Anthony Sottile is the VP of Partner Success at Freewill, a startup that enables free estate planning and has helped individuals commit more than $11B to charity. 

Anthony's direct reports describe him as down-to-earth and accessible, and emphasize his ability to lead through humor and celebration. 

In this episode, Annie Riley sits down with Anthony to discuss his insights on creating a transparent and honest workplace culture, celebrating team successes, and the importance of approachability in leadership. 

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Best Manager Ever shares the secrets of building and leading winning teams from the most successful and beloved leaders in the startup and tech worlds. All guests have been nominated as the “best manager ever” by their direct reports. Before each interview, we collect feedback and stories from their team about how the guest *actually* shows up as a leader. Each episode unpacks that feedback and explores the guest’s leadership playbook and lessons learned. Our goal is honest, actionable conversations that help you build your own leadership playbook and serve as an expert mentor and friend in your pocket. 

This season, we’ll continue delivering leadership lessons and management advice that you can apply immediately. We’ll go into more specific stories, and chat with leaders from new industries and functions, including Customer Support, People Ops, and Finance.

Season 2 drops March 26th, with new episodes every Wednesday.

Subscribe to make sure you never miss an episode, and join the conversation on Substack. 

Join us on Substack 

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Nominate your Best Manager Ever for the Podcast

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Amanda Richardson is the CEO of CoderPad, a technical interview and assessment platform. Amanda built her career in Product, and previously led the product teams and played a critical role in scaling the company at HotelTonight and Prezi. 

Amanda has built a reputation as a dynamic and direct leader. Her direct reports describe her as transparent, authentic, and someone who fosters trust and vulnerability within her teams.

In this final episode of season one (!), Annie Riley, Founder of Fort Light sits down with Amanda to dive into her leadership principles, discussing how Amanda builds and monitors team health, the importance of clear expectations, and how to take responsibility as a leader. Amanda emphasizes curiosity, direct communication, and the importance of diving into conflict head-on.  

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Namrata Ganatra, is the Chief Product and Technology Officer at Pipe. She has a notable career in tech and startups, including roles at Facebook, Coinbase, BloomTech Lambda School, PayPal, and Microsoft. 

Namrata's direct reports praise her for balancing technical expertise with empathetic leadership, and highlight her as a hardworking and inspiring leader with a strong focus on accountability and growth.

In this episode, Annie Riley, founder of Fort Light, sits down with Namrata to discuss her approach to quickly building trust within teams, her unique strategy for managing transitions during chaotic periods, and her method for balancing technical expertise with people management. Namrata also shares insights on fostering innovation and staying ahead of industry trends, providing valuable lessons for both startup leaders and aspiring managers.

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Nominate your Best Manager Ever for Season 2

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Mari Nazary is the CEO of App Academy, and brings a strong background working at the intersection of product, operations, and learning science at several ed tech companies across different stages. 

Her team praises her as the best leader they’ve ever had, citing her strengths in systems, process, and talent development. 

In this episode, Annie Riley, Founder of Fort Light dives into Mari’s unique approach to building trust and rapport quickly, and how she seamlessly blends high expectations with extensive support for her team. They also discuss frameworks for assessing team members’ competencies, the significance of feedback and tools in management, and maintaining personal relationships while navigating professional growth and performance challenges.

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Nominate your Best Manager Ever for Season 2

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In this special New Year's episode of Best Manager Ever, Founder of Fort Light, Annie Riley dives into self-management for leaders. Drawing from personal experience and past interviews with top managers, Annie shares insights on how to set yourself up for success in 2025. Key strategies include taking necessary breaks to avoid burnout, identifying daily activities that bring joy and recharge you, preparing for inevitable workplace chaos, and investing in healthy work relationships. This bonus episode offers invaluable advice for leaders aiming to thrive in their roles and foster a positive work environment this year.

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Nominate your Best Manager Ever for Season 2

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In this special holiday spoof episode of Best Manager Ever, Annie Riley, host and founder of Fort Light, chats with the one and only Santa Claus! Known for spreading holiday cheer and managing a diverse team at the North Pole, Santa gives a rare interview about life behind the scenes. His direct reports, including elves and reindeer, praise Santa for his leadership, though they note he's their only manager ever. 

We dive into Santa's leadership style, the secrets behind the naughty and nice lists, and the challenges of maintaining the Christmas spirit all year long. Join us for a fun-filled episode with laughter and insight into the man behind the magic.

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Nominate your Best Manager Ever for Season 2

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Alan D'Souza is the Director of Analytics at Credit Karma, and formerly led teams at Lending Club and Upgrade Inc. 

Known for fostering a culture of fun, hard work, and results, Alan's direct reports recall his empathetic and direct feedback style, along with his ability to inspire and motivate with humor. 

In this episode, Annie Riley, founder of Fort Light sits down with Alan to discuss his transition from startups to larger organizations, the distinction between managing small and large teams, and how he channels humor appropriately in different work contexts. He also shares his views on encouraging experimentation and innovation, the importance of transparency and radical accountability, and the necessity of maintaining a collaborative and engaging work environment to achieve team success.

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Nominate your Best Manager Ever for Season 2

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Sara Romero-Heaps is the Chief Product Officer at Seesaw Learning. She has built her career at the intersection of education and technology, and previously led product and content at Nearpod.

Sara is known for aligning her team's individual aspirations to business goals, and her direct reports describe her as a visionary and empathetic leader.

In this episode, Annie Riley, Founder of Fort Light, discusses with Sara the importance of discovering where employees want to grow and identifying how that aligns with the company's needs.

If you're looking to understand how to effectively foster growth in a way that benefits both individuals and organizations, this episode provides valuable perspectives and practical advice.

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Thianh Lu is the Chief Product Officer at Autograph and is a 3x founder, with one company acquired by WordPress and another by Blockchain.com.

He has a unique and well-rounded perspective on leadership, having been in the roles of early employee, later-stage executive, and founder/CEO. 

Thianh's direct reports praise his empowering and collaborative style, and remember him for building high-trust teams with a rapid tempo of learning and development. 

In this episode, Annie Riley, Founder of Fort Light  sits down with Thianh to discuss the importance of specific feedback, fostering a culture of learning, and balancing speed with thoughtful decision-making. Tune in to learn how Thianh's unique blend of curiosity and rigor drives both personal and team growth in dynamic startup environments.

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Nominate your Best Manager Ever for Season 2

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