Chief launches Oregon Trail-style corporate ladder game

Every elder millennial probably remembers the sheer stress of playing Oregon Trail in the ’90s. Traversing the country in spite of bad weather, animal attacks, and broken-down wagons, only to end up dying from dysentery before reaching the finish line.

Now, imagine playing that game in your late 30s, but make it corporate.

That’s what Chief just did with a new free game dubbed The Corporate Trail. Players navigate their own corporate journeys, earning points for likeability and well-being along the way. They can choose from four different departments—tech, marketing, operations, and, of course, HR—and play through scenarios like taking on more mentees and skipping a family event to handle a work crisis. But wait! There are also traps that lead to burnout, and inevitably, falling off the corporate ladder.

The game might seem a bit cringe at first, but the makers at Chief, a women’s forum for budding executives, said it’s meant to show the tightrope that women have to walk as they advance their careers.

Women face several challenges at different levels of their careers. They have less representation in higher ranks, and account for less than 30% of the C-suite, according to McKinsey. Completing The Corporate Trail isn’t meant to be the end but rather the beginning of a conversation, according to Trey Boynton, chief diversity and people officer at Chief—who said women constantly have to balance being too aggressive or too nice, and are held to a different standard in business.

“Men just don’t have to encounter the same questions about their leadership [or] the same judgments about their leadership,” she told HR Brew. “As an HR leader…what I want to always talk about is, how are we actually taking this and starting a solution around what we know are the dynamics of the workplace.”

Women’s progress in the workplace has stalled in recent years, according to a 2024 report from Deloitte. HR leaders should work with other executives to find new pathways around the barriers, “offering solutions and interventions, work streams, initiatives to counterbalance what we know to be true,” Boynton said. She hopes that the simulation will cause leaders to think about the societal biases many people face so they can adjust their policies accordingly so everyone is empowered to do their best work.

“When we offer health and well-being offerings, strategies [and] support systems, people are more likely to be productive,” Boynton said. “You also then have to be super open to understanding the unique needs of all of your team members, because each person is going to experience them differently, and we need to include men, trans, non-binary folks in this conversation.”