to say no to now because the calendar will pick for you otherwise.”