An American company built on trust.

Our roots

Trusty Oak was founded in Austin, Texas by [Amber L. Gray](https://www.linkedin.com/in/amberlgray/), a visionary entrepreneur with a simple belief: everyone deserves meaningful, flexible work that fits their life. Amber built Trusty Oak to empower talented people who didn't fit the mold of a traditional workplace, giving them a place to do fulfilling work and support clients in a way that felt human, reliable, and collaborative. That spirit of empowerment shaped Trusty Oak's early years and continues to guide everything we do today.

A new chapter

In March 2025, my wife [Jacy](https://www.linkedin.com/in/jacycruz/) and I ([Zack Pennington](https://www.linkedin.com/in/zackpennington/)) stepped into ownership of Trusty Oak. After more than two years inside the business as COO, Jacy had seen firsthand the strength of the community Amber built and the opportunity to help it grow. I've started or been on the founding team of more than six companies across tech, hospitality, and services. I've spent my career building lean teams, launching new ventures, and helping founders scale without unnecessary complexity. That experience directly shapes how we support clients today. Jacy has spent over 15 years supporting founders and small business owners in customer experience and operations roles. She understands the realities of running a growing business with limited time, competing priorities, and constant demands. As a married team that has built multiple businesses together, we bring shared experience and complementary strengths to the way we lead. We know what it takes to balance vision, execution, and family life, and we understand the relief that comes from having the right support at the right moment. Stepping into Trusty Oak was not just a business decision for us. It was a continuation of a mission we deeply believe in.