
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 unpack that feedback and to dig into their leadership playbook and lessons learned.
Episodes
Self-Compassion Break for High Performers
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
Speed to Signal with JZ - Laurel CPO
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
How "Temporary Permanent" Drives Progress
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
Ex-Pinterest & Canva Exec: Curiosity As A Muscle
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 Lopez03:48 —
Unblock Your Team with Powerful Questions
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
Top CEO Coach On The Difficulty of Empathizing Up
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
“Smart Rats”: Belief Boosts Performance
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
Be Champagne, Not Flat Soda
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
Get Yourself Some “Boast Bitches”
“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
Time Kills Follow-Up: Share Context Now
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 mi
Bad Meetings Are Disrespectful
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
A Manager’s Word Has To Mean Something
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
COO of Headspace: Why You Should Re-Recruit Yourself
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
Welcome to Season 4
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
Best Manager Ever: Santa
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 thei
Best Manager Ever: Top Takeaways From Season 3
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 notic
Best Manager Ever: Jared Erondu – Hard Mode Leadership
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
Best Manager Ever: Dana Lawson - Conquering Imposter Syndrome and Fostering Team Resilience
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 compass
Best Manager Ever: Amit Shah - Building Trust Through Gratitude
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 a
Best Manager Ever: Patrick Reynolds - Creating the Conditions for Success
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 tho
Best Manager Ever: Sophie Ruddock – Showing Up for Your Team During Crisis
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
Best Manager Ever: Behavioral Science as a Leadership Tool
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–
Worst Manager Ever: Annie’s Scariest Manager Stories
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
Best Manager Ever: Amy Jenkins - Context and Connection Before Content
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 partne
Best Manager Ever: Adam Fishman - The Right Way to Ask for Feedback
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. H
Best Manager Ever: Lauren Gold - The Triple Goal: Learning, Contribution, Fun
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 eve
Best Manager Ever: Charlie Coglianese - The Struggle is Real, But So is the Growth
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
Best Manager Ever: Karin Simelaro - Scale Smarter: Building Teams That Thrive at Every Stage
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 suc
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 ana
Best Manager Ever: Stevie Case - Empowering Leaders by Embracing Authenticity and Trust
Stevie Case is the Chief Revenue Officer at Vanta. Stevie started her career as the world’s first female pro gamer, and then found her way into the tech and startup world through a self-described “winding path”. Prior to Vanta, Stevie had a successful chapter at Twilio, where she started as an individual contributor and then grew to be the VP of Mid-Market Sales.Stevie’s direct reports consis
Welcome to Season 3 of Best Manager Ever
Best Manager Ever shares unfiltered leadership lessons and actionable advice from the most successful and beloved leaders in the startup and tech worlds. This season, you'll hear honest, insightful interviews with operators who’ve been nominated by their teams as the best manager they’ve ever worked for. And for the first time, we’re adding interviews with experts who’ve gone deep on the
Best Manager Ever: Standout Lessons from Season Two
In this solo episode of Best Manager Ever, host Annie Riley of Fort Light takes a moment to reflect on the standout lessons from Season Two.Annie revisits the powerful insights shared by this season’s guests—from hiring people who challenge you, to seeking out dissenting views, to nurturing both personal and team growth. It’s a chance to pause, look back, and celebrate the wisdom and warmth these
Best Manager Ever: Sruthi Lanka - Hire People That Scare You
Sruthi Lanka serves as CFO of Public, an investing platform that allows everyone to invest in stocks, ETFs, crypto, and alternative assets, like fine art and collectibles—all in one place. Prior to Public, she was VP Finance at MoneyLion, a consumer lending platform that listed on NYSE via SPAC in 2021. Her previous career was in investment banking at the Royal Bank of Canada and technology at Gol
Best Manager Ever: Asheesh Birla - Embracing Risk and Cultivating Talent
Asheesh Birla is an Entrepreneur, Angel Investor and Ripple Board Member. Asheesh joined Ripple in 2013 when the team was fewer than ten people. He had a decade-long journey of building Ripple on the product team, and he continues to stay connected to the company as a member of the board. Asheesh’s direct reports admire his passion, strategic vision, and ability to cultivate a positive
Best Manager Ever: Lauren Rhode - Grit, Teamwork & Humility
Lauren Rhode is the VP of Sales at Webflow, and she’s had several interesting chapters to her career. Lauren got her start in public service, working at the Department of Defense. She also played on the national rugby team, and traveled around the world competing for Team USA. She started her tech career in product, before discovering her knack for sales. She has held prior roles at Bablestreet (f
Best Manager Ever: Leanna Nazzisi - From Part-Time to Power Player
Leanna Nazzisi is the Senior Direct of Customer Experience at Victoria Beckham Beauty, a clean beauty, cruelty-free, digital-first makeup and skincare brand. Leanna launched her startup career as a seasonal contractor with Birchbox, where she rose through the ranks to become a senior CX leader as the company scaled. She also had a chapter as a customer success leader during Zendesk’s growth stage.
Best Manager Ever: Amit Shah - Harnessing Energy, Gratitude & Learning
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 a
Best Manager Ever: Liz Ludwig - Leading with Momentum and Empowerment
Liz Ludwig is the co-founder of Takes, a game for sports fans. Liz started out working in Fortune 500 companies, before moving into the startup world. She had a successful career building and scaling marketing functions at Sungevity, OhmConnect, and more. Liz’s direct reports describe her as a high-energy manager who builds momentum, trusts her team quickly, empowers them, and balances result
Best Manager Ever: Luis Duarte - Build Your Own Mold
Luis Duarte is the CEO and co-founder of Amoofy, an AI-guided storytelling platform. Luis has a rich background as a three-time entrepreneur, and a leader in philanthropy and impact investing. Luis's direct reports describe him as an amazing listener, who is able to bring a sense of calm to chaos. They praise his willingness to take on short-term challenges for long-term gains and his focus o
Best Manager Ever: Carol Mahoney - Human First Leadership
Carol Mahoney is a seasoned Chief People Officer. She’s well known for her work operationalizing the famously beloved company culture at Gainsight. She’s also served as the SVP of People and Culture at Zoosk and SVP of HR at LivingSocial, among others.Carol's direct reports praise her ability to get things done, while creating a positive culture and showing up as her authentic self. She is recogni
Best Manager Ever: Helen Min - Scaling Impact Through Effective Management
Helen Min is a venture partner at True Ventures, and an investor and advisor to over 50 early-stage enterprise software and fintech companies. Helen has a notable background leading global marketing and communications at companies like AngelList, Plaid, and Quora and was an early marketing leader at Dropbox and Facebook. Helen’s direct reports highlight her genuine care for the team, her supp
Best Manager Ever: Seif Salama - Mastering Your First Manager Role
Seif Salama is the Senior Director of Product Marketing at Fanatics. Seif previously held marketing roles at Carta, AngelList, Affirm, and more. Seif’s direct reports praise his ability to maintain high standards while ensuring the team's morale and his talent for building a diverse and talented team dynamic. They describe him as a leader who, through authenticity and open communication, crea
Best Manager Ever: Hank Taylor - Unconventional Hiring, Learning, and Leading
Hank Taylor is Head of Marketing at Laravel. Hank has been on the ground floor of Marketing and Rev Ops functions at Vercel, Lambda School, GitLab, Neo Technology, and more. He has also been an advisor and fractional marketing leader at several companies through his company, GrowthSprint. Hank’s direct reports describe him as an unconventional leader who cares deeply for his people, encourage
Best Manager Ever: Jully Kim - Influencing, Building a Professional Brand, and Communicating Proactively
Jully Kim is the Senior Director of Technology Excellence at Autodesk and was previously the Senior Director of Engineering Practices at Zendesk. Jully has a track record of excellence in technology enablement and engineering program management. Jully’s direct reports describe her as unique, action-oriented, extremely transparent, and deeply caring. In this episode, show creator and Fort
Best Manager Ever: Anthony Sottile - Embracing Failures and Celebrating Success
Anthony Sottile is the VP of Partner Success at Freewill, a startup that enables free estate planning and has helped individuals commit more than $11B to charity. Anthony's direct reports describe him as down-to-earth and accessible, and emphasize his ability to lead through humor and celebration. In this episode, Annie Riley sits down with Anthony to discuss his insights on creating a t
Welcome to Season 2 of Best Manager Ever
Best Manager Ever shares the secrets of building and leading winning teams from the most successful and beloved leaders in the startup and tech worlds. All guests have been nominated as the “best manager ever” by their direct reports. Before each interview, we collect feedback and stories from their team about how the guest *actually* shows up as a leader. Each episode unpacks that feedback a
Best Manager Ever: Amanda Richardson
Amanda Richardson is the CEO of CoderPad, a technical interview and assessment platform. Amanda built her career in Product, and previously led the product teams and played a critical role in scaling the company at HotelTonight and Prezi. Amanda has built a reputation as a dynamic and direct leader. Her direct reports describe her as transparent, authentic, and someone who fosters trust and v
Best Manager Ever: Namrata Ganatra
Namrata Ganatra, is the Chief Product and Technology Officer at Pipe. She has a notable career in tech and startups, including roles at Facebook, Coinbase, BloomTech Lambda School, PayPal, and Microsoft. Namrata's direct reports praise her for balancing technical expertise with empathetic leadership, and highlight her as a hardworking and inspiring leader with a strong focus on accountability
Best Manager Ever: Mari Nazary
Mari Nazary is the CEO of App Academy, and brings a strong background working at the intersection of product, operations, and learning science at several ed tech companies across different stages. Her team praises her as the best leader they’ve ever had, citing her strengths in systems, process, and talent development. In this episode, Annie Riley, Founder of Fort Light dives into Mari’s
Best Work Self Ever in 2025
In this special New Year's episode of Best Manager Ever, Founder of Fort Light, Annie Riley dives into self-management for leaders. Drawing from personal experience and past interviews with top managers, Annie shares insights on how to set yourself up for success in 2025. Key strategies include taking necessary breaks to avoid burnout, identifying daily activities that bring joy and recharge you,
Best Manager Ever: Santa
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 thei
Best Manager Ever: Alan D'Souza
Alan D'Souza is the Director of Analytics at Credit Karma, and formerly led teams at Lending Club and Upgrade Inc. Known for fostering a culture of fun, hard work, and results, Alan's direct reports recall his empathetic and direct feedback style, along with his ability to inspire and motivate with humor. In this episode, Annie Riley, founder of Fort Light sits down with Alan to discuss
Best Manager Ever: Sara Romero-Heaps
Sara Romero-Heaps is the Chief Product Officer at Seesaw Learning. She has built her career at the intersection of education and technology, and previously led product and content at Nearpod. Sara is known for aligning her team's individual aspirations to business goals, and her direct reports describe her as a visionary and empathetic leader. In this episode, Annie Riley, Founder of Fort Light, d
Best Manager Ever: Thianh Lu
Thianh Lu is the Chief Product Officer at Autograph and is a 3x founder, with one company acquired by WordPress and another by Blockchain.com. He has a unique and well-rounded perspective on leadership, having been in the roles of early employee, later-stage executive, and founder/CEO. Thianh's direct reports praise his empowering and collaborative style, and remember him for building high-tr
Best Manager Ever: Katie Corder- Paul
Katie Corder-Paul is a beloved leader. She’s currently building a portfolio career, as the Head of Operations and Customer Success at early-stage startup levelheaded and the first-ever Executive in Residence at Fort Light. Previously, KCP was an early employee at Guild Education and held leadership roles in ops and customer success at Proof, Nomad, and Sondermind. Katie’s past direct rep
Best Manager Ever: Doug Hanna
Doug Hanna, President & COO at Kustomer and former COO at Grafana Labs, is renowned for his expertise in customer service and operational excellence, having significantly contributed to the growth of companies like Help.com and Zendesk. During his tenure, he helped scale Grafana Labs from a team of 70 to over a thousand employees. Doug's direct reports praise his hyper-rationality, except
Best Manager Ever: Lauren Werner
Lauren Werner is the COO of Shop Shops, a live stream shopping app with a talented team of 50-60 employees across five countries. She is an experienced operations executive with a record of piloting, scaling, and managing new businesses and marketplaces.Lauren is lauded by her direct reports as a stabilizing force with an unflappable presence, known for her empathy, clear communication, and method
Best Manager Ever: Sean Twersky
Sean Twersky is Head of Business Operations at Even Up, and previously Instacart. He has 15+ years of experience that thrives on bringing structure to even the most chaotic situations and scaling for long term success. Sean’s direct reports across various companies describe him as a bright, adaptable leader and a great equalizer who successfully manages diverse teams.On this episode, host Ann
Best Manager Ever: Brittney Hall
Brittany Hall is the Head of Customer Experience at ReMatter, a series A startup. She is also known for her notable work at companies like GoGuardian, People.ai and DataGrail. Over the past decade, Brittney has built a reputation for her outstanding ability to build and scale customer-facing teams from scratch. Brittany's direct reports describe her as an exceptional leader who is clear,
Best Manager Ever: Zayd Badwan
Zayd Badwan is a founding team member and VP of Enterprise at Uplimit. Before joining Uplimit, Zayd scaled the Customer Success team at Coursera. With 15+ years of experience in learning and development startups, he brings insights from working closely with global governments and nonprofits, and industry-leading companies including Google and Salesforce. Zayd is described by his direct report
Best Manager Ever: Morgane Palomares
Morgane Palomares is the VP of Marketing at Vercel, and is known for her significant roles at GitHub, Zendesk and Change.org. Morgane's direct reports praise her exceptional leadership, high standards, and ability to create a trusting and safe environment. They describe her as 'superhuman,' 'aggressive,' and 'a winner,' highlighting her unique ability to balance high demands with personal car
Introducing 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 stor
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