Put your brand in the room where careers get decided.
Winning Season is the Forbes-recognized leadership podcast for mid-career professionals. Since December 2017, host Jacqueline V. Twillie has handed listeners the real tools for negotiation, presence, and resilience.
Request the media kit- 317+
- Episodes, each with its own indexed page
- 2017
- On air since December 2017
- Forbes
- 12 Must-Listen Leadership Podcasts for Women, February 2025
- 86
- Named guests since 2018: CEOs, founders, executives
Who listens
Mid-career professionals. Managers, directors, VPs, and founders who are preparing for a negotiation, a promotion, or a pivot and want a plan, not a pep talk.
When Jacqueline recommends something on the show, she is recommending it to a friend.
Listener numbers and platform breakdowns come with the media kit, pulled from the platform the day you ask.
What a sponsorship includes
A host-read ad, in her voice
Jacqueline reads every ad herself as a pre-roll or mid-roll. You approve the script before it airs. No stock read, no voice talent you have never heard of.
A permanent link on the episode page
Every episode has its own page on winningseasonpod.com, and the site has 317+ of them indexed. Your link stays on the page for as long as the episode exists, so the placement keeps working after the download window closes.
Newsletter and social placement
A mention in the Resilient Leader Insder newsletter and amplification on LinkedIn and Threads when the episode drops. One sponsorship, four surfaces.
A report you can forward
Download numbers for the episodes you sponsored, pulled from the platform, plus a trackable link so your team sees the clicks on your side. Platform data, not estimates.
The fit check
Winning Season takes sponsors a mid-career professional would actually use: career and negotiation tools, leadership development, professional education, financial services, workplace software, and wellness.
Jacqueline reads every ad herself, so she only takes brands she would recommend to a friend. If your product is not a fit for this audience, you will hear that on the first call, not after the invoice.
How it works
- 01
Request the media kit
Use the form below. You get the rate card, current listener numbers, and the upcoming episode calendar in one reply.
- 02
A 15-minute fit call
We talk about what you are promoting and which episodes and topics match. If it is not a fit for the audience, Jacqueline will say so.
- 03
Pick your run, approve the script
Single episode or a multi-episode run. You see and approve the ad script before anything is recorded.
- 04
Launch and report
The episode goes live with your placement on the page, in the newsletter, and on social. The report follows once the download window closes.
Questions, answered
Who listens to Winning Season?
Mid-career professionals: managers, directors, VPs, and founders who are preparing for a negotiation, a promotion, or a pivot. They listen for a tool they can use the same week. Listener numbers and platform breakdowns come with the media kit, pulled from the platform the day you ask.
What does a Winning Season sponsorship include?
A host-read ad in Jacqueline's voice, placed as a pre-roll or mid-roll and approved by you before it airs. A permanent sponsor link on the episode page, on a site where every episode has its own indexed page. A mention in the Resilient Leader Insder newsletter. Social amplification on LinkedIn and Threads when the episode drops. Multi-episode runs are available.
How much does it cost to sponsor the podcast?
Rates depend on the format, the number of episodes, and whether the newsletter and social placements are included. Request the media kit and you will get the rate card and current listener numbers in one reply.
Can we sponsor a single episode?
Yes. Single-episode placements are available, and so are short runs across several episodes, where the audience hears the message more than once.
Which brands are a fit for Winning Season?
Brands a mid-career professional would actually use: career and negotiation tools, leadership development, professional education, financial services, workplace software, and wellness. Jacqueline reads every ad herself, so she only takes sponsors she would recommend to a friend.
How do we know the sponsorship worked?
You get the episode page link for your records, a download report for the episodes you sponsored, and a trackable link so you can see the clicks on your side. Everything is reported from the platform data, not estimates.
I want to be a guest, not a sponsor. Where do I go?
Guest pitches have their own door: the Be a Guest page. If a pitch is a fit, Jacqueline emails to set a time. The sponsor form is only for brands and partners who want to reach the audience, and it asks you to confirm that.
Request the media kit and rates.
One reply with the rate card, current listener numbers, and the upcoming episode calendar. Jacqueline answers these herself.