Two Acquisitions, One MBA, and a New Chapter That Feels Right

Chelsey Reynolds didn’t set out to build a business. She just wanted to escape the suffocating red tape of a global corporation.

After back-to-back acquisitions, years of building sales, marketing, and customer success teams from scratch, and an MBA earned during nights and weekends, she found herself in unfamiliar territory: restless, overqualified, and deeply uninspired.

“I started moonlighting with early-stage founders. They were in incubators, had scrappy ideas, and didn’t know where to start,” she says. “And I realized people would pay me to help. I thought, this could be my job.”

That realization sparked the launch of two ventures. One that pays the bills. One that feeds the soul.

She Was Selling Necklaces on the Beach at 10

Chelsey’s entrepreneurial instincts kicked in early. Her cousins had the lemonade stand locked down, so she carved her own path—stringing together beaded necklaces and selling them up and down the beach.

“I had them all up my arm, walking the shoreline like a little mobile storefront,” she laughs.

Later, she became a BDR making 80 cold calls a day. She was just trying to survive. Instead, she rewrote the script. Literally.

“I created a flowchart for calls. If they said this, you said that. Verizon ended up rolling it out across the whole North America division I worked in,” she says. “But getting promoted was still slow. So I left.”

She took a pay cut to join a four-person startup that barely had a functioning CRM. That decision changed everything.

She Built the Team. Then the Playbook. Then the Whole Machine.

At that startup, there were no specialists. So Chelsey became one.

She taught herself HubSpot, wrote landing pages, built the social strategy, managed the sales team, launched the customer success function, and figured out how to make all the parts work together.

They bootstrapped until an acquisition came in 2020. Then things got bigger. Fast.

“We became one of 10 companies in a rollup. I was bored staying in one lane, so I asked for more,” she says.

Soon, she was running marketing, sales, and customer success across all 10 brands. She unified comp plans, merged CRMs, standardized revenue tracking, created retention strategies, and helped lead a full rebrand.

And then that rollup got acquired too.

She Helped Drive a $230 Million Exit. Then She Hit Pause.

Chelsey spent three years sprinting through a transformation that took her from cold calls to executive leadership.

“I don’t buy into that idea that the team who gets you to $1 million can’t get you to $10 million,” she says. “We proved otherwise. They invested in us.”

Fractional leaders taught her comp strategy, marketing fundamentals, finance modeling. She studied hard. Then studied more. “I got my MBA on nights and weekends because I wanted to belong in the room.”

By 2023, the company had sold again. Chelsey had leveled up, burned out, and started looking for the exit.

“I didn’t know where else to go. I just knew I couldn’t stay.”

The Asterios Group Pays the Bills. The Growth Department Builds the Future.

Her first business, The Asterios Group, is a fractional leadership network. It’s steady, profitable, and intentionally unscalable.

“We pop in to help companies fix their revenue engine. I’ll do that for the rest of my life if I want to,” she says.

But her second venture is the one that excites her most.

It’s called The Growth Department. What started as a podcast and content series has grown into something bigger—a place to explore why companies get stuck, and why no amount of strategy helps if the leadership mindset stays the same.

“You can read every book on scaling. If your leaders can’t say, ‘I don’t know, let’s go find out,’ then none of it matters,” she says. “Culture starts at the top. Growth is personal.”

She’s launching the podcast this summer. The studio is painted moody blue. The first episode drops in June.

The One Thing That Gets Her to Her Desk Every Day

Chelsey blocks out 9 to 1 on her calendar each morning. The label just says “one thing.”

It’s inspired by the book Essentialism. It’s also a reminder.

“I cut everything back. Even clients. I just want to make space for what matters most right now,” she says.

And what matters most is figuring out what The Growth Department wants to become—and how to help founders build cultures where learning is valued as much as revenue.

“I’m not chasing scale. I’m chasing depth,” she says. “If that means doing fewer projects that matter more, I’m in.”

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