Latest episodeOct 9, 2026
Why the Best Founders Spot Opportunities Others Miss in Plain Sight
With Cameron Hardesty
The Winning Season Podcast · 317+ Episodes
Find the win in every season.
Strategy, not just motivation. Host Jacqueline V. Twillie sits down with leaders and hands you the real tools: negotiation, presence, and resilience, so you can lead with clarity and advocate for your worth.
317+
Episodes
2017
On air since
Forbes
Must-listen
86
Guests
The show
A show for the in-between seasons.
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 has coached leaders at Fortune 500 companies, government agencies, and startups for more than a decade and will absolutely give you the game.
Your host
Jacqueline V. Twillie
Executive strategist · Bestselling author
She built the L.A.T.T.E. negotiation framework and has spent her career walking in when the decisions are hard and the stakes are real.
- 3x bestselling author, incl. Don’t Leave Money on the Table
- Coached leaders at Fortune 500 companies, government agencies & startups
- Featured in Forbes, NPR, Fast Company & Essence
- Frameworks: L.A.T.T.E. · R4 · A.H.A.
Hosted by
Jacqueline V. Twillie
Leadership strategy for the season you’re in.
Her question for guests: What’s the win in any season? Answer it on the guest form.Episodes317
Since 2017
First episode: Dec 27, 2017
Seven places to start
Start with what you’re facing.
Episodes are filed by the problem they help with, and some sit under more than one.
All 317 episodes- Episodes163Leadership,
Lead with clarity.
Newest- The 5 Cs of Uncomplicated Leadership Every Manager Needswith Julia Rock · Sep 18, 2026
- Map Your Ascent: Ashwini Balasubramanian on Change, Vulnerability, and Building Influencewith Ashwini Balasubramanian · Aug 17, 2026
- Kristine Frost: Generosity, the C-Suite, and the Season After the Titlewith Kristine Frost · Jul 31, 2026
- Episodes86Resilient leadership,
A way to reset when the plan falls apart.
Newest: Oct 9, 2026 - Episodes75Your next move,
Mid-career strategy
Make the next move deliberate.
Newest: Oct 9, 2026 - Episodes53Salary negotiation,
Prepare, ask, and hold your number.
Newest: Sep 28, 2026 - Episodes58Executive presence,
Be heard in the room.
Newest: Sep 28, 2026 - Episodes13Leadership for Black women,
Advocate, lead, and thrive as the only one in the room.
Newest: Feb 10, 2026 - Sessions2Applied AI,
The AI agent drafts. You decide and send.
Newest: Oct 8, 2026
The guests
Leaders who have sat down with Jacqueline.
97 episodes with a named guest since 2018. Each name opens one.
Browse episodesLately on the show
- Cameron Hardesty, founders
- Melanie White, trust your gut
- Julia Rock, managers
- Kelvin B Henry, comebacks
- Ashwini Balasubramanian, change and influence
- Kristine Frost, the season after the title
- Guerlyne Guercy, grief into purpose
- Erica Rooney, curiosity and AI
- Hermence Matsotsa, service, newest of 2 episodes
- Traci Saulsberry, self-love
Show all 86 guestsShow fewer guests
- Alison Anthony
- Denise Foss
- Suezette Yasmin Robotham
- L. Michelle Smith
- Alair Castro, newest of 2 episodes
- Lexie Mendelson
- Fadjanie Cadet
- Shannah Compton Game, newest of 3 episodes
- Dr. Jacqueline Ashley
- Erica Franklin
- Dr. Angie Mason
- Dr. Tyre Patterson
- LaDondra Wilson, newest of 2 episodes
- Manessa Lormejuste, newest of 3 episodes
- Jasmin Brand, newest of 2 episodes
- Gala Jackson Dobbins
- Sevilla Washington Dawson
- Gigi McDowell
- Cheryl Monroe, newest of 3 episodes
- Dr. Erin Wheeler, newest of 2 episodes
- Vanne McMillan
- Stacey Guillén Bridges
- Whitney L. Barkley, newest of 3 episodes
- Arthur Little, newest of 2 episodes
- Vhutali Nelwamondo, newest of 2 episodes
- Emefa Boamah
- Jessica Heer
- Latosha Bruff
- Nekpen Osuan Wilson
- Kartisia "KC" Esco
- Charmika Placide
- Karla Pámanes
- Janell Hazelwood
- Jennifer White
- Daveda Schmidlin
- Lucy Dazilma
- Tawana Anderson
- Karen Laos
- Maxie McCoy
- Jodi-Ann Burey
- Jazmine Reed-Clark
- Robert H. Johnson Jr., newest of 2 episodes
- Rochelle Porter
- Porsche Williams
- Julie Kratz
- Ashley Cash
- Paloma Alvarado
- Amber Freeland
- Lindsey Perez
- Dr. Michelle Travis
- Delanie Majors
- Shireen Abdullah
- Keyana Simmons
- Stephanie Robertson
- Kathleen Toplin
- Dr. Marie Alcazar
- Dawn Christian
- Dr. Martinique Perkins Waters
- Alicia A.M. Morgan
- CeCelia Thomas
- Shaymaa Alsahhar
- Sheryl Kline
- Dr. Charmaine Gregory
- Jackie Clarke
- Trudie German
- Pervis Taylor, III
- Kelli Kelley
- Annette Wynn
- Deja Foster
- Markitta Gaston
- Ahyiana Angel
- LaConya Murray
- Alexa Crisa
- Kendra Barnes, newest of 2 episodes
- Emerald Sparks
- Catherine L. Wheeler
317 episodes, since December 2017
97 of them with a guest.
Where to listen
Start with the latest.
Play latest, S26 E14All platforms on Podnews (opens in a new tab)Applied AI
Build your first AI agent in one hour.
Jacqueline V. Twillie has taught more than 400 people to build their first AI agent. In September 2026, Forbes featured her as one of the peer leaders closing the $5.5 trillion AI skills gap.
Live session
Build a Chief of Staff and a Content Manager AI Agent
Jacqueline V. Twillie builds two AI agents live: a Chief of Staff for your inbox and calendar, a Content Manager for your week. They draft. You send.
See the sessionLive session
Build Your Negotiation Prep AI Agent in One Hour
Prepare for a salary or contract negotiation in one hour. Jacqueline V. Twillie's live L.A.T.T.E. AI agent build, with the steps and three lines to say.
See the sessionFeatured Episodes
Top performers + fresh drops
Listener favorites
A Powerful Practice for the Mindful & Resilient LeaderTop episode
Resilience
with Emefa Boamah
with Emefa Boamah
617plays
Fresh from the mic
In their own words.
What guests and listeners say after they hit play.
“
Jacqueline gives you the game! Literally breaking down tangible steps you can use right now to negotiate, prepare and position yourself for the job, salary, and many other takeaways.
Jonathan Speaks
“
Jacqueline offers clear, strategic and relevant advice. This podcast will make you evaluate your worth and make sure you are valued in your career. Her guests are amazing and knowledgeable.
Whitney Barkley
“
I am inspired by your topics and your seriousness in addressing them. You give voice to women who are not always able to speak up for themselves.
LeadingFromTheFront
For potential guests
Come have the conversation only we could have.
Winning Season features leaders with a real story about strategy, negotiation, and the wins inside hard seasons. If that’s you, pitch yourself.
For partners & sponsors
Reach an audience that acts on what they hear.
317+ episodes, a Forbes-recognized platform, and listeners who are mid-career professionals making real career moves. Let’s build a partnership.
The Resilient Leader Insder
Keep winning between episodes.
Curated roles, negotiation tactics, and leadership strategy for senior professionals. One email a week, from Jacqueline. Free.