As Workloads Climb, Companies Build Clear Off-Ramps to Shift Employees Out of Intense Roles

Plenty of people willingly take on demanding stretches of work. The trouble starts when companies treat that choice like a lifelong vow. Today’s tech has only raised the tempo, creating cultures that mirror the speed of the products they ship. But without clear off-ramps that let people shift gears, even the most committed grinders eventually hit a wall that never needed to be there in the first place.

We sat down with Cara Whitehill, a Go-To-Market executive and Operating Partner at Thayer Investment Partners, who has built a career scaling both early-stage startups and larger organizations. A recognized thought leader and Co-Creator and Co-Host of the Travel Tech Insider podcast, she has seen the inner workings of corporate culture from her time at industry giants like Expedia and Travelocity. Whitehill suggests the debate around burnout often focuses on the symptoms—the long hours—instead of the root cause: a failure to plan for an employee’s entire career lifecycle.

“Some folks want to work that way for a time and then step back. They might say they have a year to devote to a 996 schedule, but after that, they want to get married, start a family, or move. Get the best of that person while they’re willing to sign up for it and then be mindful of how you transition out of that,” says Whitehill.

• Choose your own adventure: She encourages employers to be upfront not just about the intensity expected from employees, but the duration. “Structure the skillsets you need for a role, then be clear if that role will require very demanding work for a period of time because you need to hit a milestone, raise a round, or deliver something critical for a client,” Whitehill explains. “Everyone knows what they’re signing up for and for how long. And once that milestone is met, if someone needs to step back, they’ll need to move into a different role because the original one depends on that level of commitment.”

• Just what the doctor ordered: Whitehill goes on to explain that it isn’t a novel concept. “Look at how doctors train. They know they’re going to be working thirty-six-hour shifts, and that’s what they’re signing up for. You don’t become a doctor and expect an eight-to-five schedule with open-ended flexibility. The structure and expectations are clear from the start. I think companies should take the same approach. Design roles that are intense for a set period, then create off-ramps so people who want to step back can move into another part of the company where they’re still valuable, just in a different context.”

Whitehill notes that people bring different rhythms to their work, and not everyone is built for the same pace. She points out that younger, fresh-out-of-school hires often arrive already conditioned for long hours, while more seasoned employees may be balancing families, limits, and a very different kind of energy.

• AI aye aye: When asked why workplace intensity is surging, she points to the current AI wave as a financial and cultural accelerator. “This new focus on generative AI is creating a whole different mindset around culture and productivity. The funding behind these companies is on a scale we just didn’t see in earlier eras, which raises the stakes on hitting valuations and proving you can grow into them,” she says. “Generative AI is built to improve productivity and reduce how much humans need to be in the loop, so the culture ends up mirroring the thing you’re creating.”

• Optimizing the grind: But Whitehill warns that even the most willing grinders can hit diminishing returns when they work in a vacuum. Her answer is to build cultures where collaboration and shared context keep performance high. “Keep up with what your team is doing. A simple weekly activity report or lightweight check-in on what they did and what they plan to do next is enough. That ongoing collaborative conversation between a team lead and the people doing the work helps you spot when someone is putting in huge hours but not getting much output from it,” Whitehill explains. “That’s the moment to suggest a few days off or a shift to another part of the project to reset their thinking. It really comes down to maintaining that dialogue so you’re getting the best output for the effort that goes in.”

She rounds out the conversation by reiterating that while the present moment may feel uniquely intense, the pattern itself isn’t new. What can be new, however, is how leaders design systems that allow people to shift between ambition and balance without penalty.

“AI is just the current thing, and who knows what will come next. There will always be a pocket of people who want to work as hard as possible and grind for a while, and there will always be people who prefer more balance. Most of us float between those two modes over the course of a career,” Whitehill concludes. “That part isn’t any different from the past, we just have new tools that make a blended approach easier to pull off. It’ll keep evolving, and people will keep self-selecting into each lane at different points in their lives.”