Building and Selling a Digital Marketing Agency: Lessons from Kim Grennan

Building and selling a digital marketing agency is rarely a straight path. It’s a journey filled with unexpected turns, strategic moves, and lessons that only come from experience. In a recent podcast episode, Kim Grennan shared how she built, scaled, and sold multiple agencies over nine years—offering a roadmap for entrepreneurs who want to grow service-based businesses with a potential exit in mind.

From Finance to Marketing Entrepreneur

Kim didn’t start with a marketing background. With a degree in economics and experience in investment banking and Verizon’s M&A team, she entered marketing almost by accident. While working with startups, clients kept asking for marketing help.

Despite having little hands-on experience, Kim leaned into it:

“I didn’t have any background in it. I just watched a lot of YouTube videos, looked at some online courses, consumed as much information as possible.”

Her willingness to learn, adapt, and take risks became the foundation of her success.

A Bold Client Acquisition Strategy

What set Kim apart was her approach to winning clients. Instead of binding them to long contracts, she made an unusual offer: work with her for free during the first month.

“If you don’t like working with us for whatever reason, you don’t owe us a thing—we could walk away.”

The result? Not a single client walked away. This no-risk approach quickly built trust, secured recurring contracts, and created a foundation of long-term relationships that made her agency more valuable to buyers.

Scaling Beyond the Founder

Growth brought challenges. As clients multiplied, Kim hired freelancers and contractors, eventually bringing on full-time employees once she hit $500,000 in annual revenue.

At the million-dollar mark, she made a pivotal move: hiring a general manager.

“I knew for exit planning, I couldn’t be that owner-operator who was in there every single day. That’s just not as valuable to buyers.”

By removing herself from daily operations, Kim made the business scalable and sellable.

Cold Email Outreach as a Growth Engine

One of Kim’s most effective strategies was cold email outreach. She became so skilled at it that clients began asking her to run it for their businesses, leading her to launch Leadstrike, a separate service she later sold just two months after exiting her main agency, Axel8.

For B2B businesses, she champions cold email as a cost-effective, controllable, and scalable alternative to paid ads—when executed correctly.

The Hard Truth About Selling

Selling, however, was far from seamless. Kim stresses the importance of having the right advisors, especially brokers who properly vet buyers.

Her own journey involved failed deals and wasted months due to unqualified buyers, ultimately lowering her business valuation.

“There are so many things that the broker could have done to help facilitate and ensure that these things weren’t happening.”

Her experience underscores how critical experienced guidance is during the exit process.

Building With the Exit in Mind

Kim’s story is a reminder that a successful exit doesn’t start at the finish line—it starts on day one. Recurring revenue, operational systems, and founder independence all make a business more attractive to buyers.

Her path wasn’t perfect, but her persistence, adaptability, and strategic decisions turned her vision into reality—and created lasting value.