Herding Squirrels

Lucas Liu is the Managing Director at Risecor, a boutique consulting firm specializing in M&A integration, carve-outs, exit readiness, and AI strategy for private equity firms and their portfolio companies. In this episode of Herding Squirrels, Lucas breaks down why so many integrations fall apart at the people level and what leaders can actually do about it before the cracks appear. If you’re nav...

Andrew Matney is a finance, strategy, and M&A operator who has seen transactions from nearly every angle — lender, advisor, investor, and operator. In this episode of Herding Squirrels, he shares what gets missed when everyone is on their best behavior before the close, and why the real operating system of a founder-led business lives in decisions, not documents. If you’re navigating a post-close...

Guest Bio Kamran Jahanshahi is the President and Founder of PeakPoint Consulting, where he helps organizations navigate business transformation, operational excellence, digital strategy, AI adoption, and change management. He brings more than 25 years of leadership experience across Citibank, MetLife, Walgreens Boots Alliance, and his independent consulting work, with deep experience in M&A integr...

Louie Celiberti is the founder of E27 Technology Solutions and spent over 15 years at Guggenheim Partners leading enterprise data and AI transformation at scale. In this episode of Herding Squirrels, he returns to share why most AI pilots fail not because of the technology but because of how organizations approach the work — and what a more deliberate, architecture-first model actually looks like....

Post Body Stephen Szypulski leads post-acquisition integration at Fitch Learning, part of Fitch Group and Hearst Corporation, where the business serves more than 100,000 learners across over 100 countries. In this episode of Herding Squirrels, he walks through why so many M&A deals lose value after close, what actually breaks first when an integration plan meets reality, and why the work of integr...

Episode Overview What actually happens to people after an acquisition closes? Anne-Marie Mills has lived it twice — first as HR lead when Algorithmia was acquired in 2021, and again in a more recent transition spanning teams from Seattle to Eastern Africa. In this episode, Anne-Marie walks through both experiences with real honesty: the early excitement, the culture shock six months in, the attrit...

Frédéric Rivain is the CTO at Dashlane, a leading cybersecurity company — which means when AI coding tools started flooding the market, his team had more reasons to be skeptical than most. In this episode of Herding Squirrels, Frédéric walks us through how Dashlane built real AI adoption across an engineering org that had legitimate security concerns about the tools, why the hardest part of the ro...

Episode Overview What 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 bes...

Episode Overview Your 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...

Guest Bio Boomie 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...

Herding Squirrels Episode 17: Rosemary Sanchez on Leadership, Team Mergers, and Thriving Through Chaos Rosemary 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 prod...

Herding Squirrels Podcast: Jossie Haines on Leadership Transitions and Leading Through Change Episode Overview You’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 pill...

Herding Squirrels Podcast: Harini Rajagopal - Building Resilient Teams Without Burning Out Guest Bio Harini 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, H...

Herding Squirrels Podcast: Adam Tal - Building Teams That Thrive in Complexity Guest Bio Adam 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...

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 navig...

Leading Through Change: The Path Forward is Through In 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,...

Episode Overview Nicole 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 uncerta...

When Your "Band of Misfits" Becomes an Engineering Powerhouse Your 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...

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 s...

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 & Timestamps 00:00 - 01:11 - Personal Introduction Build Allison buil...

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 alignme...

Episode Overview In 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 demonstra...

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...

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 i...

Herding Squirrels Episode 3: Building Bridges and Breaking Patterns with Cole Christie In 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 in...