The Roles Stopped Fitting. So He Made His Own.

Michael Raab didn’t plan to start a business. In fact, for most of his 20-year career in ed tech, he did everything but that.

He ran customer success teams. Led support and operations. Helped build account management from scratch. If it touched the customer lifecycle, he did it. The only thing he didn’t do was sell—which makes it all the more impressive that now, as the founder of Raab Insight Consulting, he’s in the thick of it: prospecting, pitching, and closing his own clients from day one.

“I’ve never been in direct sales before,” he says. “But now I’m writing the messaging, doing the outreach, and having the conversations. And weirdly? I actually like it.”

It took a while to get here. After years at companies like Blackboard, Interfolio, and Docebo, the last few rounds of layoffs pushed him to rethink what he actually wanted to do. His resume was solid. His experience lined up. But after getting auto-rejected from a job that was a 95% match, he realized something had to change.

“I looked at that job description and thought—this is me. But I got a no in less than 24 hours. I knew no one even read it,” he says. “That’s when I said: maybe it’s time to try something different.”

He started building. Every morning, he'd hit the gym, then come home and brainstorm. He mapped out potential clients, wrote rough drafts of messaging, created a Google Site, and rewrote it when he realized it just sounded like his resume. He joined Slack groups. Took workshops. Networked like crazy. Slowly, it started to click.

Raab Insight Consulting was born.

The focus? Helping early-stage SaaS companies tighten the connective tissue across customer success, revenue operations, and post-sale delivery. He’d spent decades watching growing companies trip over the same operational gaps. Now, he helps them avoid it.

“I saw how these gaps in process and communication cost real money,” he says. “I knew I could help early-stage teams build it better.”

The first few months were classic Year One founder stuff: trying different outreach tactics, fiddling with messaging, wondering if anything was landing. But then the first client said yes. Then another. It wasn’t an overnight success story—but it was real traction.

And more than anything, it gave him energy. “I started to feel this momentum. Even when people said ‘not right now,’ they were interested. They remembered me. And they introduced me to others,” he says.

He’s doing things in reverse from most founders. Instead of relying on a network for referrals and scrambling to sell a year in, Michael is grinding through cold outreach from the jump. Building a pipeline the hard way, on purpose.

“Everyone says the early work comes through referrals. But I didn’t want to drain my network. I wanted to figure out how to do this myself.”

And the clients he has worked with? They’re not just projects. They’re people. One of his first consulting relationships involved helping a brand-new customer success manager who was overwhelmed and under-resourced. Michael didn’t just hand her a playbook—he helped her believe she could run it. “She called me her professional therapist,” he laughs. “I just gave her space. And helped her feel confident doing the job.”

That’s the kind of impact that drives him. It’s not just about revenue ops and retention metrics—it’s about helping real people succeed in hard roles, inside early-stage companies that are still figuring things out.

Michael doesn’t see himself as a guru. He’s a systems thinker. A problem solver. Someone who’s more comfortable in the background helping the engine run cleanly. But now that he’s running his own show, he’s realizing that people trust him not because he talks the loudest—but because he listens.

“It’s a little nerve-wracking being out here on the ledge,” he says. “But I know I have something valuable. And I’m excited to help more companies see that.”

He might not have chosen the solo path if things had gone differently. But now that he’s here, he’s not turning back.

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