Redirecting.work

and technology. He also ran regional tech roadshows and co-founded research collaborations. Yet most of these projects had a shelf life. “Many were two- or three-year experiments,” he admits. “They started strong and then either ran out of steam or money.” The life was volatile—creative and thrilling—but also financially erratic and demanding for his family.

 

Sumser now attributes his constant reinvention to something he only recently discovered about himself: ADHD. “It explains a lot,” he notes. “The curiosity, the restlessness, the cycles of building and unraveling.” His work life was rich with insight but also unpredictable. “The cash flow was volatile,” he says, “and that was always a pressure.”

 

So, when the COVID-19 pandemic caused another industry downturn, he made a surprising choice: he became an employee.

 

Current Role: Leading with Language at Salary.com

 

For now, Sumser serves as Vice President of Marketing (Content) at Salary.com—a shift from independent pundit to organizational team player. This move wasn’t linear. First, he pitched a job search video series that was completed but never released. Then he ran a job board initiative. Finally, he landed in a leadership role focused on creating content strategy for a niche and complex domain: compensation.

 

He says, “I knew very little about the day to day realities of the compensation management function. It became clear to me that compensation is the throughline in all HR functions. It’s the heartbeat of the organization. It’s the place where the exchange of created value for capital value happens. When coherently processed, compensation data forms the spine of all organizational data. We are just beginning to see the power of well-manicured compensation information.”

 

His impact has been substantial. He built a content team in the Philippines, crafting processes to bridge cultural and communication divides. He set strict standards for accessibility, insisting that all content be written at a 10th-grade reading level. “I want our writing to be consumed, not admired,” he explains. “It’s about meeting people at their level of need.”

 

Drilling further into his readability standards, over the years, John developed a distinctive discipline around writing—publishing a daily column for 15 years that helped shape how the digital recruiting industry talked about itself. He didn’t write to impress; he wrote to be understood. Influenced by the military's readability standards and his own experience in simplifying complex systems, he honed a writing style that favored short, clear sentences that were approachable but never condescending. “My gift,” he says, “is taking complicated ideas and making them understandable.” That clarity of thought became both his brand and his personal research lab, fueling a virtuous cycle of experimentation, insight, and continuous learning.

 

Sumser brings a signature skill to every project—distilling complexity into clarity. “That’s what made me a good engineer, a good analyst, and now a good marketing leader. It’s the ability to translate complicated things into something useful.”

 

The shift to being an employee hasn’t always been easy. “When you go from a solo role to being inside a hierarchy, it’s like the laws of physics change,” he says. “You don’t control your time. You can’t always steer the boat. And that’s a hard thing for someone who’s used to independence.”

 

Still, he’s grateful. He has a steady paycheck, a creative role, and deep professional partnerships. “I love what I do and the people I do it with,” he says.  Most importantly, he’s learning again—about leadership, about how to manage globally distributed teams, about the difference between what tech looks like and how it’s built, and especially, about himself.

 

Advice for Others: Expect to Stub Your Toe

 

Sumser’s guidance to others making the leap from solo entrepreneurship to salaried work is clear: “Don’t expect it to be smooth.” He compares the transition to moving from one planet to another, where gravity shifts and the language changes. “You can’t imagine what it’s going to be like. You just have to experience it and learn through the bumps.”

 

One key to success, he says, is to interrogate your assumptions. “I assumed that my ideas would always be welcomed," he laughs. But that assumption comes from being an analyst and having the stage. As an employee, people push back. "I had moments where I thought, ‘But this looked so easy from the outside.’ That was humbling.”

 

Support systems are also essential. Sumser's support system includes his long-time partner, Heather, the company’s CEO, his friends and colleagues in the Marketing group, and a small, trusted network he calls his “board of advisors.” These twenty or so individuals, from various parts of his life, provide critical feedback and perspective. “I don’t do big decisions alone,” he says. “This group keeps me honest.”

 

Finally, he emphasizes that transitions are not just about what you do—but about who you are. “You have to learn the physics of a new culture. And in doing so, you may learn something new about yourself.”

 

Who Knows What's Next?

Though thriving at Salary.com, Sumser can imagine another pivot down the line. Things are shifting fast in tech and in the world. His experimenter's mindset has reawakened. “The only thing I hate worse than a steep learning curve is not being on one,” he says. “With senior leadership experience, I have a whole new perspective on both what's possible and the challenges of actually making it happen.” If there's another pivot, the move will be informed by all that he's learned about structure, collaboration, and writing for impact.

 

His life remains an evolving lab—each phase building on the last, each pivot a path to the next.