John Dillard

John Dillard

Co-Founder @ StealthCRX, Sign In Solutions, ThreatSwitch, Big Sky Associates
5.0
(4 reviews)
2-Time Exited Founder, SaaS Operator, No-BS Business Coach
United States of America Active this month

Services

$460 / month

Start free, decide later

  1. 1 Free 7-day trial
    No charge until day 7. Cancel anytime.
  2. 2 Ongoing calls + chat
    Regular 60-min calls plus unlimited Q&A via chat. Replies in 24 hours or less.
  3. 3 No lock-in
    Month to month, no contract.
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MentorCruise summary

John is a Co-Founder at StealthCRX and a two-time exited founder. He previously co-founded ThreatSwitch and Big Sky Associates, and he served as General Manager for Enterprise at Sign In Solutions. He helps founders build repeatable habits for growth, address early-stage business challenges, and strengthen leadership decisions.

Based on 3 verified mentee reviews

  • Reviewers often praise his practical experience building companies, including early-stage challenges and moving from consulting to a SaaS product.
  • Two reviewers value his thoughtful, tailored advice for specific business and leadership challenges.

About

I’m a 2-time exited founder and seasoned executive with deep experience in SaaS, Angel & Seed Funding, operations, continuous improvement, leadership, and management. I specialize in coaching early-stage companies, helping them establish repeatable habits for scale, and I actively invest in startups with high-growth potential. Most importantly, I don’t take on mentees or companies I can’t help—and I won’t BS you.

Previously, I was General Manager for Enterprise and part of the C-Team at Sign In Solutions, the company that acquired my most recent startup, ThreatSwitch. While I left my full-time role there in March 2024, I continue to serve as an advisor.

I’m also a volunteer Coach in Entrepreneurs' Organization’s (EO) Accelerator program, helping emerging companies break the $1M revenue barrier. As a Strategy Summit facilitator for EO, I work with leaders across the globe to strengthen their entrepreneurial ecosystems.

Before ThreatSwitch, I co-founded, grew, and sold Big Sky Associates, a consulting firm that helped companies and national security organizations deploy technology-supported continuous improvement.

What mentees say

5 out of 5 stars

John is an excellent mentor and an invaluable wealth of experience. As a twice-exited founder, he can assist companies with the unknown-unknowns, and help navigate the challenges early stage companies face. He can advise on a broad range of topics since he has had to face them in the companies he built and led. We have really benefited from his timely and well-thought through advice and can highly recommend him.

Kristen

Kristen

Standard Plan • 2 months

5 out of 5 stars

I was looking for a mentor with a rich background and some steps ahead of me who could share the lessons learned and contribute to my leadership challenges, and I found John a great match. He is attentive and full of tools and insights to share in every theme I have to deal with. The way he began the mentorship sessions was a great way to kick-off and talk about my challenges.

Gustavo

Gustavo

Standard Plan • 2 months

Gustavo wrote 1 more review for the same mentorship

5 out of 5 stars

Gustavo

Gustavo

5 out of 5 stars

John is the perfect mix of visionary CEO and practical integrator. I choose him based on his experience creating and converting a consulting business to a successful SaaS product. His advice was thoughtful and tailored to address my specific challenges. I would highly recommend John.

Adam

Adam

Session: Ask Me Anything - 60 …

What happens when you start

You tell John your goals. They see exactly what you want to work on before session one.

You meet within days. John reviews your application and books your first session, usually within a day or two.

You leave with a plan. Concrete next steps and a weekly rhythm from your very first week.

Start your mentorship