I recently sat down with Joel Stevenson, CEO of Yesware, on his podcast The Hard Sell. Joel and I first connected when Vendasta acquired Yesware, and we worked together during that chapter. This conversation gave me a chance to talk about something I’m deeply passionate about: what happens when you take everything you’ve learned in SaaS and channel sales and apply it to an industry most people think is dying.
Spoiler: radio isn’t dying. It’s being reinvented.
From Vendasta to Harvard Media
For those who don’t know the backstory, I spent years as the Chief Commercial Officer at Vendasta, a SaaS company that built a platform for agencies and media companies to sell digital solutions to local businesses. I also hosted the Conquer Local podcast, which became a platform for sharing lessons on local sales and marketing. That role gave me a front-row seat to how media companies were struggling to evolve.
When the opportunity came to join Harvard Media as EVP and Managing Partner, I jumped at it. Harvard Media owns radio stations across the Canadian prairies, primarily in Saskatoon. But the company I walked into wasn’t just a radio company anymore. It had already acquired a digital agency, and the mission was to merge those two worlds into a single omnichannel organization.
As I told Joel: “When I met with Brandon and we had the very first conversation about the role, it was really clear that this is a company that wants to transform from a legacy radio broadcaster into an omnichannel media company.”
Why Radio Still Matters (But Not in the Way You Think)
Here’s the thing most people get wrong about radio. They think it’s just the transmitter on the stick in the field, the AM/FM signal. And yes, that’s part of it. But what people miss is the content.
Radio stations produce an enormous amount of local content every single day. At Harvard Media, our teams are out in the community covering events, conducting interviews, creating stories. The problem was that we were only delivering that content through one channel: the traditional broadcast signal.
Meanwhile, streaming audio is growing rapidly. Apple, Spotify, Amazon are all competing for ears. Programmatic audio is eating into traditional ad budgets. The shift was clear: we had to take the content we already produce and repurpose how it gets delivered, through mobile apps, websites, social channels, and streaming platforms.
Joel made a sharp observation during our conversation. He noted that the radio industry tends to be “myopically focused on their own universe” rather than looking at the broader competitive landscape. That resonated with me, because one of the first things I did at Harvard Media was upgrade our tech stack on apps and websites so we could publish content in real time, not just broadcast it over the airwaves.
The Transition from Channel Sales to Direct Sales
Joel asked me a question that really made me think: having spent years selling through a channel at Vendasta, what’s different about selling directly to end customers?
At Vendasta, we sold through partners. Those partners owned the customer relationship. My job was to enable them, train them, and give them the tools to succeed. It was a layer removed from the actual business owner.
At Harvard Media, I have 42 sales reps on the street who go face to face with local business owners every day. And here’s what I realized: I actually think of those reps as my channel. They have the relationship with the customer. A really good media salesperson is a trusted advisor to that business owner. They’re not just selling ads. They’re helping with websites, digital advertising, SEO, social media, and reputation management.
The big shift? In the old model, if a client didn’t need the audience your station had, the answer was just “no.” It was binary. Now, we go in to truly help the business owner with their problems, and radio might be just one piece of a broader portfolio. We can offer them everything from streaming audio to display ads to social media management. That changes the entire dynamic of the sales conversation.
What I Learned About the “Binary Challenge” in Media Sales
I lived this binary challenge in my early days of selling. If the client didn’t believe in your format or didn’t need your specific audience, the answer was a hard no. Then you had to do a bunch of what I call “sales ships” to try and turn that no into a yes. But if it doesn’t fit, it doesn’t fit.
Now the conversation is completely different. When I walk into a business, I’m not asking them to buy a radio ad. I’m asking them what their biggest challenges are. Maybe they need help with their Google presence. Maybe their website is outdated. Maybe they need a cohesive digital advertising strategy. Radio becomes one tool in a much larger toolbox.
This is the exact same shift that was happening across the media landscape at Vendasta. We saw hundreds of media companies going through this transformation. The difference now is that I’m living it from the inside.
Building a Four-Generation Sales Team
One of the most fascinating things about leading Harvard Media’s sales organization is the generational diversity. I have four generations of sellers working together: people late in their careers who built their success on handshake deals and relationship selling, and younger reps who are digital natives comfortable with programmatic advertising and social media campaigns.
During my first 120 days, I went and met everyone in the organization. The generational dynamic came through loud and clear. Some of the legacy radio sellers were resistant to learning digital, while some of the digital team members didn’t fully appreciate the power of broadcast relationships.
The key was creating an environment where all four generations can collaborate and appreciate what each brings to the table. The younger talent is often more tech-savvy and adaptable, but that’s not always the case. Some of them like to stay in their lane too. The experienced sellers bring decades of client relationships and a deep understanding of local markets. Both are valuable.
As I explained to Joel, we had a digital agency that was merged into a radio company, and the plan was to bring it all together into one omnichannel organization. “But it’s not that easy because of the legacy,” I said. Some people late in their career don’t necessarily want to go back to school three days a week to learn programmatic advertising.
The Content Opportunity That Most Media Companies Miss
Here’s something I got really excited about when I joined Harvard Media. We have content creators in the building every single day, our on-air talent. These people are already producing compelling local content. The opportunity is to take that content and distribute it beyond the traditional broadcast.
We started writing pieces of content and publishing them to our apps and websites in real time. If we’re covering a local event in the community, talking about something happening in Saskatoon that weekend, that content doesn’t just live on the radio. It goes on our website, our social channels, and our app.
We also rolled out a completely new digital platform that we call “reimagining interactive.” It’s a new way for our audience to engage with our brands beyond the dial. This is the future of radio: it’s not about the signal, it’s about the content and how many places you can put it.
Lessons for Anyone Making a Career Transition
Joel and I talked about the courage it takes to make a big career move, especially later in your career. I left a senior role at a SaaS company to join a radio company. On paper, some people thought that was a step backward. But I saw it as a step into a massive transformation opportunity.
Here are the principles that guided my transition:
- Follow the problem, not the hype. Everyone was chasing pure SaaS plays. I saw an industry with incredible content assets that just needed a better go-to-market strategy.
- Your past experience compounds. Everything I learned building channel programs at Vendasta directly applies to building a modern media sales organization. The playbook is surprisingly similar.
- Culture is the hardest part of transformation. Technology is the easy part. Getting people aligned and excited about a new vision is where the real work happens.
- Be willing to be a student again. I walked into Harvard Media and immediately started learning from people who have spent decades in the radio business. Those folks teach me things every day.
The Bottom Line
My conversation with Joel reminded me why I love this work. Whether you’re selling SaaS through a channel or selling media solutions directly to local business owners, the fundamentals don’t change. Understand your customer’s problems, build trust, and deliver real value.
The radio industry is going through one of the most significant transformations in its history. If you’re someone who thinks radio is dead, I’d challenge you to look closer. The companies that figure out how to take their content beyond the transmitter, the ones that build truly omnichannel media organizations, are going to win.
That’s the bet I’m making at Harvard Media. And I’ve never been more energized about a challenge in my career.
You can listen to the full episode on The Hard Sell podcast by Yesware.