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PODCAST

Herding Squirrels

Created and Hosted by Brandon Wetzstein

Ever tried to get a group of squirrels to move in the same direction? Welcome to modern teamwork! Herding Squirrels is a podcast that explores the chaotic, wonderful, and sometimes maddening world of teams in our hyperconnected age. From Slack notifications pinging like acorns falling from a tree to the constant scatter of competing priorities, we dive into what makes teams tick. herdingsquirrels.substack.com

business management

All Episodes

21:47

Herding Squirrels Ep 20 w Gowri Sivaraman

Herding Squirrels ·

2025/11/20

Episode OverviewWhat does it take to scale a fintech product from startup to flagship while keeping your team aligned and engaged? Gowri Sivaraman has spent 25+ years answering that question across multimillion-dollar products at companies like Intuit. In this episode, she shares the hard-won wisdom behind building teams that hold each other accountable and have fun doing it—revealing why the best teams never lose sight of their shared vision, how to remove emotion from cross-functional

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25:43

Herding Squirrels Ep 19 w Barninder Khurana

Herding Squirrels ·

2025/11/13

Episode OverviewYour latest team probably isn’t broken—it’s just been handed impossible expectations. Barninder Khurana, CTO of CoverWhale, knows this intimately. After a decade-plus navigating the insurance tech space as CIO of GeoVera and leading digital transformation at ProSight, he’s discovered that most organizational change initiatives fail not because teams lack skill, but because leaders treat transformation like a separate function instead of building it into the team’s DNA.In this

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23:07

Herding Squirrels Ep 18 w Boomie Odumade

Herding Squirrels ·

2025/11/10

Guest BioBoomie Odumade is a senior engineering leader and fractional leader of Engineering who builds high-performing, secure, and resilient engineering organizations. She coaches engineers and engineering leaders, partnering with them to grow their capabilities and reach their goals. Outside of work, she’s active in the tech community, mentors youth, and enjoys salsa dancing, exploring creative adventures with her kid, and building LEGO botanical sets.Episode SummaryIn this episode, Boomie builds

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23:50

Herding Squirrels Ep 17 w Rosemary Sanchez

Herding Squirrels ·

2025/11/06

Herding Squirrels Episode 17: Rosemary Sanchez on Leadership, Team Mergers, and Thriving Through ChaosRosemary Sanchez brings over seven years of leadership experience from a strong technical background, managing both remote and co-located teams through various stages of growth. In this conversation, she shares the story of successfully merging two engineering teams, navigating a high-stakes product launch under time pressure, and the leadership lessons learned from experiencing both her best and

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29:56

Herding Squirrels Ep 16 w Jossie Haines

Herding Squirrels ·

2025/10/29

Herding Squirrels Podcast: Jossie Haines on Leadership Transitions and Leading Through ChangeEpisode OverviewYou’re caught between your team’s needs and executive expectations—and you’re wondering if there’s a better way. Jossie Haines spent 25+ years leading engineering teams at Apple, Zynga, Tile, and American Express, and she’s figured out what actually works. You’ll hear about the three pillars that keep new leaders from drowning, why your engineers need to process change before moving forward,

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23:16

Herding Squirrels Ep 15 w Harini Rajagopal

Herding Squirrels ·

2025/10/23

Herding Squirrels Podcast: Harini Rajagopal - Building Resilient Teams Without Burning OutGuest BioHarini Rajagopal is a data engineering leader who specializes in building scalable, robust data pipelines that manage terabytes of information. She expertly combines software development rigor with strategic execution to drive business value. A recognized thought leader and AWS Game Day champion, Harini is a frequent speaker sharing expertise on building resilient data teams and preventing burnout

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18:48

Herding Squirrels Ep 14 w Adam Tal

Herding Squirrels ·

2025/10/22

Herding Squirrels Podcast: Adam Tal - Building Teams That Thrive in ComplexityGuest BioAdam Tal is the Director of Payments Engineering at Vimeo, where he’s spent the past five years leading the teams responsible for Vimeo’s global commerce systems—from billing and payments to fraud prevention and compliance. His career spans multiple industries including fintech, edtech, fashion, and consulting, giving him a unique cross-industry perspective on how technology and business intersect. Adam is

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22:31

Herding Squirrels Ep 13 w Oliver Gray

Herding Squirrels ·

2025/10/06

Oliver Gray, Director of Engineering at Trustpilot, shares his journey of transforming underperforming engineering teams into high-performing, self-directed powerhouses. Through hands-on LEGO models, Oliver reveals the power of bottom-up mission development, the pitfalls of fixed-price consulting projects, and why the best thing you can do as a leader is make your team stop needing you. From navigating AI adoption to creating psychological safety in hybrid environments, this conversation offers

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24:06

Herding Squirrels Ep 12 w Louie Celiberti

Herding Squirrels ·

2025/09/19

Leading Through Change: The Path Forward is ThroughIn this engaging episode, Louie Celiberti, Managing Director and Head of Software Engineering at Guggenheim Partners, shares his insights on leadership through uncertainty, building cohesive teams, and navigating generational differences in the modern workplace. Through LEGO models, Louie demonstrates powerful concepts around servant leadership, embracing risk, and the cultural shifts happening in technology teams.Show Notes with Timestamps0:23 -

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19:03

Herding Squirrels Ep 11 w Nicole Tibaldi

Herding Squirrels ·

2025/09/16

Episode OverviewNicole Tibaldi, Engineering Director at The New York Times, joins us to explore what makes teams truly exceptional. Through LEGO builds that visualize team dynamics, Nicole shares powerful insights from her decade-plus experience leading teams at CircleCI, Gatsby, and now the Times. You'll discover why the "shortcuts" to psychological safety don't work, how to lead through uncertainty when there's no playbook, and Nicole's surprising take on what went wrong when leadership used

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26:07

Herding Squirrels Ep 10 w Val Akkapeddi

Herding Squirrels ·

2025/08/08

When Your "Band of Misfits" Becomes an Engineering PowerhouseYour most unconventional team member might be your secret weapon. Your weirdest hire could drive your biggest breakthrough. Ready to stop building cookie-cutter teams?This week on Herding Squirrels, Val Akkapeddi (Director of Engineering at Collectors) builds some eye-opening models about why the quirkiest teams often deliver the most extraordinary results.What You'll Discover:The Don Quixote Leadership Philosophy - Why chasing your own

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23:46

Herding Squirrels Episode 09 w Ilia Lazebnik

Herding Squirrels ·

2025/08/06

Ilia Lazebnik is the Director of Infrastructure at Placer.ai, where he leads the engineering teams behind their large-scale cloud systems. With over a decade of experience in DevOps, cloud architecture, and automation, Ilia is known for driving innovation, building robust infrastructure, and championing modern engineering practices. He’s a HashiCorp contributor and a passionate advocate for open source and tech community knowledge-sharing.For more Ilia:LinkedinGithubEpisode Timeline[00:00:00] -

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17:43

Herding Squirrels Ep 08 w Allison McHenry

Herding Squirrels ·

2025/07/22

Allison McHenry is currently serving as the CTO of Daily Kos, a progressive political blog. Previously, she was CTO at The Daily Beast, and has also held leadership roles at Meta and The New York Times. She most loves thinking about ways to enable teams to use technology to move socially conscious businesses forward.Key Moments & Timestamps00:00 - 01:11 - Personal Introduction BuildAllison builds a rotating model representing herself in the center trying to connect with her four daughters - two

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25:30

Herding Squirrels Ep 07

Herding Squirrels ·

2025/07/16

In this engaging episode, we explore leadership through the lens of technical teams with Dave Walters, former CTO of Hired, Lacalle Group, and Spa Finder Wellness. With 13+ years at The Knot Worldwide (XO Group) and 20+ years as a volunteer firefighter, Dave brings unique perspectives on leading high-stakes teams. Using LEGO® Serious Play® methodology, Dave shares powerful insights on team alignment, staying calm under pressure, and nurturing collective success.About Dave WaltersDave Walters is the

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24:59

Herding Squirrels Ep 06 w John Fly

Herding Squirrels ·

2025/05/26

Episode OverviewIn this engaging episode, we explore leadership through the lens of trust and vulnerability with John Fly, CTO of FirmPilot. Using LEGO® Serious Play® methodology, John shares powerful stories from his 25+ years in technology leadership, revealing how his approach evolved from technical perfectionism to collaborative partnership.Through hands-on building exercises, John demonstrates key leadership principles including taking responsibility for failures while sharing credit for

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20:21

Herding Squirrels Ep 05 w Jessica Mosley

Herding Squirrels ·

2025/05/21

Meet Jessica Mosley, a quality engineering virtuoso who’s been wrangling tech teams, dodging bureaucracy, and making waves in the software world for over 20 years. She’s got the kind of experience you just can’t fake, having tackled everything from software development to DevOps, IT, and Customer Experience. If there’s an inefficiency lurking in a process, Jessica’s the one to spot it, and she’ll do it with a grin and maybe just a touch of sarcasm.But don’t let her laid-back style fool you

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27:02

Herding Squirrels Ep 04 w Frédéric Rivain

Herding Squirrels ·

2025/05/13

Frédéric is the Chief Technology Officer at Dashlane, a leading cybersecurity company specializing in credential management and digital identity solutions. With over two decades of experience in tech leadership, Frédéric drives innovation in security and privacy. A passionate advocate for user-centric security, he brings a unique perspective on blending convenience and robust protection for both individuals and businesses.Find Frédéric online and at the Dashlane Blog:

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23:20

Herding Squirrels Ep 03 w Cole Christie

Herding Squirrels ·

2025/04/22

Herding Squirrels Episode 3: Building Bridges and Breaking Patterns with Cole ChristieIn this enlightening episode of Herding Squirrels, host Brandon Wetzstein sits down with Cole Christie, Senior Engineering Manager for Site Reliability Engineering at Gap. With 18 years of experience in tech and 10 years in leadership positions, Cole shares profound insights about team dynamics across various industries.Episode HighlightsThe Art of Team CommunicationCole emphasizes that communication breakdowns are

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29:05

Herding Squirrels 02 w Jiovanni Rosario

Herding Squirrels ·

2025/04/09

Episode OverviewIn this episode, host Brandon welcomes Jiovanni Rosario, Controls Engineering Manager at Amazon. Using LEGO Serious Play methodology, they explore Jiovanni's journey from individual contributor to leader, discussing team dynamics, leadership challenges, and strategies for effective management.Guest BioJiovanni Rosario has worn many hats in the tech industry—controls engineer, sales engineer, and software developer. These days, he manages a team of controls engineers keeping data

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27:34

Herding Squirrels 001 w Giacomo Pallotti

Herding Squirrels ·

2025/04/01

Herding Squirrels Podcast - Episode 001Giacomo Pallotti: Engineering Leadership Through LEGO Serious PlayIn our inaugural episode of Herding Squirrels, we welcome Giacomo Pallotti, VP of Engineering at Everyday Health Group, for a conversation about engineering leadership, team dynamics, and personal growth - all explored through the creative lens of LEGO Serious Play methodology.Episode Highlights:Opening LEGO Tower Build - We kick off with a quick tower-building exercise that reveals Giacomo's

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