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PODCAST

Best Manager Ever

Best Manager Ever reveals the secrets of successful management and empowers leaders to build winning teams. Join a community dedicated to sharing insights and stories from the most successful and beloved leaders in the startup world. All guests have been nominated as the “best manager ever” by a recent direct report. Before each interview, we go behind the guest’s back to collect feedback and stories from their team about what they’re *actually* like to work for. Then we sit down with the guest to

business careers

All Episodes

47:18

Get Yourself Some “Boast Bitches”

Best Manager Ever ·

2026/04/15

“Polite silence” is a silent killer on teams. Annie Riley sits down with Dorothy Kilroy, Chief Commercial Officer at Oura Ring and former Airbnb to talk about how to invite productive disagreement while fostering psychological safety and how to give direct feedback without making it personal. Plus: the career-changing power of building your own “Boast Bitches”—a trusted circle that advocates for you and helps you grow.TimeStamps:00:38 – Meet Dorothy Kilroy03:20 – Storytelling, mission-driven work,

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47:04

Time Kills Follow-Up: Share Context Now

Best Manager Ever ·

2026/04/08

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

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49:29

Bad Meetings Are Disrespectful

Best Manager Ever ·

2026/04/01

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

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54:59

A Manager’s Word Has To Mean Something

Best Manager Ever ·

2026/03/25

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

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49:52

COO of Headspace: Why You Should Re-Recruit Yourself

Best Manager Ever ·

2026/03/18

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

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1:42

Welcome to Season 4

Best Manager Ever ·

2026/03/11

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

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13:19

Best Manager Ever: Santa

Best Manager Ever ·

2025/12/24

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

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20:24

Best Manager Ever: Top Takeaways From Season 3

Best Manager Ever ·

2025/12/17

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

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52:09

Best Manager Ever: Jared Erondu – Hard Mode Leadership

Best Manager Ever ·

2025/12/10

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

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43:35

Best Manager Ever: Dana Lawson - Conquering Imposter...

Best Manager Ever ·

2025/12/03

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

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48:46

Best Manager Ever: Amit Shah - Building Trust Through...

Best Manager Ever ·

2025/11/26

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,

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39:44

Best Manager Ever: Patrick Reynolds - Creating the...

Best Manager Ever ·

2025/11/19

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

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40:12

Best Manager Ever: Sophie Ruddock – Showing Up for...

Best Manager Ever ·

2025/11/12

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,

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42:02

Best Manager Ever: Behavioral Science as a Leadership...

Best Manager Ever ·

2025/11/05

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

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16:50

Worst Manager Ever: Annie’s Scariest Manager Stories

Best Manager Ever ·

2025/10/29

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

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37:22

Best Manager Ever: Amy Jenkins - Context and...

Best Manager Ever ·

2025/10/22

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

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45:16

Best Manager Ever: Adam Fishman - The Right Way to...

Best Manager Ever ·

2025/10/15

Adam Fishman is a product and growth advisor with 20+ years of experience building and leading startup teams. Adam was on the early team at Lyft, where he served as Head of Growth. He then went on to lead Product & Growth at Patreon and Imperfect Foods, before launching his portfolio career. Adam has been an advisor and fractional leader at ResortPass, Mozilla, HelpScout, Peerspace and more. He is also the creator of FishmanAF newsletter and the host of the Startup Dad podcast.Adam’s direct

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39:46

Best Manager Ever: Lauren Gold - The Triple Goal:...

Best Manager Ever ·

2025/10/08

Lauren Gold is the Chief Customer Officer at Kustomer, an AI-powered CX platform. Lauren began her tech career at Yahoo before joining the early team at Yext, where she rose from individual contributor to SVP of Enterprise Customer Success.Lauren’s direct reports and colleagues describe her as a leader who supports without micromanaging, fosters autonomy, and creates an environment where everyone feels comfortable sharing, learning, and growing. She’s recognized for her attention to detail,

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48:24

Best Manager Ever: Charlie Coglianese - The Struggle...

Best Manager Ever ·

2025/10/01

Charlie Coglianese is the Chief Technology Officer at Paloma Learning, a VC-backed edtech startup using AI to improve student learning outcomes.Charlie started his career in finance, before making the leap into startups. He was the Founder & CEO of a startup called Schoolrunner, which was acquired by SchoolMint. Charlie served as the CTO at SchoolMint post-acquisition before returning to early-stage building in his current roleCharlie's direct reports describe him as a leader who invests deeply

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40:13

Best Manager Ever: Karin Simelaro - Scale Smarter:...

Best Manager Ever ·

2025/09/24

Karin Simelaro is the Chief Revenue Officer at SchoolAI, an AI platform that supports teacher and student success.Previously, Karin served as the Revenue leader at BrainPOP, Pathful, and Seesaw. She was an early employee at Nearpod, where started as the first field sales rep when the company was fewer than 30 people and around $10M ARR, and ultimately grew the business to $100M ARR and a successful exit.Karin’s direct reports describe her as open, transparent, energetic, and having high expectations

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50 results

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