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Winning Season

Winning Season is the go-to podcast for mid-career professionals who want strategy, not just a pep talk. Every episode hands you something you can use Monday morning a way to negotiate, to be heard in the room, to reset when the plan falls apart. Part framework, part candid conversation. The energy of a professional girlfriend who happens to have trained 10,000+ people on four continents and will absolutely give you the game.

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Map Your Ascent: Ashwini Balasubramanian on Change, Vulnerability, and Building Influence

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 mode…

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Kristine Frost: Generosity, the C-Suite, and the Season After the Title

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…

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From Soccer Fields to Corporate Floors: How One Woman Turned Grief Into a Gateway of Purpose

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…

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You're Never Stuck: Erica Rooney on Curiosity, AI, and the Questions That Change Everything

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 surprisingly…

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Embracing Service, Leadership, and Ubuntu: An Inspirational Journey with Hermence Matsotsa

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 humility…

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This Is How You Love Her: A Radical Journey to Self-Love with Traci Saulsberry

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 meaning…

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Unlocking Leadership and Community Impact with Alison Anthony

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…

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Why Standing in Your Power Is Not One-Size-Fits-All And How to Find Yours

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…

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The Real You vs. Work You: Why 61% of Us Are Hiding at Work

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…

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Call and Response: Leadership Lessons w L. Michelle Smith

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 philosophy The…

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