Best Manager Ever

Speed beats perfection every time. Annie Riley dives in with Junan Pang, VP of Customer Success at Intercom, to unpack how he gives direct reports the context they need to act independently. He talks through why most leaders under-share, and how quick, imperfect updates unlock better decisions– without drowning the team in meetings or messages.Timestamps:00:00 Meet Junan Pang01:58 Learning as a mindset05:28 Taking intentional steps back08:48 Growth through manager & IC zigzags14:32 Building authentic, long-term relationships18:08 Being in the problem22:32 Fast, imperfect context sharing 31:35 Learning through osmosis 37:26 Feedback as a daily practiceJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Junan PangNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

Meetings can be a real problem when they’re not run well or have the wrong people in them. Julia Bernstein, COO at Brightside Health joins Annie Riley to break down how she audits, redesigns, and even “dress rehearses” meetings to make them actually useful. From cutting unnecessary attendees to auditing recurring meetings regularly, Julia shares her no-BS approach to protecting time and driving results.Timestamps:00:00 – Meet Julia Bernstein02:00 – Translating business into people-first leadership04:50 – Influencing without authority06:30 – Managing diverse teams 07:15 – Building career ladders from day one16:20 – Being involved vs informed20:50 – The meeting audit: cutting what doesn’t work24:50 – Designing better meetings 26:40 – Giving your team real ownership27:20 – No one will set your boundaries for you33:15 – Weekly rituals that keep teams aligned, human, and performingJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Julia BernsteinNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

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 Hosted on Acast. See acast.com/privacy for more information.

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 Hosted on Acast. See acast.com/privacy for more information.

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: [email protected] 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 Hosted on Acast. See acast.com/privacy for more information.

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 Hosted on Acast. See acast.com/privacy for more information.

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:  [email protected] 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 Hosted on Acast. See acast.com/privacy for more information.

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:  [email protected] 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 Hosted on Acast. See acast.com/privacy for more information.

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:  [email protected] 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 Hosted on Acast. See acast.com/privacy for more information.

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: [email protected] 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 Hosted on Acast. See acast.com/privacy for more information.

Patrick 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: [email protected] 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 Hosted on Acast. See acast.com/privacy for more information.

Sophie 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:  [email protected] 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 Hosted on Acast. See acast.com/privacy for more information.

In 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: [email protected] 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 Hosted on Acast. See acast.com/privacy for more information.

​​In 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: [email protected] 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 Hosted on Acast. See acast.com/privacy for more information.

Amy Yamner Jenkins is the Chief Operating Officer at Meadow, which is an early-stage fintech startup working to transform the financial experience for students and universities. Amy started her career as a classroom teacher, and pivoted into startups by working at NewSchools Venture Fund. Before Meadow, she had a long and successful chapter building Education Elements, and then led the partnerships team at Outschool. Amy’s direct reports describe her as an empowering leader, someone who provides useful and constructive feedback, fosters a high-trust environment, and enables team members to grow.In this episode, show creator and Fort Light founder Annie Riley sits down with Amy,and they discuss:Why connection and context should come before content How to notice and combat bias in hiring A simple 2x2 framework to exchange feedback with your team Why you should avoid using common words like “obviously” and “of course” as a leader If you’re interested in sponsoring an episode of Best Manager Ever, reach out: [email protected] us on Substack Connect with Amy JenkinsConnect 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 Hosted on Acast. See acast.com/privacy for more information.