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Best Manager Ever
Best Manager Ever: Darius Contractor - Leading Through Frameworks and Analogies
Darius Contractor is the Chief Growth Officer at Otter AI. Darius has had a long and impactful career in the startup and tech worlds. Prior to Otter AI, he led engineering, growth and product teams at Vendr, Airtable, Facebook, Dropbox, Bebo and more. He is also an investor and advisor in multiple companies and funds.
Darius’s direct reports describe him as a master of frameworks and analogies, someone who balances detail orientation with a big-picture vision, and a manager who pushes boundaries with unconventional but memorable approaches.
In this episode, show creator and Fort Light founder Annie Riley sits down with Darius,
and they discuss:
- How to support your team’s career path in a fast-paced, high-growth environment
- The SEEN framework for career development
- Designing jobs like dinner plates
- How frameworks and analogies make concepts more memorable
If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.com
Check out Fort Light to level up your leadership skills
Connect with our show’s Producer, Alexis Ramdaou
Nominate your Best Manager Ever for the Podcast
This is a Production of Fort Light and Now it’s Hear
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15. Best Manager Ever: Santa
13:19||Season 3, Ep. 15In 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 will 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.Connect with Annie RileyConnect with our hilarious Santa, Jason GoreListen to Jason’s podcast 108.9 The HawkCheck out Fort Light to level up your leadership skillsConnect with our show’s producer Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear
15. Best Manager Ever: Top Takeaways From Season 3
20:24||Season 3, Ep. 15In this recap episode of Best Manager Ever, host Annie Riley reflects on standout lessons from Season 3.Annie discusses the six things our top manager guests have in common: high standards, clear communication, strong relationships with peers, a relentless focus on their own growth, a unique view of career management, and a human-first perspective. It’s a chance to pause, look back, and notice what makes our guests so exceptional— and then think about how to apply those lessons in your own work. Whether you're a longtime listener or just tuning in, this episode offers a meaningful recap of the themes that shaped our season. Share your feedback and suggestions from the season in this super quick form, so we can make future episodes even better. If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear
14. Best Manager Ever: Jared Erondu – Hard Mode Leadership
52:09||Season 3, Ep. 14Jared Erondu is a seasoned design and startup leader, and is currently the Head of Design at early-stage startup Span. Jared spent eight years at Lattice rising from a solo designer pulling all-nighters in the early days, to leading a 50-person design organization and serving as GM across product and GTM as the company scaled. Earlier in his career, he was a design leader at Teespring and Omada Health. Jared is known for his design mentorship and community-building, and is an active advisor and angel investor. Jared brings a calm, steady presence, especially during challenging times, always seeing the long view and providing unwavering support. His team appreciates his high standards, attention to detail, and commitment to craft, but also noted that he balances intensity with humor and approachability.In this episode, show creator and Fort Light founder Annie Riley sits down with Jared, and they discuss:Why all managers should master selective transparencyThe right way to communicate destabilizing intel How to recondition your mindset for “hard mode” leadershipHow to build a bench of resources to support yourself The best way to recruit exceptional talent Why managing your own mindset is the ultimate leadership unlock If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Jared EronduConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear
13. Best Manager Ever: Dana Lawson - Conquering Imposter Syndrome and Fostering Team Resilience
43:35||Season 3, Ep. 13Dana Lawson is the CTO of Netlify. She’s been a technologist for decades, and was previously the VP of Engineering at Github and the Director of Engineering at New Relic, Heptio, InVision (acquired by Miro), and more. Dana has a diverse background, and served in the military. Dana's direct reports praise her for building confidence, providing autonomy support, for bringing honesty and compassion, and for sponsorship that goes beyond mentorship. In this episode, show creator and Fort Light founder Annie Riley sits down with Dana, and they discuss:How imposter shows up at senior levels– and how to handle it How to deal with interpersonal conflictsWhat it takes to be an effective sponsorThe importance of embracing changeIf you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Dana LawsonConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear
12. Best Manager Ever: Amit Shah - Building Trust Through Gratitude
48:46||Season 3, Ep. 12Amit Shah is the COO of Virta Health, where he’s built the company from ~30 team members to over 800 colleagues working to reverse obesity and diabetes. Amit has 10+ years of experience in building and scaling entrepreneurial and high-growth healthcare organizations, with a focus on delivering financial and operational results while aligning on mission and values.Amit’s direct reports praise his ability to balance the needs of Virta’s members, business, and staff, describing him as incredibly kind, caring, driven, and a fierce protector of his team. He is celebrated for his passion, structured thinking, dedication to his own growth and development, and continuous improvement in leadership.In this episode, show creator and Fort Light founder Annie Riley sits down with Amit,and they cover:How to build a gratitude practice that supports your team – and yourselfThe importance of emotional awareness and regulation in leadership Energy management habits and practices A process to take charge of feedback, learning, and growth The relationship between execution and strategy in startups If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Amit Shah Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s producer Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear
11. Best Manager Ever: Patrick Reynolds - Creating the Conditions for Success
39:44||Season 3, Ep. 11Patrick Reynolds is the Co-Founder and Head of Product at Office Hours, an expert marketplace. Patrick started his career as a software engineer, before becoming a self-taught product designer and making the leap into product leadership. He has worked at an array of tech companies and startups including Affirm, Sweep, and Adobe. Patrick's direct reports praise him for his exceptional thoughtfulness, noting his ability to remember personal details and small, meaningful actions that remove friction and boost morale. They describe him as a natural coach who not only sets high standards but also provides the necessary support and resources to achieve them. In this episode, show creator and Fort Light founder Annie Riley sits down with Patrick, and they discuss:The difference between leadership and management How to prime yourself so it’s easy to spot opportunities to support your team The difference between a culture that inspires ambition vs. enforces it How to consume content for maximum ROI The best way to spot (and stop!) perfectionism If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Patrick ReynoldsConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear
10. Best Manager Ever: Sophie Ruddock – Showing Up for Your Team During Crisis
40:12||Season 3, Ep. 10Sophie Ruddock brings deep expertise in scaling mission-driven tech companies, and is now the COO at Empathy. Sophie was an early employee at Multiverse, where she grew with the company and ultimately became their global COO leading through rapid growth and market expansion. Sophie’s direct reports praise her empowering leadership style, her commitment to their development, and her unwavering advocacy. She hires people for their unique expertise and encourages them to bring their full selves to work, and reminds them of their value even in moments of self-doubt.In this episode, show creator and Fort Light founder Annie Riley sits down with Sophie, and they discuss:What a “founder mindset” really means for employees How to earn the right to dissent How to lead when someone on the team has an unexpected crisis The mindset shift that enabled Sophie to go from managing 3 to 600+ people If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Sophie RuddockConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear
9. Best Manager Ever: Behavioral Science as a Leadership Tool
42:02||Season 3, Ep. 9In this expert episode, Annie Riley sits down with Matt Wallaert, an applied behavioral scientist who made the leap into the tech and startup worlds. Matt is currently the CXO at Oceans, and he’s previously held leadership roles at Clover Health, LendingTree, Microsoft, frog design, and more. Matt explains why all leaders should know and use the principles of applied behavioral science– because all startup leaders are in the business of behavior change with our customers, our teams, and ourselves. They discuss specific tactics that leaders can use to influence their team’s behavior, including the SIDE framework, promoting and inhibiting pressures, iterative experimentation, and more. Matt explains how applied behavioral science can be the key to unlocking lasting and meaningful behavior change, and to achieving a more empathetic and effective leadership style. If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Matt WallaertConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear
8. Worst Manager Ever: Annie’s Scariest Manager Stories
16:50||Season 3, Ep. 8In this special Halloween episode of Best Manager Ever, host Annie Riley recounts the top worst manager moments of her career. Tune in to hear scary manager stories, from tales of micromanagement to vague (and unsettling!) feedback… and even Annie’s own manager missteps. There’s value in learning from the best, and ALSO from the worst! You’ll finish this episode feeling less alone, and even with some actionable lessons to help you avoid the same manager mistakes. If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear