I’m a commercial and marketing leader who’s spent two decades building category-leading positions for data and AI powered enterprise solutions. My focus is on the challenging space where breakthrough technology meets enterprise adoption – translating complex capabilities into clear business value and sustainable growth.

Currently, I’m Chief Commercial Officer at CaptionHub, where I lead go-to-market strategy for our AI-powered multimedia localisation platform. We serve global enterprises including Amazon, Oracle, NVIDIA, and Stripe, helping them communicate with worldwide audiences at unprecedented speed and scale. I’m proud that we’ve built this from the ground up to an eight figure EV business with exceptional unit economics (1:12 CAC:LTV, 119% NRR) and achieved recognition as category leaders – including winning the 2024 Process Innovation Challenge Europe Award for our breakthrough live-subtitling technology.

Before CaptionHub, I held a SLT level roles for two VC/PE-backed enterprise SaaS companies, as VP Product Strategy (combining both CMO and CPO lead reporting to CEO and the board) and Head of Global Professional Services and led the businesses to successful acquisitions. I then founded Rise, a Forbes Top 10 Fitness App that pivoted to enterprise wellbeing. I’ve learned that the best marketing for transformative technology comes from genuine category creation, cross-functional alignment, and staying relentlessly focused on the problems that matter to customers.

My approach combines strategic thinking with pragmatic execution. I believe in building high-performance teams, using data to drive decisions, and maintaining the discipline that creates sustainable growth rather than vanity metrics. Whether it’s positioning a product, closing an enterprise deal, or scaling a partner ecosystem, I focus on work that builds long-term enterprise value.

I’m also a qualified executive coach (having trained under Carol Wilson and team, ex-Virgin Group MD with Richard Branson) and I mentor various founders, including for New Native’s AI accelerator navigating the unique challenges of scaling technical products into enterprise markets.

When I have time, I write and journal (badly) about go-to-market strategy, category positioning, and the intersection of AI, enterprise adoption, and market transformation at TL;DR Technology – my Substack covering the latest in AI and technology from a European perspective.

If something here resonates, I’d enjoy connecting. Find me on LinkedIn or reach out directly at james@jjameson.net.

What I’m thinking about lately:

• How enterprise AI companies can build sustainable competitive moats beyond model performance
• The intersection of product-led growth, enterprise sales, and education-led expansion—and why the companies that master all three will dominate their categories. Long-term genuine leadership and trust are the foundations that make PLG work at enterprise scale. I curate a list of top PLG leaders on X whose thinking influences how I approach this challenge, and maintain dealroom.vip – my personal collection of essential GTM resources and frameworks
• The gap between AI capabilities and enterprise readiness to deploy them
• Why the best B2B marketing in 2025 looks more like education than advertising
• How to position technical products for non-technical buyers without losing developer credibility

These are just some of the the daily challenges I navigate at CaptionHub as many others do at other companies, as well as the themes that drive my writing, mentoring, and GTM resource curation. If you’re working on similar problems, particularly at the intersection of AI, enterprise adoption, and go-to-market strategy, I’d genuinely enjoy comparing notes.