Passionate about product, people and making things happen

I’m a natural problem-solver, endlessly curious, and (warning!) I ask a lot of questions.

I co-founded a $25M channel incentive software business, which employed 60 people and sold in 2020, so I know first-hand what it takes to start, grow, and scale a successful company. I’ve played every role, navigated the growing pains, and had to learn how to adapt quickly while keeping the bigger picture in focus.

Over my 25+ years in product leadership, I’ve coached teams, defined strategy, managed the full product lifecycle, and led GTM launches. I’m not just a “deck and post-it” strategist. I’ve been hands on - shaping ideas, validating problems, building products, and shipping them into the world. And honestly, I still love getting stuck into the detail.

The Strategy Sessions is the best of everything I’ve learned about product, facilitation & collaboration. Most of my projects begin with a workshop — give me a magic whiteboard and a stack of sticky notes and I’m in my happy place. I design sessions that take teams on a journey: uncovering problems, sparking ideas, building alignment, and turning talk into action.

Hi, I’m Jules - founder of the Strategy Sessions

Jules Caswell Strategy Sessions Product Workshops

Why work with me?

  • Exited co-founder of a $25M channel incentive software business (60 employees, global clients)

  • 25+ years of product leadership experience across SaaS, incentives & rewards, e-commerce, and ad tech

  • Hands-on track record of growing businesses, operational excellence and driving product strategy

  • Certified in ToP: Group Facilitation Methods — trained in leading workshops for team building, strategy, visioning, and consensus

  • And above all because I love working with passionate people, embedding myself in their team, and diving headfirst into their toughest problems!

I can help you with

  • Line drawing of a signpost with two directional signs attached to a post.

    Fractional Product Support

    Need product leadership without hiring a full-time CPO? I bring senior expertise to help you set direction, fix processes, and accelerate growth — on a flexible, part-time basis.

    Fractional Support
  • Red outline of a four-piece jigsaw puzzle

    Strategic Sessions

    Struggling to step out of the day-to-day? I design and facilitate thought provoking workshops that take you and your team on a collaborative journey of exploration, decision making and action planning.

    Strategic Sessions
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    2-hour Workshops

    Fast, focused, fun sessions on topics like prioritisation, collaboration, and change management. 2 hour interactive workshops are designed to energise teams, build skills, and spark lasting change.

    Workshops