Best Manager Ever

What if the secret to great leadership is actually learning to say no? Annie Riley sits down with Gautam Prabhu, VP of Engineering at Scribe AI and longtime startup operator, to unpack his lessons from 25+ years of building teams at PagerDuty, Zendesk, and Opentrons. Gautam talks through why leaders should treat every “yes” as a promise, how winning teams are built through systems (not heroics), why a bad decision is better than no decision at all, and how he builds trust through honesty and accountability.Time Stamps:00:00 Meet Gautam Prabhu02:11 From engineer to accidental manager05:04 Learning leadership the hard way08:26 The two kinds of trust12:03 Why intent matters first15:42 Competence has to follow19:18 Why great managers say no23:57 A bad decision beats no decision28:41 Startups can’t run on heroes forever33:22 Building systems that scale39:48 What great leadership really leaves behindJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Gautam PrabhuNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

What does it take to lead through 15 years of pivots, mergers, layoffs, and massive growth— without losing your people (or your mind!) along the way? Annie Riley sits down with Karan Singh, co-founder of Ginger and COO of Headspace, to unpack why great managers win people over through curiosity and genuine connection, how managers need to learn to ride the “J-curve” of change, and why everyone should re-recruit themselves to their role. Timestamps:00:00 Meet Karan Singh04:30 Learning to manage on the fly07:20 Winning people over09:25 The mindset for surviving startup chaos12:01 The j-curve of change14:41 Speed vs. Space: giving teams time to process change18:32 Healthy departures 22:24 Creating a “Next Play Plan” 26:49 Why you should re-recruit yourself38:52 Rethinking PIPs: What most people get wrong Join us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Karan SinghNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

Best Manager Ever shares hard-earned leadership lessons from the very best and most successful managers in startups and tech. But here’s the twist: Every guest is endorsed by their team as the “best manager ever.” We talk to the guest’s direct reports to learn how they *really* lead, and then unpack that feedback live with the guest. This season we’re leveling up with world-class experts who have spent their careers studying the science of leadership, including professors, authors, and coaches.Season 4 kicks off March 18th, with new episodes every Wednesday wherever you get podcasts.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

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 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

In 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

Jared 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

Dana 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

Amit 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