Rebecca Smith came to M&A from the other side of the table, as a founder navigating the sale of her own company. That experience now shapes every deal she leads. She knows what it’s like to tie your identity to a business. She knows the weight of letting it go. That experience isn’t just part of her story, it’s the reason clients trust her with theirs.
“I’ve sat in the founder’s seat,” she says. “I’ve felt the hope, the fear, the doubt, all of it. That’s why I show up with both strategy and empathy. Every single time.”
Before joining Raincatcher, Rebecca spent years in deal-making, first in the Main Street market, then in SaaS, and eventually in full M&A leadership. Along the way, she became a sought-after exit planning coach, guiding founders not just toward a number, but toward clarity, confidence, and readiness.
Her north star is always the same: helping people make one of the biggest decisions of their lives and feel good about how they got there.
“This work is deeply human,” she says. “Founders often don’t expect how emotional it becomes. When buyers start digging into every line item, it can feel quite invasive, even when it’s just business. My job is to prepare people for that. Not just with documents and data, but with mindset and support.”
Rebecca brings a rare balance to her deals: glass-half-full optimism paired with sharp, grounded realism. She believes every great transaction starts with understanding the “Why?” The retirement dream, the next venture, the deeper purpose that’s pulling an owner forward. She keeps that vision in focus, even when the process gets complex.
“I always think about the day after the deal,” she says. “Are they proud of how it happened? Are they excited for what’s next? That’s the story I want to help them write.”
For Rebecca, Raincatcher brought together the right mix: strategic minds, down-to-earth people, and a mission that matched her own. “I’d watched them win at an M&A conference years ago, and I remember thinking, they do things differently. Now I get to win with them and I feel lucky every day.”
Outside the deal room, Rebecca is still building. She’s a founder at heart, constantly ideating and creating through her ventures, Thrifty and bundl. But her proudest title is Mom to Bella, a college senior, and Scout, a competitive volleyball player.
When clients work with Rebecca, they get more than an advisor. They get an experienced guide who brings clarity, steadiness, and care to every stage of the deal, with the goal of not just closing, but creating a future her clients can truly look forward to.
Thinking about your next chapter? Connect with Rebecca to explore what a successful and meaningful exit could look like for you.
