Chief Revenue Officer · B2B Technology · Cybersecurity · AI
CRO and GTM executive with 20+ years building data-driven revenue organizations. CISSP-certified. Former CTO. From $0 to $75M ARR across cybersecurity, AI platforms, enterprise SaaS, and technical services. I bring the technical credibility, AI fluency, and operational rigor that complex markets demand.
What I do
I've taken companies from zero revenue to $75M ARR and delivered $10M to $35M improvements at established organizations. This isn't incremental optimization. It's building the revenue architecture, hiring and coaching the team, then driving execution until the numbers compound. I design the GTM motion, align it across product, sales, and customer success, and lead the team through the hard middle of scaling. That includes international expansion into new markets. I've opened operations in China and the Middle East, and I've led GTM for both US-headquartered and foreign-owned companies including Swedish and Canadian organizations.
CISSP-certified, former CTO, and fluent in the language of CISOs, CTOs, and platform engineering teams. I sell to the buyers that generalist sales leaders struggle with, because I've been on their side of the table. In cybersecurity, AI, and enterprise SaaS, technical credibility isn't a nice-to-have. It's the difference between a 6-month sales cycle and a 14-month one.
I don't just sell AI products. I run GTM operations on AI infrastructure. Pipeline intelligence, agent-assisted execution, competitive analysis, meeting synthesis, forecasting. At Calliope AI, I built the GTM motion for a secure AI development platform while using AI tooling across every revenue function. This is how GTM teams will operate in two years. I operate this way now.
The hardest transition in B2B technology is moving from founder-led sales to a structured, repeatable GTM motion. I've done this multiple times: at Tehama ($0 to $27M ARR, category creation), at Broadwing (52% revenue growth and 32% ACV increase), and now at Calliope AI (10+ enterprise design partners, $140K ACV validated). I know what breaks during this transition and how to prevent it.
Revenue impact
| Company / Role | Type | Revenue | Key result |
|---|---|---|---|
| Calliope AI Founding CRO | AI Platform | $0 to first enterprise customers | 10+ design partners across cross-border commerce, healthcare technology, and global media. $140K ACV validated. 40% pilot conversion. |
| Equus Software Head of Global Sales | SaaS | $45M to $55M ARR | $10M new ARR. 22% ARR growth in 15 months. 15% ACV increase. 20% faster sales cycles. Clients included Bank of America, Deloitte, KPMG, 3M, IBM, Disney, and Toyota. Built team to 50 across 5 global offices with zero attrition. |
| Broadwing CRO | Services | 52% revenue growth, 32% ACV increase | Clients included HPE, Snap, Mizuho Securities, Google, and federal agencies. Built scalable data-driven sales organization. Launched AI/ML consulting offerings. |
| PKWARE VP Global Sales | Cybersecurity | $60M to $75M ARR | 50% faster sales cycles. 30% deal size increase. 91% forecast accuracy. Post-M&A integration of two technologies. Clients included Fiserv, JPMC, Visa, Wells Fargo, and United HealthCare. |
| Pythian VP Global Strategy and Sales | IT Services | $12M to $45M ARR | ASP from $5K to $45K (275% deal size growth). $6M in direct bookings as top sales leader. Counseled 20+ Fortune 500 clients. Built 5 new products. LTV:CAC 10:1. Acquired by Mill Point Capital (PE). |
| Tehama Co-founder, VP Global Strategy, Product and Sales | SaaS | $0 to $27M ARR | Enterprise SaaS category creation. ACV from $50K to $300K+ (145% increase). $50M valuation. 5-person team delivering what typically requires 30+. Clients included ARM, Upwork, Booking.com, and federal agencies. NDR 145%. Backed by OMERS Ventures and BDC Capital. |
| Apica VP Sales and COO North America | SaaS | $0 to $10M ARR in 18 months | 180% deal size increase. NDR 130%. LTV:CAC 8:1. Launched 3 GTM strategies. Channel: AWS, Rackspace, GCP, Azure. Swedish-founded. Backed by Industrifonden, Nordic Venture Capital, and SEB Foundation. |
Framework
Most revenue operations teams treat GTM models and revenue flow models as interchangeable. They're not. Your GTM model is a strategic choice: PLG, sales-led, hybrid, partner-led. Your revenue flow model is how that strategy actually operates: stages, conversion rates, velocity metrics, handoff logic, measurement.
SPORT5 codifies this distinction into five pillars that give RevOps teams a clear blueprint, so they're building infrastructure that matches how revenue actually flows through the business, not systems that wag the strategy around.
Read the deep dive →Selected work
Built the go-to-market foundation for an interview assurance platform: product positioning, ROI framework, investor pitch structure, and pre-launch competitive strategy in a nascent category.
AI PlatformDeveloped a six-part editorial calendar targeting every stakeholder in the enterprise buying process, from data scientists to CFOs, for a secure, multi-model AI development platform.
Revenue OperationsResearch-backed framework for sequencing GTM motion transitions, including comp model redesign, attribution systems, and cross-functional alignment for companies scaling from product-led to partner-led growth.
InteractiveLive ROI calculators, cost models, and strategic frameworks I've built for cybersecurity and AI companies. Functional tools, not slide decks.
What people say
"Craig is a very experienced and knowledgeable GTM leader. He successfully led a significant GTM change management project which was highly impactful on our business."
"He's a rare blend of sales superstar and technical wizard."
"Craig is my all-time favorite GTM partner. Their strategic insights and thorough understanding of market dynamics have been instrumental in successfully launching products that meet and exceed market needs."
Whether it's cybersecurity, AI, enterprise SaaS, or technical services: if the buyers are sophisticated, the product is complex, and the problem is worth solving, I'd welcome the conversation.
Get in touch