This case tells the story of a small business’ succession plan journey in two parts. Closed Loop is a small insurance software company that is transitioning from a founder-run startup to manager-run company. Case A follows the 55-year-old founder Alex Martin as he performs a measured succession planning analysis that eventually leads him to promote from within the company. Neevan Chattry is the 33-year-old head of business development who has been with the company for ten years and shows promise as a rising leader. Over the course of 18 months, Alex and Neevan embark on a structured preparation and handover process. The case ends in June 2015 with Neevan taking over as CEO and Alex stepping into the role of board chairperson. Case B picks up two years later when Neevan unexpectedly announces that he is resigning as CEO, leaving Closed Loop in a difficult position. In this case, Alex confronts the mistakes he made over the last three years, both during succession planning and Neevan’s tenure as CEO, as well as how digital disruption in the insurance industry affected the business strategy over this period. The case ends with Alex resuming the role of CEO to lead Closed Loop in a reinvention process. Students are left to analyse the decisions taken by the different leaders and how Closed Loop will fair in the future under Alex’s leadership.