Rephonic
Artwork for Winning Season
VUCA
Latte Framework
AHA Framework
Negotiation
Confidence
Resilient Leaders Program
Neuroscience
Leadership
Stanford University
R4 Framework
Meetings
Linkedin
Zerogap
Racial Wealth Gap
Authentic Leadership
Zero Gap
Tell Me More
Leadership and Management
Ventromedial Prefrontal Cortex
Motivation

Winning Season is the go-to podcast for mid-career professionals who want strategy, not just motivation. Host Jacqueline V. Twillie delivers actionable tools, negotiation frameworks, and candid conversations to help you lead with clarity, advocate for yourself, and find the win in every season. From navigating career transitions to thriving in challenging work environments, each episode is packed ... more

PublishesInfrequentlyEpisodes305Founded8 years ago
Number of ListenersCategories
BusinessCareers

Listen to this Podcast

Artwork for Winning Season

Latest Episodes

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 journe... more

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 dri... more

This episode of Winning Season features a real lesson from Jacqueline V. Twillie, originally delivered live to a group of mid-career professionals. In it, Jacqueline unpacks the moment she cracked a high-stakes global project stalemate by identifying... more

Summary

In this episode of the Winning Season podcast, host Jacqueline Twillie interviews Alair Castro, a Director of Diversity and Inclusion Strategy and Marketing at Northwestern Mutual and founder of the AC Consultancy. Alair shares her journey a... more

Key Facts

Accepts Guests
Accepts Sponsors
Contact Information
Podcast Host
Number of Listeners
Find out how many people listen to this podcast per episode and each month.

Similar Podcasts

People also subscribe to these shows.

Career Contessa
Career ContessaCareer Contessa
Ratchet & Respectable
Ratchet & RespectableDemetria L. Lucas & Studio71

Recent Guests

Suzette Yasmin Robotham
Author of Beyond Titles, Speaker, former Google talent/HR leader
Author of Beyond Titles; former Google Cloud talent/HR leader
Episode: The Real You vs. Work You: Why 61% of Us Are Hiding at Work
L. Michelle Smith
Author and businesswoman; corporate media trainer who works with executives
Episode: Call and Response: Leadership Lessons w L. Michelle Smith
Alair Castro
Director of Diversity and Inclusion Strategy and Marketing for Northwestern Mutual; Founder of AC Consultancy
Northwestern Mutual; AC Consultancy
Episode: Marketing and Money Rules for Change Makers w/ Alair Castro
Lexi Mendelson
Partnership strategist with experience from startups to Google and MasterCard
Independent/Formerly at Google, MasterCard, Royal Bank of Scotland
Episode: Building Bridges: Lexie Mendelson's Partnership Strategies
Fadjanie Cadet
Inclusion and transformation strategist; certified organizational development and DEI leader
Board member; Society for Human Resource Management; Greater Boston area
Episode: Human-Centered Leadership: Blending Data & Empathy with Fadjanie Cadet

Host

Jacqueline V. Twillie
Host of Winning Season (host) focused on negotiation, leadership, and career design.

Reviews

4.6 out of 5 stars from 41 ratings
  • Great podcast!!

    So happy to have found this podcast. Love the tips they shared. Looking forward to hearing more!

    Apple Podcasts
    5
    YBMikee
    Philippines5 years ago
  • 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.

    Apple Podcasts
    5
    AM Morgan
    United States6 years ago
  • Very helpful and stimulating

    Keep doing what you’re doing ladies!!!

    Apple Podcasts
    5
    sxvon
    United States7 years ago
  • Awesome Resource

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

    Apple Podcasts
    5
    Cmu79
    United States7 years ago
  • Excellent Podcast

    Jaqueline Twilley I am inspired by your topics and your seriousness in addressing them. As a male who supports equality for all in the workplace, you give voice to women who are not able to speak up for themselves.

    Phenomenal woman for our times!

    Apple Podcasts
    5
    #leadingfromthefront
    United States7 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners note the host's direct, no-fluff approach and supportive leadership perspective.
Guests and topics are seen as highly relevant for women in leadership and mid-career professionals.
Listeners praise practical, actionable tips they can apply immediately.
Many remark on clear frameworks like LATTE and the value of real-world guest insights.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

Working Through Uncertainty - Turning Chaos Into Your Competitive Advantage w/ Jacqueline Twillie
Q: How do I lead my team when I don't have clear answers from senior leadership?
Start with data, be transparent without passing along anxiety, use a known-unknown-next framework to structure communication, specify what is known, articulate what remains unclear, and outline one concrete action that creates progress.
Volatility vs. Vision: Grounding Yourself When Everything Changes Fast
Q: How do I stay optimistic when things keep knocking me down?
Start with data, not drama, build an anchor statement from past navigations of change, and frame your capabilities as proven skills you bring to the current situation.
The Power of "Tell Me More" - A Simple Phrase That Changes Everything
Q: How do I navigate that when people shut down or give vague answers without pushing too hard or seeming intrusive?
Rephrase first, soften the approach, and give space for thoughts; use a respectful tone and acknowledge input, then invite further detail by saying you'd love to understand more about their perspective.
Marketing and Money Rules for Change Makers w/ Alair Castro
Q: What wealth-building habit do you advocate for professionals?
Diversify income by monetizing expertise through side ventures or consulting, while continuing to grow within the primary role.
Marketing and Money Rules for Change Makers w/ Alair Castro
Q: What is one practical framework you apply to move initiatives forward?
I use a lean startup approach—build, measure, learn—deploy a minimum viable version, collect data, and iterate to avoid paralysis by analysis.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Winning Season

What is Winning Season about and what kind of topics does it cover?

A practical, strategy-first show for mid-career professionals seeking tangible tools to advance at work. Episodes center on authentic leadership, negotiation frameworks, and practical career design, often anchored by a structured method like LATTE for influencing decision-makers and securing wins. Guests span leadership, inclusion, and career strategy, with heavy emphasis on turning insights into actionable steps, whether navigating pay, advancing diversity initiatives, or building resilient mindsets. The host world-builds through real-world stories, data-backed leadership theories, and focused calls to action that tie listeners to concrete programs and resources. This combination of hands-on negotiation, leadership development, and inclusi... more

Where can I find podcast stats for Winning Season?

Rephonic provides a wide range of podcast stats for Winning Season. We scanned the web and collated all of the information that we could find in our comprehensive podcast database. See how many people listen to Winning Season and access YouTube viewership numbers, download stats, audience demographics, chart rankings, ratings, reviews and more.

How many listeners does Winning Season get?

Rephonic provides a full set of podcast information for three million podcasts, including the number of listeners. View further listenership figures for Winning Season, including podcast download numbers and subscriber numbers, so you can make better decisions about which podcasts to sponsor or be a guest on. You will need to upgrade your account to access this premium data.

What are the audience demographics for Winning Season?

Rephonic provides comprehensive predictive audience data for Winning Season, including gender skew, age, country, political leaning, income, professions, education level, and interests. You can access these listener demographics by upgrading your account.

How many subscribers and views does Winning Season have?

To see how many followers or subscribers Winning Season has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

Which podcasts are similar to Winning Season?

These podcasts share a similar audience with Winning Season:

1. Career Contessa
2. Ratchet & Respectable
3. Barron's Streetwise

How many episodes of Winning Season are there?

Winning Season launched 8 years ago and published 305 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Winning Season?

Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

Where can I see ratings and reviews for Winning Season?

Rephonic pulls ratings and reviews for Winning Season from multiple sources, including Spotify, Apple Podcasts, Castbox, and Podcast Addict.

View all the reviews in one place instead of visiting each platform individually and use this information to decide if a show is worth pitching or not.

How do I access podcast episode transcripts for Winning Season?

Rephonic provides full transcripts for episodes of Winning Season. Search within each transcript for your keywords, whether they be topics, brands or people, and figure out if it's worth pitching as a guest or sponsor. You can even set-up alerts to get notified when your keywords are mentioned.

What guests have appeared on Winning Season?

Recent guests on Winning Season include:

1. Suzette Yasmin Robotham
2. L. Michelle Smith
3. Alair Castro
4. Lexi Mendelson
5. Fadjanie Cadet

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

Find and pitch the right podcasts

We help savvy brands, marketers and PR professionals to find the right podcasts for any topic or niche. Get the data and contacts you need to pitch podcasts at scale and turn listeners into customers.
Try it free for 7 days