travel advisor

    I left a successful sales career to sell something I actually believe in

    By Eric RileyAugust 2026
    I left a successful sales career to sell something I actually believe in

    I built an entire sales market in Tampa for a roofing and solar company, from nothing. Trained a few people, one who became the second highest producer in the whole company. I was number one. And I watched the business slowly choke on its own success because leadership was too scared to build the infrastructure to support what we'd built.

    Lead times stretched out so long we started losing business we'd already closed. I knew exactly what needed to happen. Bring in more crews, more project managers, invest in the pipeline we'd created. I said so. Nothing changed. Eventually I walked away, not because I stopped being good at sales, but because I was tired of being right about a problem I had no authority to fix.

    That wasn't a one time thing either. Fifteen years across automotive, roofing, and solar, and the same pattern kept showing up. I'd find knowledge gaps in these businesses that even leadership hadn't caught. I could see the fix. I just didn't own the business, and I had no real interest in owning those businesses. I just wanted the ones I worked for to take the next step. Most of the time, they didn't.

    Why the sales stopped feeling like the point

    None of this is a knock on the people I worked for. I don't think that way and I'm not interested in writing that way. But after enough years of seeing a fix and watching it get ignored, the drive to keep selling for a business like that just wears down. I had built enough of a career to provide for my family. So I stopped, and I sat with the question of what came next.

    The training class that changed the direction

    My wife Sarah started as a stay at home mom. When our kids got old enough, she went back to work, and that work became travel. She built Travel Squad Vacations into a top 150 agency out of more than 13,000 advisors nationwide, alongside our teammate Melissa. I watched her build that from the ground up over years.

    I had a few different business opportunities in front of me around that same time, and every one of them kept hitting roadblocks right when I felt close to turning the corner. I was praying about it, genuinely asking for direction, because I couldn't tell which door was actually open.

    Then Sarah and I sat in a training class on business and marketing in the travel industry. And it clicked. Everything Sarah and Melissa had spent years building, the sales instincts, the client relationships, the industry credibility, I didn't have to build any of that from scratch. I just had to learn the nuances of an industry I'd been watching up close for years.

    What I'm actually bringing to this

    I'm not learning how to sell. I spent 15 years doing that at a high level, plus 8 and a half years before that as a boat mechanic, which is its own kind of problem solving most people in this industry have never had to do. What I'm building now is the infrastructure side, the tech, the systems, the business to business relationships, specifically around incentive travel and expedition travel. The exact kind of infrastructure I kept asking my old employers to build and kept getting told no.

    This time I'm not asking permission. I'm the one building it.

    What this actually means if you book with me

    Here's the thing I want you to know if you're considering booking a trip through me. I'm not looking at your trip as another number in a cash register. I'm booking it the way I'd want someone to book mine.

    That means real questions before anything gets quoted. What matters to you on this trip. Who you're trying to impress if it's a corporate event. What kind of experience you actually want your team to walk away with if it's an incentive trip. I'm not filling out a form. I'm listening, and then I'm building the trip around what you actually told me, not around what's easiest to sell.

    I didn't leave a good sales career to do this halfway. I left it because I wanted to be in an industry where doing right by the client and building something real were finally the same job. That's the whole reason I'm here.

    • About the Author

    Written by Eric Riley, advisor at Travel Squad Vacations.

    Read Eric's profile →
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