Explore every episode of the podcast Right Decisions, Right Now

Current conversations are all about job displacement, but what we should be paying attention to is skills displacement. In this episode, Coursera SVP and President of Enterprise Anthony Salcito joins host Jim Freeze to talk about preparing people for a workforce being reshaped by AI. The conversation explores why successful AI transformation starts with people rather than technology, how leaders can build employee buy-in instead of fear, and why a willingness to keep learning may be the most valuable skill in an era of constant change.

Government isn’t slow to adopt new technology because it’s resistant to change. It’s cautious because the stakes of getting it wrong are much higher than in other industries. In this episode, OpenGov Chief Product Officer Adam Rykowski joins host Jim Freeze to talk about bringing AI into the public sector, where trust and accountability are non-negotiable. The conversation explores how AI can give public servants more capacity, why government could set the standard for responsible AI adoption, and why the biggest risk for leaders may be inaction.

In aviation, everything from fuel prices to world events can change the plan overnight. Dave Harvey has spent his career making decisions in that uncertainty. In this episode, the longtime Southwest Airlines executive and former Chief Commercial Officer at Wheels Up joins host Jim Freeze to talk about what it takes to make a decision without perfect information: knowing your options, committing when the time is right, and staying ready to adapt as conditions change. 

Every 13 minutes, someone in the US dies in a road accident. By the end of today, 130 families will get a phone call that changes their lives forever. Johan Land knows that feeling firsthand. In this episode, Samsara's Chief Product Officer joins host Jim Freeze to talk about one of the most consequential product decisions a leader can face: whether to bring AI agents into an environment where getting it wrong isn't an option. 

Right Decisions, Right Now is a podcast about the decisions that define a leader’s career, and how leaders make them when the path forward isn’t obvious.

In Season 2, Anaplan CMO Jim Freeze sits down with leaders from companies including Samsara, Cardinal Health, Coursera, OpenGov, and more to unpack the moments that demanded a decision – what leaders knew, what they didn’t, how they moved forward anyway, and how AI is changing the speed and expectations of decision-making.

Tune in to hear candid stories about leading through uncertainty, acting with conviction, adapting when the facts change, and knowing when “I don’t know” means it’s time to go find the answer.

Follow Right Decisions, Right Now wherever you listen to podcasts. Season 2 premieres September 17.

For more information, visit anaplan.com/podcast.

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

What does it take to launch a new business inside one of the world’s largest financial institutions? Vineeth Subramanyam, Managing Director, Global Head of Spring by Citi, shares the story behind creating and scaling Spring, a platform designed to unlock enterprise value for Citi’s customers. He explains how the team identified the opportunity, overcame the challenges of innovating within a global bank, and built a business that balances customer needs with Citi’s scale.

• (00:00) - Intro
• (00:51) - Welcome Vineeth
• (01:24) - What is Spring by Citi?
• (02:00) - What is the story behind the name Spring?
• (02:40) - What were the hurdles for getting initiative buy-in, and how were they overcome?
• (04:04) - What success metrics and key financial indicators show enhanced enterprise value?
• (05:51) - How did you know tough decisions were paying off?
• (08:49) - What do enterprise leaders expect from a new payments provider, and how will it shift?
• (10:58) - What advice would you give your past self regarding making tough decisions?
• (14:52) - Thanks & Outro

What does it take to rebuild a brand and bring it into the mainstream? Amy Taylor, CEO of Zevia, shares how she joined the company at a pivotal moment and led its transformation into a household name. Drawing on lessons from her time as Red Bull’s CMO, including the high-stakes Stratos Project, Taylor reveals how she identified what was holding Zevia back and charted a bold new course for growth.

• (00:00) - Intro
• (00:51) - Welcome Amy
• (01:32) - What were your top priorities when you took over at Zevia?
• (04:14) - What ways of thinking consistently help you make tough calls?
• (06:08) - How do you make sure your decisions align with your financial objectives?
• (08:13) - What pivotal decisions did you have to make as part of the Red Bull Stratos team?
• (11:44) - How has your approach to making high stakes decisions changed?
• (13:53) - Thanks & Outro

Right Decisions, Right Now is a podcast where we explore the choices that define a leader’s career. In each episode, Anaplan’s CMO, Jim Freeze, sits down with executives from various industries to unpack pivotal decisions — bold breakthroughs, tough calls under pressure, and the moments that shaped their careers and companies. 

Tune in to get inspired by the stories of today’s leaders and the pivotal moments that shaped their success. 

For more information, visit anaplan.com/podcast.