A Channel Stopped Working, So He Built a New One

Ryan O’Hara didn’t plan on starting a new category in sales. He just couldn’t stop noticing how broken the old ones were.

For the last 15 years, Ryan’s been on the front lines of B2B go-to-market—cold emailing, cold calling, launching creative stunts, and building sales playbooks from scratch. But sometime around 2021, things started to feel… off.

“I’d been running this annual survey at LeadIQ called the State of Prospecting,” he says. “In 2016, you’d get a 6% reply rate on a cold email. In 2021, it dropped to 1–2%. Same with cold calls—used to be 10% connect rate, then it was 3%.”

That’s not a slight dip. That’s a complete collapse of the old playbook.

“And no one was doing anything about it, so I started to ask—what would a new prospecting channel actually look like?”

The result is Pitchfire, a startup that Ryan co-founded to create something completely new: paid prospecting.

Here’s how it works: instead of hammering strangers with unsolicited sales pitches and hoping for a 1% response rate, you pay people to reply. Literally.

On Pitchfire, buyers install a plugin and receive offers from sellers who want to pitch them. If the buyer is interested, they accept the pitch, get compensated, and everyone’s expectations are clear. Sellers get responses. Buyers get respect—and cash. Pitchfire takes a cut.

It flips the power dynamic. And it’s working.

“Last month, we sent out 51,000 paid pitches,” Ryan says. “That’s resulted in 2,700 users and $25,000 paid out to buyers.”

But the journey to Pitchfire started way earlier—long before the idea, the traction, or even the first prototype.

It started with Doom.

“I used to go to work with my dad on the weekends,” Ryan says. “He worked in early internet companies as a network engineer, and my brother and I would play Doom on their LAN network while everyone worked.”

His dad never finished college, but worked his way into tech anyway. Watching him build a career in startups planted a seed.

“I think it made me believe that startups were possible for people like me,” Ryan says. “Like, you didn’t need a perfect pedigree.”

That belief led him to a startup while he was still in college—a managed DNS company that pitched a problem to Ryan’s marketing class. While most students chose on-campus orgs for their project, Ryan picked the tech company 40 minutes away.

“I was like, they’re in internet and tech, and they don’t have a YouTube channel. So I started filming videos around the office and posting them. I didn’t even know video editing before that—just learned it on the fly.”

After the semester ended, they hired him. At first, it was to keep making videos. Then, to cold call.

That’s when Ryan found his lane.

“I was told to just be myself—stop copying the AEs who hadn’t prospected in 10 years,” he says. “So I started doing weird stuff. Pop culture references. Music videos for prospects. One of them went viral.”

That video? It was a personalized prospecting campaign to the CEO of Hulu. He forwarded it to his press list. Ryan got written up across the web.

“I couldn’t go back to regular sales after that,” he laughs.

The company moved him into a hybrid role—half training reps, half running wild marketing experiments. He flew to speak at startup accelerators, taught guerrilla marketing, and got recruited by one of those companies to help raise money. That led to his first real startup attempt. It failed.

But he needed it.

“You have to eat sh*t once,” Ryan says. “It’s a rite of passage. It teaches you what not to do next time.”

After that, he joined LeadIQ as the first business hire. Over seven years, he scaled the company from near-zero to 30,000 users and helped them raise over $40 million in VC funding. But in the background, that same question kept nagging at him:

Why is prospecting so broken—and why isn’t anyone fixing it?

So he left.

At first, Pitchfire was a marketplace for booking meetings. But it didn’t feel right. “Sellers felt like they had to fake interest. Buyers felt awkward getting paid and then saying no. No one was being real.”

They pivoted.

Now, Pitchfire operates more like a dynamic inbox plugin. If a buyer receives a cold email, the plugin routes it to Pitchfire. The seller can then pay to send a pitch. The buyer gets paid if they respond. And Pitchfire gets a cut.

It’s more transparent. More human. And way more efficient.

“Traditional prospecting takes 220 touches to get a meeting,” Ryan says. “With Pitchfire, it takes three.”

The idea is gaining traction, but Ryan knows they’re still early.

“We want 100,000 people in the marketplace,” he says. “We want everyone who cold emails someone to be told, ‘Cool—but go through Pitchfire.’ That’s when this gets really interesting.”

They’re already layering on services—like helping companies run webinars or events and using paid pitches to re-engage those leads. They’re building the infrastructure for a new kind of go-to-market.

Ryan isn’t here to replace marketing or sales. He just wants to make both better. More honest. More efficient. More fair.

“When you think about it, B2B companies already spend thousands trying to reach people. Why not just give that money to the people you're trying to reach?”

That’s not just a better pitch. It’s a better way to sell.

Want to hear more stories about founders like you? Subscribe to our newsletter