Simon Kaastrup-Olsen
Commercial strategy · Product · AI implementation · Go-to-market

Simon is the commercial and product entry point of the practice. He has operated as Chief Product Officer (CPO), Chief Strategy Officer (CSO), and Chief Executive Officer (CEO) across startups, scale-ups, and a legacy turnaround — and is the practitioner most clients meet first.
The career has run on both sides of the table. Founded and led companies — including productising data science into a business-to-business (B2B) software-as-a-service (SaaS) that beat a 4.2Bn USD competitor for an Asian partnership, and a business-to-consumer (B2C) artificial intelligence (AI) product in esports that reached acquisition talks with the largest US esports organisation in the field. Inside scale-ups, led the rebuild of a Data Science offering at a pharmaceutical consultancy. Defined the technical consultancy at Ciklum, scaling it from 20 to 220+ specialists — the foundation for what is today a 4,000+ person business. At a Nordic pharma-client, defended several million euros of strategic cloud investment to executive management and a board comprised of senior Danish life-sciences executives.
Currently sits on two commercial real estate company boards. Working stack runs in open source and modern AI tooling — retrieval-augmented generation, agentic workflows, fine-tuning, and the surrounding data infrastructure — alongside product engineering across Next.js, .NET, and Python. Maintains specialist networks across regions the practice draws on when an engagement needs to scale specialist capacity at speed.
Strongest in
Turning strategic ambiguity into actionable direction; AI implementations anchored in business strategy; getting leadership aligned on what they actually want to build.

