Best Manager Ever

After 50 episodes with some of the top leaders in startups and tech, Annie Riley takes a moment to reflect and share her top five leadership takeaways that surfaced again and again throughout the latest season.  Annie also reflects on the current moment—from the rapid rise of AI to the growing need for authentic human connection—and why those realities have only strengthened her commitment to...

The stereotype of the hard-charging executive is hurting performance. Scott Lamb moved to NYC to pursue journalism, but ended up joining Buzzfeed when it was just five people and has been on the startup path ever since. In this episode, Scott sits down with Annie Riley to explore a different model for leadership– one rooted in curiosity, steadiness, psychological safety, and real human connection....

The voice pushing you forward is also holding you back, and your inner critic is costing you more than you think. Annie Riley talks with clinical psychologist and self-compassion teacher Dr. Michael Klein to explore the psychology behind ambition, achievement, and the never-ending pursuit of "more." They discuss why success doesn't automatically lead to happiness, how striving and self-criticism c...

JZ has built product teams at Airbnb, Webflow, Dropbox (and now Laurel), and in this episode she shares her honest leadership playbook and lessons learned. JZ covers why conviction is really about speed to signal, how to move fast without creating chaos, and why great leaders should share uncertainty instead of performing conviction. JZ also shares hot takes about 1:1 meetings, asking for help, an...

Don’t let perfectionist fantasies kill progress. Annie Riley sits down with Anna Randall, Director of Enterprise Sales at Curri and former VP of Sales at TigerEye, Autodesk, and PlanGrid, to explore the power of “temporary permanent” thinking. They break down why the best teams prioritize momentum over precision, normalize imperfect solutions, and keep moving when the path changes. Plus: why the t...

Work is not like school– there are no right answers, and if you’re looking to be “right” then you will always fall behind. Annie Riley sits down with Silvia Oviedo Lopez, Founder & CEO of Blomma AI and former Canva and Pinterest leader, to unpack how the best leaders train curiosity, learn in real time, and see hard questions as a gift. Time Stamps:  00:00 — Meet Silvia Oviedo Lopez 03:48...

Better questions create better teams. Annie Riley sits down with Maayan Roth, Head of Engineering at Crux Climate, to unpack the skill most managers overlook: asking questions that actually move things forward. Maayan shares how to use curiosity to uncover what’s really going on and guide conversations without controlling them. Plus: the traps new managers fall into, the difference between coachin...

Leadership is lonely. Most leaders don’t get enough support or positive feedback. And that includes our own boss too. Annie Riley and top executive coach Ed Batista break down why it’s so hard to empathize up— and how simple shifts like checking in or offering genuine positive feedback can change the dynamic, because sometimes the most powerful move is truly seeing the person behind the role. Time...

You don’t become a great manager by regurgitating frameworks. Management is a craft and a skillset that gets built over time.  Annie Riley sits down with Maura Church, VP of Product & Engineering at Two Chairs, to talk about how a manager’s mindset impacts team performance. From the “Smart Rats” theory to balancing tough feedback with real belief, Maura breaks down how to coach growth, bu...

Building a strong network is a skill. Annie Riley sits down with Whitnie Narcisse, former First Round Capital Partner, to unpack how she has built one of the best networks in Silicon Valley. Whitnie breaks down how to be memorable and build connections that last using her FACE framework (Factual, Authentic, Credible, and Engaging). Plus: why most networking advice falls flat, how to design rooms p...

“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 y...

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 Pang 01:58 Learning as a...

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 re...

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), w...

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 sho...

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...

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 the...

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 no...

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 He...

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 compas...

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...

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 th...

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 unwaverin...

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–...

​​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, a...