Jacqueline V. Twillie
Jacqueline V. Twillie hosts Winning Season, the show for leaders who want the real tools to negotiate, to be heard, and to advocate for their worth. She is a strategist and builder focused on AI enablement, and she has written three bestselling books. Here is who she is and what she teaches.
The short version
Jacqueline V. Twillie is a leadership strategist, a negotiation expert, and the host of the Winning Season podcast. She has spent more than a decade developing leaders at Fortune 500 companies, government agencies, and startups. Today she is a strategist and builder focused on AI enablement, and she teaches mid-career professionals to build their first AI agent. She trains people to walk into the hard rooms and advocate for themselves with a plan, not a pep talk.
She built the L.A.T.T.E. negotiation framework, the R4 Resilient Leadership Framework, and the A.H.A. leadership method. These are the tools she teaches on the show, in her books, and in the training rooms of Fortune 500 companies, government agencies, and startups.
The work she is known for
Jacqueline is a three-time bestselling author. Her books are Don't Leave Money on the Table, a negotiation guide for women leaders in male-dominated industries, Dear Resilient Leader, written for leaders who are often the only one in the room, and Navigating the Career Jungle, an early-career playbook.
Past BNEDai clients include Foot Locker, American Express, and Allstate. Her focus stays the same across every format: give mid-career professionals a concrete way to move, not just a reason to feel good.
The podcast
Winning Season has been running since December 2017, with more than 300 episodes. In February 2025, Forbes named it one of the 12 Must-Listen Leadership Podcasts for Women.
The premise is simple. Every episode hands you something you can use Monday morning. A way to negotiate. A way to be heard in the room. A way to reset when the plan falls apart. It is part framework, part candid conversation, hosted by someone who has done the work and will give you the game.
Questions, answered
Who is Jacqueline V. Twillie?
Jacqueline V. Twillie is a leadership strategist, negotiation expert, and host of the Winning Season podcast. She is a three-time bestselling author of Don't Leave Money on the Table, Dear Resilient Leader, and Navigating the Career Jungle. She has led leadership and negotiation training for more than a decade. Past BNEDai clients include Foot Locker, American Express, and Allstate. She created the L.A.T.T.E. negotiation framework, the R4 Resilient Leadership Framework, and the A.H.A. leadership method, all built to help mid-career professionals advocate for their worth.
What is the Winning Season podcast about?
Winning Season is a leadership podcast for mid-career professionals who want strategy, not just motivation. Hosted by Jacqueline V. Twillie, each episode gives you a concrete tool you can use right away: how to negotiate, how to be heard in the room, how to reset when the plan falls apart. It has run since December 2017 with more than 300 episodes. In February 2025, Forbes named it one of the 12 Must-Listen Leadership Podcasts for Women.
What frameworks did Jacqueline Twillie create?
Jacqueline Twillie created three signature frameworks taught on the Winning Season podcast and in her books. The L.A.T.T.E. framework is a five-step negotiation checklist: Look at the details, Anticipate the challenges, Think about your walk-away point, Talk it through, and Evaluate options. The R4 model covers resilience through four moves: Risk, Resilience, Reset, and Reward. The A.H.A. method covers leadership growth through Attitude, Habits, and Actions.
Is Jacqueline Twillie a bestselling author?
Yes. Jacqueline V. Twillie is a three-time bestselling author. Her books are Don't Leave Money on the Table, a negotiation guide for women leaders in male-dominated industries, Dear Resilient Leader, written for leaders who are often the only one in the room, and Navigating the Career Jungle, an early-career playbook. Her writing carries the same practical focus as her Winning Season podcast: give women a clear way to move, not just a reason to feel good.
What companies has Jacqueline Twillie trained?
Jacqueline V. Twillie has led leadership and negotiation training for more than a decade, for Fortune 500 companies, government agencies, and startups. Past BNEDai clients include Foot Locker, American Express, and Allstate. She is the host of the Winning Season podcast. Her training is built around her own frameworks, so participants leave with tools they can apply, not just ideas they will forget by Friday.