The people behind it

We’ve run businesses too.
We know what’s on your plate.

We’re not here to sell you on AI. We’re here because we’ve felt the same overwhelm you have — and we found a way through it.

Groundwork started from a simple observation: the people running real businesses in Chattanooga — the salons, the boutiques, the studios, the practices — are working incredibly hard. They know AI could help. They just haven’t had the time, the right guide, or the right room.

We built Office Hours because we believe the best learning is specific, hands-on, and social. Not a course you watch alone. Not a consultant who hands you a report. A morning in a beautiful space with other business owners figuring it out together — and leaving with something that actually works.

We show up in person. We work on your actual problem. And we’re local — which means we’re here before the workshop, and we’re still here after.

What we believe

Specific beats generic, always.

A workflow built for your bakery’s invoicing is worth ten AI 101 courses. We never teach to a room — we solve for a person.

Community is part of the product.

The people you meet in the room are as valuable as what you build in it. Chattanooga is a small city. That’s a feature, not a limitation.

The day should feel worth taking.

Nice venue. Good breakfast. A morning you gave yourself. You’ve earned the space to invest in your business.

The founders

Co-founder

Jen Dennard

Jen is an operator’s operator. She co-founded and ran Range.co as COO, led strategy at Lake Partners, and has spent her career helping organizations figure out how to actually work — the systems, the people, the finances, the growth.

She brings that same rigor to Groundwork — not as a tech evangelist, but as someone who has lived inside the operational chaos of a growing business and knows exactly where AI can take something off your plate.

Operations Finance People Ops GTM

Co-founder

Megan Caldwell

Megan is a builder of organizations and communities. With a background in management consulting and human-centered design, she served as Executive Director of Health for America — building a tech-enabled health solution from scratch and successfully transitioning it to MedStar Health.

She’s spent her career asking “what do people actually need?” before building anything — and she brings that lens to every Office Hours workshop. The pre-consult is very much her influence.

Human-Centered Design Consulting Community Building

Ready to sort it out?

The pre-consult is free.
The conversation is easy.

Thirty minutes. We’ll talk through your business and figure out together if Office Hours is the right fit. No pressure, no pitch.

Book your consult →