Ep 11: Craig Jackson (Director of Customer Success at Pleo)

    June 24, 2025
    Watch on YouTube

    About this episode

    In this episode, Craig shares his journey from early career roles in sales and recruitment to becoming a director of customer success in a hyper-growth FinTech company Pleo. He discusses the evolution of customer success functions, the challenges of scaling operations, and the importance of mentorship and team alignment. Craig also delves into what it takes to be an effective leader and offers advice for aspiring leaders in the field. 00:00 Welcome and Introduction 01:19 Craig's Early Career Journey 02:45 Joining a FinTech Startup 03:52 Scaling and Hypergrowth 09:29 Transition to Pleo 11:08 Building a Customer Success Team 24:10 Leadership and Mentorship 30:17 Advice for Aspiring Leaders 35:27 Final Thoughts and Outro GTM Leader Stories is powered by www.stackd.so