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#3327Winning Season60.0 / 100Get badge
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Winning Season

Hosted by A bnedAI production

★5.0on Apple Podcasts · 10 recent reviews

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.

310 episodes · publishes weekly · latest 2026-06-25 · ~23 min/episode

Rank

#3327

Substance

60.0

/ 100

Breakdown

Scored 2026-07
Updated monthly

Leadership rank

#408 of 1040

Best B2B Leadership Podcasts →

Across the index

#3327 of 6181

Substance

Top 54%

outscores 46% of the index

Why it scores where it does

Winning Season ranks #3327 on The B2B Podcast Index with a substance score of 60.0 out of 100, scored across 1 recent episode. It scores highest on guest caliber and specificity & evidence. Rooney has genuine practitioner credibility as a former Chief People Officer, an author, and someone who works with Fortune 500 companies on AI adoption, and she is not purely a podcast-circuit thought leader. However, her positioning as 'the first AI expert' on the show overstates her technical depth - she is primarily an AI-literacy advocate and community builder, which limits the ceiling on practitioner insight.

The five-dimension breakdown

Averaged across 1 recently scored episode, with cited evidence.

Insight Density

11.0 / 20

The conference anecdote about AI image generation and the explanation of why LLMs reproduce historical bias (pattern recognition on skewed training data) are genuinely illustrative, but the rest of the episode is largely promotional content for Her Collective, the guest's books, and her podcasts, with substantial filler and platitudes in the back half.

“there are more men who are CEOs with the name of John than there are women CEOs. And so when AI, which is a pattern recognition machine, looks at the data”

“men in the workplace are being encouraged to use and experiment with AI at, uh, greater rates than women are. And it doesn't sound like a big deal, but that's where the gaps start to compound”

Originality

11.0 / 20

The MIT conference demonstration is a vivid, memorable story that illustrates AI bias concretely, but the analytical framework underneath it - that AI reflects historical power imbalances in training data - is widely circulating. The 'four gaps' framing is semi-original but the episode never develops it with fresh thinking; references to Carol Dweck's growth mindset and 'be curious' add nothing new.

“AI didn't necessarily get it wrong, right? AI is not introducing bias into our world. That Part AI is accelerating everything that it's been trained on”

“in a world where people dream in black and white, I'm asking them to see it in color”

Guest Caliber

15.0 / 20

Rooney has genuine practitioner credibility as a former Chief People Officer, an author, and someone who works with Fortune 500 companies on AI adoption, and she is not purely a podcast-circuit thought leader. However, her positioning as 'the first AI expert' on the show overstates her technical depth - she is primarily an AI-literacy advocate and community builder, which limits the ceiling on practitioner insight.

“I was still very much in the work. I was a fully employed chief people officer. I was still in tech”

“I go out to Fortune 500 companies and, you know, well known brands and I help them learn how to use AI”

Specificity & Evidence

13.0 / 20

There are some concrete anchors - $684/year membership price, the 17% CFOs figure, the 'more Johns than women CEOs' statistic, the Mighty platform, 300+ podcast episodes, and a Silver Telly Award - but the four-gap framework is described without data, and the claims about Fortune 500 work and organizational AI access disparities are asserted without named examples or metrics.

“A, uh, year long membership for her collective is $684. Like literally it's one meal out for a single person a month”

“only 17% of CFOs are women, it is going to automatically identify the pattern”

Conversational Craft

10.0 / 20

The host asks mostly open, soft questions ('Can you give us an overarching view?', 'Can you tell me more about how the members interact?'), frequently inserts her own anecdotes and agreements in ways that consume time without generating insight, and never challenges a claim or probes for evidence - the conversation functions more as mutual promotion than rigorous interview.

“What I'm hearing you say is be curious”

“I love that you do point and click inside of her collective because again, we're taking away the fear”

Standout episodes

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

    2026-06-25

    60

Rank over time

First period on the Index - history builds from here.

Episodes

1 scored on substance · 60 tracked in total.

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

    2026-06-25 · 29 min

    60 / 100

What listeners say on Apple Podcasts

★★★★★
Inspired Action
I enjoy this past as a listener and guest. Jacqueline consistently shares tools for leaders empowering and inspiring them to take action to lead well.

- AM Morgan

★★★★★
Awesome Resource
In life you get what you negotiate not what you deserve. The PowerBanking Podcast is a must listen for all women leaders.

- Cmu79

Frequently asked

What is Winning Season's substance score?
Winning Season scores 60.0 out of 100 for substance and ranks #3327 on The B2B Podcast Index. That puts it ahead of 46% of the B2B podcasts we rank and #408 of 1040 in Leadership. The score reflects insight density, originality, guest caliber, specificity and conversational craft across recent episodes - not downloads.
Is Winning Season worth listening to?
Winning Season is ranked on The B2B Podcast Index with a substance score of 60.0/100. See the five-dimension breakdown above to judge whether it fits what you're after.
Who hosts Winning Season?
Winning Season is hosted by A bnedAI production.
How often does Winning Season publish?
Winning Season publishes weekly, has 310 episodes, released its most recent episode on 2026-06-25.
Which Winning Season episode should I start with?
Our highest-scoring recent episode is "You're Never Stuck: Erica Rooney on Curiosity, AI, and the Questions That Change Everything" (60/100) - a good place to start.

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Guests who've appeared

Erica Rooney

Topics this show covers

The themes that come up most across this show's episodes.

ChatGPTLarge Language Models (LLMs)AI fluencygender pay gapWomen in AIAI bias and training dataThe AI Gap (book)Her CollectiveMIT AI Powered Women's ConferenceGlass Ceilings and Sticky Floors (podcast)

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