Benn Crawford

Most recently I was Chief Product Officer and General Manager at Totara Learning Solutions — a global SaaS company with over 200 staff, 1,500+ customers, and 20 million users across 147 countries. I rebuilt the product and R&D function from scratch, helped grow ARR by more than 3x over four years, and played a key role in a successful private equity transaction. Before that I led product at Silverstripe, including delivery of the NZ Government's Common Web Platform.

The pattern across my career is the same: I come in when a business has outgrown its founding operating model but hasn't yet built what replaces it. That means standing up product strategy, R&D structure, pricing, and go-to-market alignment — usually all at once, usually with constraints. I've done this across government, enterprise, and mid-market segments in EMEA, APAC, and North America.

I also build software with frontier AI tools. Not as a side project — as a real practice. I work daily with Claude, Cursor, and modern stacks. For a fractional engagement, that means I can evaluate your product technology strategy, talk directly to your engineers, and tell you whether an AI strategy is real or just a slide deck.

• Fractional CPO / Head of Product — strategy, roadmap, R&D operating model
• General management and P&L leadership for scaling SaaS companies
• AI and GenAI strategy — from board positioning to shipped product
• Product-led growth, pricing, and packaging for B2B SaaS
• Org design and high-performance team building
• Technical due diligence and PE/investor transaction support