An American company built on trust.

2015 Founded

Our roots

Trusty Oak was founded in Austin, Texas by Amber L. Gray, 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.

2025 Acquired

A new chapter

In March 2025, my wife Jacy and I (Zack Pennington) 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.

0 k+ hours returned to clients
$ 0 M+ saved through delegation
0 + U.S.-based professionals

Meet the core team

We keep our core team small, so we can stay flexible, efficient, and close to our clients and talent.

Zack Pennington

Zack
Pennington

CEO & Co-Owner

Jacy Cruz

Jacy
Cruz

COO & Co-Owner

Bex Howell

Bex
Howell

Business Development

Corie Luzon

Corie
Luzon

Client Success

Lauren Lea Warren

Lauren Lea
Warren

Admin Specialist

Our vision

We believe the future of work is flexible, technology-enabled, and built around trust.

Trusty Oak exists to make it easier for business owners to get the right support at the right time, without the friction, risk, or rigidity of traditional hiring. Not every need requires a full-time role, and the best results often come from matching expertise to the moment.

We embrace tools and technology, including AI, that help businesses move faster and operate more efficiently. At the same time, we believe there will always be work that benefits from human judgment, context, and reliable follow-through.

Our vision is to build the most trusted network of U.S.-based support professionals, equipped to work alongside modern tools and help businesses grow in sustainable ways.

Our core values

How we show up for our clients, our talent, and each other

Build trust

We earn trust through transparency, reliability, and consistency.

Increase quality

We hold high standards across everything we do.

Foster collaboration

Better outcomes come from shared knowledge and strong partnerships.

Stay flexible

We support work that adapts to real lives and real business needs.

Keep growing

We believe in continuous learning and development.

Ready to work with us?

Whether you need support or want to provide it, we'd love to connect.