About

I've spent 20 years turning technical products into revenue, by building the teams, strategy, and systems to make it happen.

Craig W. Irwin

I'm a Chief Revenue Officer and GTM executive based between the San Francisco Bay Area and Topanga, California. CISSP-certified, former CTO, and a six-time GTM leader across cybersecurity, AI, enterprise SaaS, infrastructure, and technical services. I build and scale revenue organizations across 20+ countries, for both US-headquartered and foreign-owned companies, spanning publicly traded and privately held organizations.

Career arc

My path to revenue leadership started on the technical side. As CTO at Third Wave Technology Services, I served as acting CTO and CIO for enterprise clients across financial services, media, and e-commerce, managing multi-million dollar technology transformation initiatives. That technical foundation taught me how products actually work, and why most sales teams struggle to sell them.

At Apica, a Swedish-founded application performance platform backed by Industrifonden, Nordic Venture Capital, and SEB Foundation, I built the North American business unit from zero as VP Sales and COO. It became the top revenue-producing region within 18 months, serving clients including the NFL and Activision.

At Pythian, I joined through the acquisition of Blackbird.io and grew the digital transformation practice from $0 to $45M, counseling 20+ Fortune 500 clients on data infrastructure, AI/ML, and cloud transformation. Pythian was later acquired by Mill Point Capital.

At Tehama, which I co-founded, I built the GTM motion from scratch for a secure remote access platform. $0 to $27M ARR, ACV from $50K to $300K+, with a 5-person team delivering what typically requires 30 or more reps. Clients included ARM, Upwork, Booking.com, and federal agencies. Backed by OMERS Ventures and BDC Capital. Canadian headquartered.

At PKWARE, I led global sales for the PK Protect data security suite. $60M to $75M ARR with 50% faster sales cycles, 30% larger deals, and 91% forecast accuracy. I led post-acquisition integration of two technologies and served clients including Fiserv, JPMC, Visa, Wells Fargo, and United HealthCare.

At Equus Software, I led global sales from $45M to $55M ARR, built a team of 50 across five offices in the US, UK, Portugal, and Philippines with zero attrition. Clients included Bank of America, Deloitte, KPMG, 3M, IBM, Disney, and Toyota.

Now at Calliope AI, I'm the founding CRO for a secure AI development platform. We've secured 10+ enterprise design partners, validated a $140K ACV model, and achieved 40% conversion from design partner to paid pilot.

The thread through all of it: I take complex technical products and build the revenue organizations that make them commercially successful. With 2x better capital efficiency than industry benchmarks.

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. The SPORT5 revenue operations framework came from seeing too many companies build tech stacks that didn't match how revenue actually flowed through their business.

But frameworks are only as good as the execution behind them. The biggest shift I see in GTM today isn't AI products. It's AI-powered execution. The companies that win won't just build better products. They'll build better systems to bring them to market.

Product-market fit is dynamic. It requires continuous feedback loops between customers and GTM teams, not a one-time exercise. And capital efficiency is a competitive advantage. The best companies scale smarter, not just faster. I bring this mindset to every revenue organization I lead.

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.