Overwhelmed by life? Alison Stewart gets it—and she’s building a startup to help fix it.

In Part Two, the Overalls COO shares how her team is rethinking employee benefits by offering something surprisingly human: life support, literally. Whether it’s booking a plumber, navigating eldercare, or finding summer camps before the January rush, Overalls acts as a concierge for the chaos of modern life.

Alison also opens up about what it really takes to scale an idea from zero—while trusting yourself to write the policies, run the ops, and still answer the phones. Spoiler: she’s done it all. If you’ve ever dreamed of building something meaningful from scratch, this is your operations masterclass.

Key Highlights of Our Interview:

What Overalls Actually Does (Hint: It’s Not Laundry)

“We’re your life concierge—handling everything from vetting plumbers to eldercare planning. Our job is to give your time and sanity back.”

The Startup Test: From Strategy to Scheduling Cleaners

“Two weeks in, I was calling Colorado well inspectors, pitching insurance partners, and writing job descriptions. All in one day. That’s startup life.”

Why a Stay-at-Home Mom Might Be Your Next Concierge

“We tapped into an overlooked talent pool—retirees, caregivers, underemployed parents—and gave them flexible, meaningful work. It’s a win-win.”

HR Is Finally Getting Thank-You Notes

“Employers tell us: this is the first time employees are actively thanking HR for a benefit. That’s unheard of.”

The Burnout Solution That Isn’t Therapy

“Burnout isn’t always solved by meditation apps. Sometimes, it’s about having someone book that MRI or call the insurance company for you.”

Confidence as a Startup Operator: Earning It Day by Day

“Do I know how to write an HR policy? Not at first. But I figured it out. In a startup, everything’s your job.”

Why Big Company Life Doesn’t Prepare You for This

“In corporate, you focus on one slice. In startup life, you are the pie. You handle everything, whether or not you’ve done it before.”

From Lean to Leveraged: Hiring with Intention

“Writing job descriptions meant I could finally hire someone to take something off my plate. But no one else was going to write them.”

Mindset > Metrics (At Least in the Beginning)

“Don’t just optimize for titles or compensation. Start with: What am I actually excited to build? What problem do I care enough to solve?”

Advice for Fellow Change Progressives

“Talk to people. Write it down. Be honest about what lights you up—and patient with the timeline. Growth is a slow burn. Trust it.”

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Host: Vince Chan | Guests: Alison Stewart

--Chief Change Officer--
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