Rich Whipkey
President & Founder


Waybetter’s founder, Rich Whipkey, embarked on his professional career in the thick of the dotcom boom—that strange, exciting, and frequently confusing era when technology was evolving faster than any of us knew what to do with it. For people who lacked curiosity and a sense of adventure, it was all a bit unsettling.

But for guys like Rich—curious, intrepid, engaged—the changing landscape was a place to explore and learn new things. Rich, an entrepreneur at heart, successfully launched multiple startups, including an on-demand digital print house where he helped clients personalize and coordinate their marketing efforts across multiple channels.

As a technology junky, the new tools inspired Rich, but he was also frequently frustrated that so many of his clients failed to grasp how truly powerful it all could be (or how much success they could have) if they took a step back to think about process and strategy before turning on their powerful machines.

That gut-level instinct is how Waybetter got its start. And it has remained our foundation ever since: at our core, we have a passion for great technology, a fierce commitment to bulletproof strategy, and a dogged belief that everything can get way better if you think strategically, choose the best tools for the job, and then work really, really hard.

In its infancy, Rich steered Waybetter to the industries his old clients populated: financial services, healthcare, and retail. Then, a twist of fate put him in touch with the marketing team at a highly ranked university in Washington, D.C. that was struggling to enroll students in one of its summer programs. Rich—knowing literally nothing about higher ed enrollment—put everything he’d learned in the “real world” about personalized, multichannel communications and marketing to work. Revenue for that university’s one program went up $1,000,000 over the previous year. 

The rest, as they say, is history. 

Today, Waybetter works exclusively with colleges and universities and has clients across the higher ed landscape. We work for schools in the Ivy League, at universities in Boston, Washington, D.C., and Philadelphia, at colleges in Pennsylvania, Ohio, Michigan, Kansas, Hawaii and everywhere in between.

Despite Waybetter’s growth, Rich is actively involved in every single client’s strategy and process—from search name buys to brainstorming email subject lines at weekly writing sessions.  Nobody knows more—or cares as much—about successful higher ed enrollment practices than he does. Of that he makes very, very certain.