Empowering leaders to delegate. Elevating talent to thrive.

Trusty Oak is an award-winning fractional talent network that connects growth-oriented leaders with vetted US-based Executive Assistants, Specialists, and Fractional Executives.

As business owners ourselves, our experience, perspective, and values guide us in creating partnerships that feel supportive and meaningful for all. We're committed to cultivating a thriving and diverse community of clients, partners, and talent.

Helping clients take back 100k+ hours since 2016
Saving clients $6M+ through smart delegation
Partnering with 40+ vetted US-based professionals

Whatever the dream, Trusty Oak can help you make it a reality.

Our values

  • Build Trust

    Build trust: We build lasting relationships through transparency, reliability, fairness, and consistency.

  • Increase Quality

    Increase quality: We maintain the highest standards in everything we do, from client communication to talent recruitment.

  • Foster Collaboration

    Foster collaboration: We share knowledge and support each other, our talent, and our clients to make everyone better off.

  • Stay Flexible

    Stay flexible: We promote work practices that allow our team and talent to thrive professionally and personally.

  • Keep Growing

    Keep growing: We actively pursue personal and professional development, helping our team, talent, and clients reach their full potential.

Meet the core team

Zack Pennington, CEO & Co-Owner of Trusty Oak

Zack Pennington

CEO & Co-Owner

Jacy Cruz, COO & Co-Owner of Trusty Oak

Jacy Cruz

COO & Co-Owner

Bex Howell, Business Development Specialist at Trusty Oak

Bex Howell

Business Development Specialist

Corie Luzon, Client Success Manager at Trusty Oak

Corie Luzon

Client Success Manager

Lauren Lea Warren, Administrative Specialist at Trusty Oak

Lauren Lea Warren

Administrative Specialist

Our guarantee

At Trusty Oak, our core values are trust and respect. All Trusty Oak freelancers have gone through a careful and deliberate vetting process, ensuring they're not only highly skilled but also honest, committed, and professional.

  • Committed to Your Success

    Committed to Your Success

    We're committed to our clients' business growth.

  • Experienced Professionals

    Experienced Professionals

    We actively recruit the top freelancers in the U.S.

  • Trustworthy Support

    Trustworthy Support

    You'll never be ghosted by Trusty Oak talent.

The trusty oak guarantee

We're here to help

Our process is designed to create successful, rewarding partnerships. Book a call or send us a message to learn more about how it works.