In April 2019, I booked an Airbnb “farm tour” experience just outside of Nashville—a break from our family vacation and the city’s constant energy. We drove through rolling tobacco fields and winding back roads until we reached a quiet Tennessee town. Our guide, Jennifer, a lifelong local, led us to a no-frills diner—the kind with metal trays and cafeteria-style serving. Collard greens and fried green tomatoes. Sweet tea in styrofoam cups.

As we settled into our table, Jennifer asked what I did for work.

And I paused.

I’d spent two decades leading digital and social media for some of the world’s biggest brands (Microsoft, Qualcomm, Adidas, Nestle). But in that moment, I felt uneasy saying it out loud.

It felt… complicit.

Like I was part of something that had gotten off course.

That year, social media usage had topped two hours a day. Half of young adults in the U.S. were online almost constantly. Cyberbullying was up. The suicide rate for high school girls had increased by 65% since 2010. The very platforms that once promised connection were now fueling comparison, anxiety, and division.

I changed the subject. But I didn’t forget the feeling.

That was the moment I knew I needed to write a new chapter.

Our Farm Tour


Back in 2016, I’d launched a pilot program helping C-suite leaders find their voice online. It wasn’t about PR polish or performative posting. It was about showing up with humanity. I loved that work—being a trusted advisor, helping leaders share their story, and putting some good back into a digital space that desperately needed it.

Fast forward to 2024: I left big tech, saved two years of salary, and launched Co-pilot Communications. Today, I help senior executives and ambitious founders show up online (social, podcasting, web) —not as perfect personas, but as real people with something meaningful to say.

At Co-pilot, I work with leaders of integrity, curiosity, and humility. Together, we’re cutting through the noise, rejecting the algorithmic sameness, and reintroducing the kind of communication that builds trust, human connection, and reminds us what it means to be social.

Because a digital brand isn’t optional anymore. In fact, showing up as yourself is your greatest differentiator.

Although, the digital landscape has changed rapidly over the course of my career, I still believe that the best flight plans always starts with good communication.

And a great co-pilot.


Jess Jensen