In Conversation: Two CLOs (Andy Cooke & Sam Ross) on Communication, Performance and Ethics

Alex and Tom step aside for this one—no hosts, no scripts—just Andy Cooke (CLO of Perk) and Sam Ross (CLO of Remote) in conversation. What begins with nursery vomiting bugs quickly evolves into a refreshingly honest exploration of what it means to lead a legal function in disruptive technology companies. They dissect the tension between being "bold, brief, and gone" versus staying in the room to build genuine relationships, challenge the limiting "trusted advisor" archetype, and wrestle with when precision matters less than context and authentic communication. Andy and Sam don't just theorise—they get personal about the moments that test you: deciding whether someone's lying on an expense claim, navigating board dynamics when you're the least financially fluent person in the room, and maintaining ethical standards when the stakes are existential. But this isn't a heavy-handed meditation on professional responsibility. The conversation crackles with levity and self-awareness - from Sam's admission that he deliberately uses humour to "pierce through" hierarchy, to their shared recognition that being fallible and human is part of doing the job right. Both find genuine joy in what they do, drawing energy from learning from others and building networks that pay dividends years later. It's a masterclass in thoughtful leadership wrapped in the warmth of two friends who clearly respect each other's craft - and aren't afraid to acknowledge when they get it wrong. If you enjoyed this episode, please like, subscribe, comment, and share! It gives us a warm fuzzy feeling and helps make our podcast more discoverable to other podcast aficionados!

For more thought-provoking conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/ for: (i) Focused conversations with leading practitioners, technologists, and educators; and (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis and visualisation of how AI is augmenting our potential.