Capitol Communicators: Profile of Raymond Crosby, CEO, Crosby Marketing, Annapolis, MD

Capitol Communicators is a profile series spotlighting the people shaping the present
and future of advertising, digital, marketing and public relations in the Mid-Atlantic.
This profile features Raymond Crosby,  CEO, Crosby Marketing, Annapolis, MD

Raymond Crosby knows a lot about change and re-invention. Crosby Marketing has been constantly evolving over its 50+-year history. His father, Ralph, started it in 1973, buying a tourist publication company called Rambling Through, which became PR Associates, and later Crosby Marketing. Raymond, who was the firm’s third employee, now leads a team of over 100, and an agency that is constantly cited as a local and national leader, ranking in the top 25 of O’Dwyer’s independent PR firms list, with over $30 million annually in fee income. He credits the agency’s success with its continuing evolution, changing just as communication does, and says he learns something new every day.

Crosby Marketing has consistently been named a local Top Workplace, and Raymond recognized as a Top CEO. It’s been said that “culture eats strategy for breakfast,” and Crosby has been able to foster both a winning culture and effective business strategy. One secret may be what he calls the “no jerks policy,” another may be the focus on giving back to the community, with annual volunteer days and a scholarship program at Anne Arundel Community College. The firm’s clients include Peace Corps, DAV (Disabled American Veterans), Shriners Children’s Hospitals and the Social Security Administration.

Raymond, please tell us about yourself.

I’m the CEO of Crosby Marketing, leading our team to fulfill our mission on Inspiring Actions That Matter. We work with leading nonprofits and causes, health care organizations and federal agencies, focusing on purpose-driven work that builds our client’s mission and business impact, while improving people’s lives. It’s really rewarding work.

What are the things you are most proud of?

On the work side, growing Crosby from a small local firm into a nationally recognized agency with a great team of passionate people. We’ve been named a Best Workplace by the Washington Post for 9 straight years, and our client tenure is triple the industry average. On the personal side, I’m super proud of my family and extended family. We’re a tight bunch and there’s lots of love and support to go around.

What are the most significant changes or trends you see happening in the communications industry in 2026?? How are you dealing with it?

The constantly evolving media landscape, the challenge of building brand trust in today’s climate, and the opportunities to leverage AI are all driving rapid change. We have a Crosby 5.0 strategic plan that is guiding our investments in talent and technologies to continually evolve the firm, help clients connect the dots, and optimize marketing performance.

Would you share a “lesson in leadership”? As the leader of the agency, how did you develop the strategic plan? And how do you engage your team in bringing it to life?

As a leader, you have to constantly be thinking about what’s next down the road. I lean heavily on our Executive Committee and key thought leaders on staff to help inform and shape our plans for Crosby. I’m a big proponent of the adage: If you want to go fast, go alone. If you want to go far, go together.

What are the skills that are necessary to be successful today?

Being curious, up to date with culture, and constantly learning the craft of marketing. I’d also say having the grit to fight through adversity will serve you well.

What tools should we be using to be successful?

More than anything, our ears. Listening more carefully to understand our client’s challenges, the marketplace, and our audiences. Technology is a great enabler, but we’re still in the business of understanding human behavior and touching people’s hearts.

Who do you most admire and why?

My father, Ralph. He’s a self-made man with great integrity, a lifelong entrepreneur, an author of four books, a philanthropist, and an extraordinary father and grandfather. From very humble beginnings, he’s created an amazing life and legacy (and my mom Carlotta had a lot to do with that, too!).

What advice helped you most in your career, and is that advice still relevant today?

My college lacrosse locker room had a memorable sign that read, “Nobody ever drowned in sweat.” I’m a big believer in plain old hard work. If you want to learn, grow, and succeed, it’s on you to make it happen. There aren’t any shortcuts.

What keeps you up at night? And what brings you joy during the day?

The state of our country worries me most. We have become way too polarized and need focus on our stronger common purpose. Lots of things bring me joy during the day: simple stuff like a great cup of coffee or binging a new show with my wife.

Any streaming recommendations for us?

We’re right in the thick of watching Landman and highly recommend it.

What’s the coolest thing you’ve ever done?

Probably hiking along an active volcano in Iceland or traversing a glacier in Norway.

Capitol Communicators profiles allow you to meet some of the most interesting
and insightful prosin our region, learn how they stay ahead of the curve
and gain practical wisdom during a time of constant change.