Turning Chaos Into Clarity

Jennifer Cresswell never expected to start her own business.

She built her career the traditional way—studying engineering, then pivoting into finance. She helped implement Patriot Act compliance at a major credit card company. She managed the Amazon credit card portfolio. She worked her way through the ranks of some of the biggest financial institutions in the country.

But over time, the work stopped fitting.

“Corporate life started to feel like a box,” she says. “I realized I wanted more autonomy, more creativity. I wanted to build something of my own.”

She didn’t quit overnight. She took steps. First joining a smaller consulting and marketing agency, then stepping into a leadership role where she was tapped to build out the sales function—despite never having worked in sales before.

“They said, ‘We need someone to figure this out,’ and I thought, ‘Well, okay. Let’s figure it out,’” Jennifer says.

What followed was her first real taste of entrepreneurship.
She didn’t just lead. She built—strategy, pricing, go-to-market plans, hiring processes.

And she loved it.

After helping grow and sell the company, Jennifer stayed on through the acquisition—navigating one of the most complex and overlooked parts of the startup lifecycle: integration.

It wasn’t glamorous. It was messy. But it was eye-opening.

“I realized this is the part of business I love,” she says. “The messy middle. The place where you turn chaos into clarity.”

She went on to help integrate two companies, unify cultures, and steady the ship during the early months of the pandemic. By the time 2022 rolled around, she knew it was time to bet on herself.

That’s when she launched Thoughtgro—a consultancy built to help service-based founders organize their chaos, grow intentionally, and build businesses that can actually scale without breaking.

But the launch didn’t go as expected.

“I had leads lined up. Almost all of them fell through,” Jennifer says. “I had to start from scratch and build it from the ground up.”

There were moments when she questioned whether she’d made the right call. But she kept showing up.

Because she knew what she was building was needed.

Thoughtgro works with service-based businesses—often founder-led, often between $1M–$20M in revenue—who are trying to grow but are hitting real structural walls.

Jennifer doesn’t come in with a one-size-fits-all playbook.
She comes in to help founders untangle what’s working, what’s not, and what needs to change if the business is going to survive the next chapter.

Her approach is built around four pillars:

• Structure: What roles does the business need to grow—and are those roles clearly defined?

• People: Are the right people in the right seats, with clear accountability?

• Process: Are systems making life easier or just creating more bottlenecks?

• Culture: Does the team know what the company stands for, and are they aligned?

“A lot of people focus only on logic and structure,” she says. “But there’s a huge emotional component to running a business. You have to meet people where they are.”

That balance—of logic and empathy—is what sets her work apart.

It’s not about building the most sophisticated org chart.
It’s about building the right one for where the business is now—and where it’s going.

Jennifer’s work sits at the intersection of operations and emotional resilience.

She’s not just helping companies grow.
She’s helping founders get out of reaction mode and back into intentional leadership.

“You’re not going to be right 100% of the time,” she says. “But you have to keep making decisions and moving forward.”

That’s the throughline in her own story too.

She didn’t build Thoughtgro from a place of perfection.
She built it from experience. From seeing the mess up close. From knowing what founders need when the pressure’s on and the path forward isn’t obvious.

And that’s why her clients trust her.

Because she’s been there.
Because she’s done the work.
And because she knows how to help them do it too.