What does it take to execute a fundamental business pivot under intense pressure? Bob Segert, Chairman and CEO of athenahealth, shares the story of how he reset the company’s strategic direction after a merger and a take-private transaction. He reveals how he gained the conviction to go all-in on high-growth ambulatory care, his approach to change management, how he earned employee trust, and the operating mechanisms he implemented to drive organizational alignment.

• (00:00) - Intro
• (00:51) - Welcome Bob
• (01:43) - Upon joining athenahealth as CEO, what was the state of the company and your top priority initially?
• (03:12) - What prompted you to reset the company’s focus so early on in your role?
• (05:29) - What were the sources of data that allowed you to feel confident in deciding to focus on ambulatory care?
• (06:30) - What was your approach to change management to get buy-in?
• (09:17) - What advice can you share with leaders thinking about long-term planning?
• (11:34) - How have you seen the transition play out in the last six years?
• (14:20) - What is the most valuable principle or operating rhythm you've developed to make the right decisions?
• (16:31) - Thanks & Outro

What does it take to create lasting financial change? Kim Castro, recently retired Financial Transformation Leader with experience at Gap and CVS Health, shares how she fostered a more efficient and impactful financial organization at both companies. She explains how to set the strategic tone for a transformation, navigate change management within reluctant financial teams, bring key stakeholders in and develop a culture that leans into one another’s unique work styles.

• (00:00) - Intro
• (00:51) - Welcome Kim
• (01:19) - What does financial transformation mean?
• (02:05) - What circumstances drove Gap’s need for financial transformation, and what indicated they were ready?
• (03:04) - What was the first decision you made to establish a strategic tone for success?
• (04:10) - How did your experience at CVS Health differ from Gap, and what did you learn?
• (05:51) - What KPIs signal that transformation is working?
• (08:29) - What was the most impactful tactic you used to get buy-in for change management?
• (10:50) - How did you know the time was right to retire?
• (12:49) - What is the most powerful lesson you’ve learned about decision making during intense moments?
• (14:53) - Thanks & Outro

What does it take to turn a company around? Tony Stubblebine, CEO of Medium, shares how he brought Medium from the brink of financial collapse into the innovative, successful content platform it is today. He reveals how he balanced cost-cutting with the need for innovation, the importance of a strong moral compass in leadership, and how to rally a team when confidence is low. This episode is packed with actionable insights for any leader facing a high-stakes financial or morale challenge.

• (00:00) - Intro
• (00:51) - Welcome Tony
• (01:26) - Can you tell us about the company Medium?
• (02:12) - How did you navigate the first few months as CEO?
• (04:20) - How did your decision to do a single reduction in force impact the culture?
• (06:12) - How has your strong moral compass affected your leadership style and what principles guide you through difficult decisions?
• (08:40) - What financial decisions did you make to course correct Medium’s debt?
• (10:33) - What is Medium’s “Boost” feature and how was its launch critical to the turnaround?
• (12:13) - What lesson would you share with other leaders?
• (13:32) - Thanks & Outro