Winning Season

What does it take to go from answering phones to running one of the largest convention centers in the country? In this episode, Jacqueline sits down with Joyce Leveston, president and CEO of the Javits Center in New York City, to share her blueprint for women and leadership. Joyce grew up in Cincinnati, Ohio, and moved to San Diego at 19. She watched a convention center being built and talked her...

How do you manage over 32 AI agents to build a new business when you don't have a technical background? Welcome to Part 1 of a special Winning Season mini-pod series! In this kickoff episode, Jacqueline Twillie pulls back the curtain on the exact mindset and strategy she uses to run a fleet of AI agents using Gumloop and Claude . Using plain English (zero tech jargon!), Jacqueline explains how...

Jacqueline sits down with Cameron Hardesty, CEO and founder of Poppy Flowers, to talk about building a nationwide e-commerce wedding florist, raising venture capital, and the mindset shifts that helped her keep going through years of rejection. Cameron shares how curiosity, industry insight, and a steady nervous system helped her spot an overlooked market opportunity and scale a business serving 1...

What does it take to become CEO of a four-generation family business when no one hands you the roadmap? Melanie White, President and CEO of Hellwig Products and current Chairperson of SEMA, joins Winning Season to share how she went from cold-calling in outside sales to the C-suite by doing the job first and asking for the title later. Melanie gets honest about the moments that shaped her: crying...

Most high-achieving women are taught to keep their heads down, do the work, and wait to be noticed. Julia Rock says that mindset quietly kills careers. In this conversation, she reveals the moves that took her from working at ExxonMobil for 12 years to leading a global business, coaching more than 1,000 professionals, and writing Uncomplicated Leadership . Jacqueline and Julia break down the momen...

This conversation is a faith-forward career discussion with Kelvin B Henry, whose background spans the military, Procter & Gamble, PepsiCo, ministry, and coaching. He and Jacqueline Twillie reflect on mentorship, career reinvention, layoffs, AI disruption, and the personal adversity that shaped his book Rise .Kelvin shares the framework behind Rise and how it helped him process setbacks, a can...

Ashwini Balasubramanian, Vice President of R&D for Transportation and Energy Business at 3M and former Harley-Davidson leader, joins Jacqueline to discuss her debut book, Map Your Ascent, and the lived experiences that shaped it. The conversation centers on navigating change, especially through career pivots, motherhood, and moments of personal uncertainty. We discuss how to move from survival...

Kristine Frost grew up in Pontiac, Michigan, in the years when General Motors was pulling out and the families left behind built their own support systems out of mac and cheese, popsicles, and each other. She watched her grandmother, Vienna, run a government-subsidized community while her own health was failing, showing up for refugees and immigrants day after day. That is where Kristine's philant...

Main topics: Guerlyne’s journey from collegiate soccer to executive life Understanding and processing grief beyond loss of loved ones How faith and scriptural reflection sustain us through hard seasons The importance of self-acceptance and owning your identity Practical steps to navigate and transform grief into strength The role of gratitude and thanksgiving in healing Supporting others with comp...

A room full of women builders at MIT asked ChatGPT to draw them based on everything it knew. It drew the same white man over and over. That moment sparked Erica Rooney's new book, The AI Gap, and this conversation. Erica joins Jacqueline as the first AI expert on Winning Season to break down the four gaps quietly widening between who AI was built on and who gets left behind, and the surprising...

Hermence Matsotsa, a global leadership expert, author, and advocate for community-centered health and transformation joins Jacqueline Twillie in Conversation. In this episode, Hermence shares her multicultural background, her journey through global health, and the profound lessons she's learned about service, vulnerability, and interconnectedness. This conversation reveals how embracing humili...

Join us as we dive into Traci Saulsberry's inspiring journey of self-discovery, leadership, and radical self-love. Traci shares powerful insights from her debut book, revealing how vulnerability, curiosity, and authenticity can transform our lives and careers. In this episode: Traci's experience breaking barriers as one of the youngest Black executives at NBC and leading at Peacock The mea...

Summary In this inspiring interview, Alison Anthony shares her journey from corporate leadership to nonprofit impact, emphasizing the power of preparation, authentic communication, and strategic use of AI in advancing community goals. Discover how to leverage your strengths, build trust, and make impactful asks to create lasting change. Key Topics Preparation and strategic planning in negotiation...

Standing in Your Power: A Conversation with Denise Foss on Self-Leadership and Transformation Discover how Denise’s journey from dance to leadership led her to create a powerful deck focused on helping individuals reclaim their strength and authenticity. In this episode, we explore the nuances of standing in your power, navigating unexpected challenges, and cultivating resilience within yourself a...

Discover how authentic leadership, community, and self-awareness can transform your career and life. Suezette shares practical insights, personal stories, and strategies to help you lead fearlessly beyond titles. In this episode: Suezette’s journey from education reform to tech leadership The true meaning of authenticity in leadership How to uncover and eliminate self-imposed dissonance The impact...

Unlock the powerful leadership principles grounded in Black church traditions and culture. In this episode, L.Michelle Smith shares her insights on how call and response, faith, community, and resilience can transform your leadership approach and drive authentic connections. L.Michelle's inspiration behind writing  Call and Response  and how her church experiences shape her leadership philosop...

This episode of Winning Season features a real lesson from Jacqueline V. Twillie , originally delivered live to a group of mid-career professionals. In it, Jacqueline unpacks the moment she cracked a high-stakes global project stalemate by identifying the single metric and timeline that mattered most to a senior leader. She walks listeners through her signature L.A.T.T.E. Framework —Look, Anticipa...

Summary In this episode of the Winning Season podcast, host Jacqueline Twillie interviews Alair Castro, a Director of Diversity and Inclusion Strategy and Marketing at Northwestern Mutual and founder of the AC Consultancy. Alair shares her journey and passion for addressing the racial wealth gap, advocating for Black women, and creating inclusive marketing strategies. The conversation explores the...

Winning Season Podcast - Mini Episode Show Notes Host: Jacqueline Twillie Episode Type: Mini Episode - Career and Negotiation Inspiration Duration: ~3 minutes Episode Overview A quick-hit episode sharing actionable career and negotiation tips from two of Jacqueline's current projects, designed to give listeners a boost in their professional journey. Main Tip: Highlight Your Unique Value Identi...

Summary In this episode of the Winning Season podcast, Lexie Mendelson shares her extensive experience in building partnerships and launching innovative products like Google Pay. She emphasizes the importance of values such as truth and loyalty in partnerships, the need for adaptability in international rollouts, and the significance of aligning diverse stakeholders. Lexie also discusses the chall...

Summary In this episode, Jacqueline Twillie discusses the intricacies of navigating difficult conversations and negotiations. She introduces the Latte Framework, which consists of Look, Anticipate, Think, Talk, and Evaluate, providing practical strategies for each stage. The conversation covers how to observe tension, anticipate derailments, address bad behavior, maintain composure in power imbala...

Summary In this episode of the Confidence Rewired series, Jacqueline Twillie explores the science of self-trust and the mental skill of confidence. She emphasizes that confidence can be trained through neuroplasticity, which allows the brain to rewire itself based on experiences. Jacqueline introduces the 90-day confidence circuit plan, which includes identity anchors, micro actions, and reflectio...

Summary In this episode of the Confidence Rewired series, host Jacqueline Twillie explores the intersection of breath work and confidence, emphasizing the importance of breath in high-stress situations. She introduces cyclic sighing as a powerful technique for reducing anxiety and enhancing leadership presence. The episode also outlines practical steps for incorporating breath work into daily rout...

Summary In this episode of the Winning Season Podcast, the Confidence Rewired Series, host Jacqueline Twillie discusses the importance of dopamine in building confidence and motivation. She introduces the concept of the 'confidence comeback loop' and emphasizes the significance of tiny wins in stimulating dopamine release. Jacqueline provides a practical framework called the 'Tiny Win System' to h...

Summary In this episode of the Confidence Rewired Series of the Winning Season Podcast, host Jacqueline Twillie explores the concept of the 'messy middle' where life and work pressures collide, leading to a dip in confidence. She discusses the neuroscience behind confidence, emphasizing how chronic stress affects the brain's ability to function effectively. Jacqueline introduces the BL...