About

The short version: I build revenue engines that compound, then I teach them to run themselves.

Craig W. Irwin

I'm a six-time revenue leader at the intersection of AI and cybersecurity, splitting time between the San Francisco Bay Area and Los Angeles. My track record is concentrated in the $10M to $75M ARR scaling band: the phase where Series B/C companies convert founder-led momentum into a repeatable commercial motion. I'm a CISSP-certified former CTO, which gives me peer-level credibility with the technical buyers who typically stall enterprise deals for other revenue leaders.

What I've built

Over the last 20 months, I've built what may be the most sophisticated AI-native BDR framework running in Series B/C SaaS today. A proprietary multi-agent system on Claude API, integrated with Clay, Apollo, Perplexity, Gong, Clari, and 6sense. Seven custom agents cover the full top-of-funnel motion: account discovery and enrichment, ICP-driven qualification and scoring, contact research and persona mapping, personalized outreach and sequence drafting, signal monitoring, industry scanning, and champion tracking. The result: a 3-person commercial team runs an enterprise motion typically requiring 12+ headcount. This isn't tooling adoption. It's system architecture.

Before that, I scaled Equus Software from $45M to $55M ARR in 15 months with a 50-person global team and zero regrettable attrition, completing the growth mandate I was hired to deliver. At PKWARE I grew ARR from $60M to $75M through a post-acquisition GTM integration, transitioning out upon mandate completion. At Tehama I took the company from $0 to $27M ARR over five years with a 5-person team delivering what typically required 30 reps. I've closed $200K to $2M+ deals with Google, Microsoft, Disney, Wells Fargo, Visa, HPE, Bank of America, Deloitte, KPMG, 3M, IBM, and federal agencies.

The pattern across all of it: I architect the commercial motion from first principles, recruit and coach the team that runs it, and build the systems that let lean teams outperform their headcount-per-dollar ratios.

Credentials

CISSP (Certified Information Systems Security Professional, #105332). ISSA member. Infragard member. Active in go-to-market and cybersecurity industry communities. Bilingual: English (native) and Spanish (professional working). Bachelor's degree in International Business and Spanish from the University of North Carolina Wilmington.

How I engage

Beyond my current role, I advise founders navigating the transition from founder-led sales to structured GTM, and occasionally take on focused 30 to 90 day GTM acceleration engagements: diagnosing growth bottlenecks, implementing scalable systems, and aligning product and revenue teams. I'm always open to conversations with leaders building in B2B technology, whether that's cybersecurity, AI, enterprise SaaS, or technical services.

How I think

I think in frameworks and systems. SPORT5 came from seeing too many companies build tech stacks that didn't match how revenue actually flowed through their business. I believe the distinction between a GTM model (a strategic choice) and a revenue flow model (an operational system) is one of the most under-discussed ideas in revenue operations, and getting it wrong costs companies years. The same architectural instinct drove the multi-agent BDR framework: most GTM leaders treat AI as a tool you buy; I treat it as a system you design.

Outside work

Craig W. Irwin competing in an adventure race

Competitor

Craig W. Irwin at the Zuma Beach Triathlon finish line

Coach

Craig W. Irwin and the Community Brigade wildland fire team

Community leader

I'm a competitive adventure racer, mountain biker, and triathlete. I met my wife competing in an Eco-Challenge expedition race in the Fijian jungle. The same discipline that gets you through a multi-day endurance race is what it takes to build a revenue org from zero: sustained effort, smart pacing, and no shortcuts. Today I coach and support my three daughters through cross country, track and field, triathlon, and mountain bike racing.

After the Palisades fire threatened our Topanga community, I completed wildland fire training and co-founded what became the Community Brigade, a structured community emergency response organization with LA County support. Leadership isn't something you turn off when you leave the office.