Josh Holmes, LEED AP

Commander
DISC Type : D

Founder at The CRO Toolkit

West Chester, Pennsylvania, United States

Overview

Josh Holmes is a Chief Revenue Officer specializing in scaling security, SaaS, and IT service companies. He builds high-performance revenue engines by aligning GTM strategy with modern revenue operations. He holds a Bachelor of Architecture from Philadelphia University and is a LEED Accredited Professional.

Based on past projects, Josh has a strong creative side with demonstrated interests in architectural design, art, and photography. He also appears to have hands-on experience with real estate renovation and investment, having maintained a portfolio of property flips.

Unique fact: This CROs academic background is in architecture, where he conducted research on aesthetic categories like "the picturesque" in fabrication.

Personality Overview

Very Quick

Impact-Driven

Candid & Clear

They are not focused on building rapport and relationships.  More than the product, they care about the effectiveness of the product. They respond better to strong and respectful interactions.

Topics They Care About

Fractional Leadership
He founded The CRO Toolkit, a peer community for fractional sales leaders, and frequently posts about the growing fractional executive market.
Modern GTM Models
His focus is on modernizing go-to-market frameworks to create predictable, scalable growth for PE-backed and technology companies.
Converged Security
At Harris Technology Services, he leads the strategy for integrating physical and digital security solutions for clients in various industries.

Media Appearances

Josh has no verified media appearances

Work History

1-2026
Founder at The CRO Toolkit
4-2022 - 12-2023
Fractional CRO at ALTA Language Services, Inc.
2-2022 - 5-2024
Sales Leader at The Sales Collective
1-2022 - 3-2026
Chief Revenue Officer (CRO) at Harris Technology Services
1-2020 - 2-2022
President, Future Workplace Consulting at Workplace Logix

Education

Education details unavailable from Thomas Jefferson University
Bachelor of Architecture (B.Arch.) from Philadelphia University

More Information

Social Presence :

Prographics :

Exp : 16 Location : West Chester, Pennsylvania, United States Job Level : Leadership Designation : Founder at The CRO Toolkit
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Insights For Selling To Josh

During A Call Or A Meeting

DO's

  • Hold your ground without indulging in one-upmanship
  • Be respectful but crisp
  • Make sure that you circle back fast on any action items, it wins their trust

DONT's

  • Avoid being too verbose
  • Do not spend too much time focusing on product tech or features
  • Do not back off when challenged, respond with a confident, objective answer instead

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Josh is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Josh

  • If they decide not to use your product, they will say no clearly.

Insights For Deal Planning

    How fast (or slow) will Josh move?

  • They can take decisions very fast if you manage to convince them.
  • Can Josh take some risk or not?

  • The risks don’t matter much to them.

You And Josh

Personality Compatibility


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