In this episode of the OSL Podcast, Rob sits down with Nick Sales to unpack what a fractional CTO actually does, how outcome driven retainers work, and why strong product, team, and technical foundations matter for growth stage companies. Nick also shares his non linear journey into consulting and startup advisory, plus his perspective on GenAI, where it shines for prototyping and where it can become risky in production if you do not yet know what good looks like.

This week, Rob sits down with Lucy Woodhead, VP of Operations at US Jetting, to talk about what it really takes to run and modernise a second-generation industrial business. From bringing specialist equipment online to improving internal operations, Lucy shares how a traditionally offline industry is adapting to new technology and what the future could look like for manufacturers like hers.

AI agents were hyped to be 2025’s big productivity breakthrough, but the real wins came from small, practical automations rather than bold “digital worker” fantasies. Businesses that focused on clear use cases, team upskilling, and quick, measurable improvements saw the most value, while grand AI transformations mostly stumbled due to messy processes and poor data.

In this episode of the OSL Podcast, Rob chats with creative powerhouse Evan Larbi about navigating a career that doesn’t fit neatly on LinkedIn. Their conversation covers everything from career pivots and purpose to the unexpected role of joy in building meaningful brands.

Ben Burch (Allegr) on non-linear careers, real community vs fake “social,” military service, and building mission-led tech without boiling the ocean. Hosted by Rob Woodhead

Real stories from the people building tech, founders, designers, consultants & creators. Honest convos. No fluff. Just the human side of innovation.