Jerome Dwight

Syntilay CEO: How AI Is Changing Product Design | Ben Weiss

What happens when AI, besides assisting creativity - starts designing the product?In this episode of ChallengerX, Jerome Dwight sits down with Ben Weiss, Founder & CEO of Syntilay, to explore how AI is reshaping footwear design, brand building, and the future of physical products.From using generative AI and 3D printing to rethinking how products get made, Ben shares how he’s building at the intersection of technology, fashion, and entrepreneurship. He also opens up about turning a cold message into a mentorship with Reebok co-founder Joe Foster.0:00 [https://www.youtube.com/watch?v=mQCtqgLHUB0] – Intro2:20 [https://www.youtube.com/watch?v=mQCtqgLHUB0&t=140s] – How Ben Weiss Discovered AI in Footwear Design4:38 [https://www.youtube.com/watch?v=mQCtqgLHUB0&t=278s] – Inventing a Whole New Category7:43 [https://www.youtube.com/watch?v=mQCtqgLHUB0&t=463s] – Outplaying the Competition in a Crowded Market9:56 [https://www.youtube.com/watch?v=mQCtqgLHUB0&t=596s] – From Cold Message to Mentor: Meeting Reebok’s Joe Foster12:00 [https://www.youtube.com/watch?v=mQCtqgLHUB0&t=720s] – The Power of Cold Calling and Discipline14:11 [https://www.youtube.com/watch?v=mQCtqgLHUB0&t=851s] – Spotting When You’re on to Something Big16:26 [https://www.youtube.com/watch?v=mQCtqgLHUB0&t=986s] – The Future of AI in Footwear19:01 [https://www.youtube.com/watch?v=mQCtqgLHUB0&t=1141s] – Overcoming Setbacks and ChallengesEssential viewing for founders, executives, and operators navigating growth. // LINKS // Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight #ChallengerX [https://www.youtube.com/hashtag/challengerx] #ChallengerMindset [https://www.youtube.com/hashtag/challengermindset] #Leadership [https://www.youtube.com/hashtag/leadership] #Entrepreneurship [https://www.youtube.com/hashtag/entrepreneurship] #BusinessGrowth [https://www.youtube.com/hashtag/businessgrowth] #OperatorMindset [https://www.youtube.com/hashtag/operatormindset] #ExecutiveLeadership [https://www.youtube.com/hashtag/executiveleadership] #ScalingUp [https://www.youtube.com/hashtag/scalingup] #TeamExecution [https://www.youtube.com/hashtag/teamexecution] #GrowthMindset [https://www.youtube.com/hashtag/growthmindset]

BILL CEO: The Hardest Part of Building BILL Was Becoming the Leader It Needed | René Lacerte

In this episode, we sit down with René Lacerte, founder and CEO of BILL, the financial automation platform serving hundreds of thousands of businesses. What started as a bold idea to fix broken, manual financial workflows has grown into a company generating around $1.5B in annual revenue with a market cap of roughly $5B. René shares what it really means to carry CEO responsibility at scale. He talks about why even top leaders need CEO coaches, how culture becomes your true competitive edge, and how to balance patience with urgency. As he puts it, “The best ideas always seem obvious in hindsight.”0:00 [https://www.youtube.com/watch?v=5WtMmTDeSsw] Intro2:27 [https://www.youtube.com/watch?v=5WtMmTDeSsw&t=147s] The Problem That Sparked BILL6:30 [https://www.youtube.com/watch?v=5WtMmTDeSsw&t=390s] What Made You Actually Take the Leap?9:53 [https://www.youtube.com/watch?v=5WtMmTDeSsw&t=593s] How BILL Survived — and Won — in a Tough Market13:32 [https://www.youtube.com/watch?v=5WtMmTDeSsw&t=812s] The Hardest Leadership Lessons17:05 [https://www.youtube.com/watch?v=5WtMmTDeSsw&t=1025s] Scaling Strategy: Playing the Long Game23:42 [https://www.youtube.com/watch?v=5WtMmTDeSsw&t=1422s] Why Culture Decides the Outcome27:24 [https://www.youtube.com/watch?v=5WtMmTDeSsw&t=1644s] Speed vs. Impatience: A Founder’s Dilemma36:01 [https://www.youtube.com/watch?v=5WtMmTDeSsw&t=2161s] How Will BILL Be Remembered?Essential viewing for founders, executives, and operators navigating growth. // LINKS //Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight Spotify https://open.spotify.com/show/47yRU8V.. [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbmtvcDVhVkRmQmpvbERQVzZjWjVRY3BjX2ZkZ3xBQ3Jtc0ttWHptTmpOUVU2eGc0SV9ZUldzcUFHZTZ5a2poZllJTVYwRV82ekgtYlZZSnZUSC1lbUNkcXFjbklSRVBWMUYwWjNTUmdfdlg0ckhJdGxFZy1NaGhrMW1TY3U2dWVYdk1ZWkZ0T25YdldnMkxqS1ZJUQ&q=https%3A%2F%2Fopen.spotify.com%2Fshow%2F47yRU8V..&v=5WtMmTDeSsw].#Renélacerte [https://www.youtube.com/hashtag/ren%C3%A9lacerte] #Bill [https://www.youtube.com/hashtag/bill] #fintech [https://www.youtube.com/hashtag/fintech] #FutureOfWork [https://www.youtube.com/hashtag/futureofwork] #leadership [https://www.youtube.com/hashtag/leadership] #leadershiptraining [https://www.youtube.com/hashtag/leadershiptraining] #ChallengerMindset [https://www.youtube.com/hashtag/challengermindset] #AI [https://www.youtube.com/hashtag/ai] #TechLeadership [https://www.youtube.com/hashtag/techleadership] #ScalingUp [https://www.youtube.com/hashtag/scalingup] #BusinessGrowth [https://www.youtube.com/hashtag/businessgrowth] #OperatorMindset [https://www.youtube.com/hashtag/operatormindset] #TeamExecution [https://www.youtube.com/hashtag/teamexecution] #JeromeDwight [https://www.youtube.com/hashtag/jeromedwight] #challengerx [https://www.youtube.com/hashtag/challengerx] #motivation [https://www.youtube.com/hashtag/motivation]

Altair Former COO: Scaling a $10B Tech Company Through 35 Acquisitions | Stephanie Buckner

How do you scale a tech company from $3.6B to nearly $10B and lead 35+ acquisitions without breaking the organization?In this episode of ChallengerX, Jerome Dwight sits down with Stephanie Buckner, former COO of Altair Engineering and now Co-Founder of Escape Investment Management, to unpack the real operational, leadership, and M&A lessons behind hyper-growth in deep tech.0:00 [https://www.youtube.com/watch?v=M-JQtbmXbPc] Intro2:26 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=146s] What drew you to the world of tech?4:40 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=280s] Navigating your early career6:07 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=367s] Returning to Altair and the path back8:58 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=538s] The major transformational milestones at Altair15:26 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=926s] The North Star priorities that guided your leadership18:17 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=1097s] What you looked for when building your leadership team20:30 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=1230s] Managing the exit to Siemens23:08 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=1388s] What led you to become an investor28:37 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=1717s] Your strongest convictions when evaluating investments30:44 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=1844s] The KPIs companies should focus on34:00 [https://www.youtube.com/watch?v=M-JQtbmXbPc&t=2040s] Lessons for the next generation of leadersEssential viewing for founders, executives, and operators navigating growth. // LINKS //Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight #Stephaniebuckner [https://www.youtube.com/hashtag/stephaniebuckner] #Altair [https://www.youtube.com/hashtag/altair] #engineering [https://www.youtube.com/hashtag/engineering] #FutureOfWork [https://www.youtube.com/hashtag/futureofwork] #leadership [https://www.youtube.com/hashtag/leadership] #leadershiptraining [https://www.youtube.com/hashtag/leadershiptraining] #ChallengerMindset [https://www.youtube.com/hashtag/challengermindset] #AI [https://www.youtube.com/hashtag/ai] #TechLeadership [https://www.youtube.com/hashtag/techleadership] #ScalingUp [https://www.youtube.com/hashtag/scalingup] #BusinessGrowth [https://www.youtube.com/hashtag/businessgrowth] #OperatorMindset [https://www.youtube.com/hashtag/operatormindset] #TeamExecution [https://www.youtube.com/hashtag/teamexecution] #JeromeDwight [https://www.youtube.com/hashtag/jeromedwight] #challengerx [https://www.youtube.com/hashtag/challengerx] #motivation [https://www.youtube.com/hashtag/motivation]

Asana COO: Transforming the Way Companies Operate | Anne Raimondi

In this episode, Anne Raimondi, COO of Asana and a seasoned operator across companies like eBay, SurveyMonkey, Zendesk, and Guru — breaks down what it really takes to lead teams and build products in a world being reshaped by technology. Anne didn’t begin her career in tech. She found her way into the industry by solving real operational problems inside a retail company, and that experience shaped how she thinks about technology today: as a tool that should make people more effective, not overwhelmed. From scaling eBay during its explosive growth, to defining product-led culture at SurveyMonkey, to transforming customer experience at Zendesk, Anne shares the lessons she’s carried across decades of building, leading, and operating inside some of the most influential companies of the last twenty years. Now as COO of Asana, she’s helping redefine how teams work in an era where AI, automation, and collaboration tools are changing expectations faster than ever. In this conversation, Anne breaks down: - The mindset shift leaders need as work becomes increasingly tech-enabled - Why companies must remove friction — not add complexity - How to build teams that stay innovative as organizations scale - Why your product is your brand (especially as customer expectations accelerate) // LINKS // Instagram https://www.instagram.com/jeromedwightx Youtube https://www.youtube.com/@jeromedwightx TikTok https://www.tiktok.com/@jerome.dwight Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39 #AnneRaimondi #Asana #FutureOfWork #Leadership #ChallengerMindset #AI #TechLeadership #ScalingUp #BusinessGrowth #OperatorMindset #TeamExecution #JeromeDwight #ChallengerX

Mindvalley COO: How AI Is Transforming Leadership, Education, and Culture | Alex Dogliotti

In this episode, Alex Dogliotti, Chief Operating & Human Resources Officer (COO) of Mindvalley, shares how the company is redefining education and leadership in the age of AI. He explains why the future belongs to leaders who can bridge technology and people, and how he guides one of the world’s leading edtech companies, impacting 20 million learners across 135 countries With a community spanning millions, Mindvalley’s mission has always been clear: to unlock human potential through transformational education. But as AI reshapes industries, Alex explains how Mindvalley is evolving—blending technology, emotional intelligence, and purpose-driven systems to build the future of learning. Alex discusses what he calls “The Future Human”—where mindset, technology, and health converge to help people live longer, smarter, and more fulfilled lives. He dives into how AI is disrupting traditional education, why emotional learning still matters, and how leaders can integrate AI without losing the human element that drives connection and culture. For founders and executives, this episode is a roadmap for future-proofing your organization—where innovation isn’t just about adopting new tools, but reimagining how humans and AI can grow together We cover: - How Mindvalley evolved from an education company to a transformation platform - Why AI will reshape learning, leadership, and HR as we know it - How to train AI as if it were part of your team—not a replacement for it - How to balance technological progress with human connection // LINKS // Instagram https://www.instagram.com/jeromedwightx YouTube https://www.youtube.com/@jeromedwightx TikTok https://www.tiktok.com/@jerome.dwight Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39 #AlexDogliotti #Mindvalley #AILeadership #FutureOfLearning #Transformation #DigitalLeadership #ChallengerX #Innovation #FutureHuman #BusinessStrategy #AIMindset #OrganizationalDesign #FounderMindset #LeadershipEvolution #HumanPotential