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What does it take to go from answering phones to running one of the largest convention centers in the country? In this episode, Jacqueline sits down with Joyce Leveston, president and CEO of the Javits Center in New York City, to share her blueprint for women and leadership.Joyce grew up in Cincinnati, Ohio, and moved to San Diego at 19. She watched a convention center being built and talked her way into a job there as a telephone operator. She tells the story of the bold conversation that changed her path, and how a mentor taught her to take her seat at the table. Along the way she shares what she has learned over 38 years in the industry about persistence, representation, and making room for others.
What you'll hear
Key takeawaysQuote of the episode"When you light someone else's candle, it only illuminates the room."About the guest
Joyce Leveston is the president and CEO of the Javits Center in Manhattan, where she oversees about 3,000 employees. She has worked in convention centers for 38 years, across seven states.
How do you manage over 32 AI agents to build a new business when you don't have a technical background? Welcome to Part 1 of a special Winning Season mini-pod series!
In this kickoff episode, Jacqueline Twillie pulls back the curtain on the exact mindset and strategy she uses to run a fleet of AI agents using Gumloop and Claude. Using plain English (zero tech jargon!), Jacqueline explains how her background in media transformation, sales, and executive leadership taught her to build an "AI Org Chart"—and why you should treat setting up an AI agent just like onboarding a human employee.
In This Mini-Pod, You’ll Learn:
The 2 Platforms Driving the Business: Why Jacqueline uses Gumloop and Claude Agents.
The "Clarity First" Rule: Why you must write down your business goals before touching ChatGPT or Claude so you don't waste time and tokens.
The AI Org Chart: How to map out departments and delegate tasks to agents.
Plain-English Definitions: The real difference between a basic chatbot and an end-to-end AI agent using connectors (CRMs, calendars, email).
The Onboarding Secret: How to write agent instructions so they deliver work the exact way you like to receive it.
📝 Your Homework Before Part 2:
Write down your core business goals without using AI.
Sketch out a simple organizational chart of where AI agents could sit in your workflow and why.
⏱️ Episode Breakdown:
(00:01) Introduction to the 32+ AI Agent Series & Gumloop/Claude overview
(01:28) How leadership, sales, and past tech shifts prepare you for AI
(03:20) Setting goals first: Avoiding the "generic LLM strategy" trap
(04:56) Designing your AI Org Chart (Preview of Part 2)
(06:40) What is an AI Agent? (Instructions, Connectors & Onboarding)
🔗 Resources & Links Mentioned:
Try Gumloop: Get a 2-week free trial + 20% off your first month at https://www.gumloop.com/?via=smbiz | promo code "1STAGENT"
Website & Free AI Agent Build Sessions: https://bnedai.com/agent-lab
Connect with Jacqueline on LinkedIn: Search Jacqueline Twillie and send your questions for upcoming episodes!
Jacqueline sits down with Cameron Hardesty, CEO and founder of Poppy Flowers, to talk about building a nationwide e-commerce wedding florist, raising venture capital, and the mindset shifts that helped her keep going through years of rejection. Cameron shares how curiosity, industry insight, and a steady nervous system helped her spot an overlooked market opportunity and scale a business serving 10,000 couples with 1,100 floral designers.We also get into the cultural forces that shaped both women as elder millennial founders, from girl boss era ambition to the realities of fundraising, motherhood, and entrepreneurship.
Cameron’s perspective is both practical and grounded, with a memorable framework from her coach Mo called awareness relax.Key topics
Chapters
00:00 - Cameron Hardesty and the story behind Poppy Flowers
00:42 - Founder introduction and Poppy’s scale across the wedding industry
01:23 - Southern identity, Dallas vs New Orleans, and regional personality
02:13 - The Southern woman vs Texas woman lesson Cameron learned in college
04:18 - Millennial pink, elder millennials, and cultural references that shaped a generation
05:49 - How career-first messaging from moms and the Lean In era shaped ambition
07:34 - Girl boss culture, The Hills, and postponing life decisions until later
09:23 - Venture capital tailwinds and why timing mattered for fundraising
10:40 - Building during the zero interest rate era and the 2022 bubble shift
11:41 - The hard work behind making fundraising look easy
12:18 - Starting the entrepreneurial project in 2013 and going full time in 2015
13:07 - Learning fundraising and market dynamics from the inside
13:58 - Finding the floral industry gap through curiosity and observation
15:18 - Side quests, canning, preserving, and following curiosity wherever it leads
16:18 - Why Cameron thrives in both creative and competitive work
17:08 - Poppy’s business model and the economics of wedding florals
18:52 - Serving high budget clients without forcing overspend
19:53 - Customer feedback, transparent pricing, and removing pressure
21:25 - Why referral growth and organic traffic are compounding over time
22:25 - Fundraising lows, highs, and the reality of hearing no repeatedly
23:20 - Early angel investors, friends and family, and a major floral industry backer
24:14 - Techstars Atlanta and the first priced round of $1.65 million
24:40 - What a SAFE note is and why it is founder friendly
25:51 - Series A funding and the role of a female lead investor
26:35 - Mindset, belief, and seeing opportunity that others miss
27:26 - Mo the coach and the spiritual side of founder support
28:28 - Awareness relax as a framework for staying grounded
29:49 - Using awareness relax to handle money stress and operational pressure
31:17 - The value of movement, events, dinners, and showing up in person
32:14 - Mo Technologies and the reminder that you are okay
33:32 - How to connect with Cameron and Poppy Flowers
34:07 - Supporting women founded businesses and sharing Poppy with your network
What does it take to become CEO of a four-generation family business when no one hands you the roadmap?
Melanie White, President and CEO of Hellwig Products and current Chairperson of SEMA, joins Winning Season to share how she went from cold-calling in outside sales to the C-suite by doing the job first and asking for the title later.
Melanie gets honest about the moments that shaped her: crying in her car after a brutal cold call and finding her grit on the drive home, negotiating for the president title by proving she was already doing the work, and showing up at 5 a.m. on the operations floor during COVID because that's what the business needed.We also go deep on something rarely discussed: business travel safety for women.
Melanie and I trade real stories and practical rules, from hotel floors and elevator instincts to why The Gift of Fear should be required reading for every woman on the road.
In this episode:
- Why Melanie did the job first, then negotiated the title and pay
- The follow-up habit that can carry an entire sales career
- Travel safety rules every woman in business should know
- What leading a 4th-generation, 80-year-old company actually requires
- Why your inner world shows up in your outer resultsConnect with Melanie: Hellwig Products (hellwigproducts.com) | LinkedIn linked in show notes
CHAPTERS
00:00 – Welcome: Meet Melanie White, CEO of Hellwig Products & SEMA Chairperson
01:00 – Life on the road as a busy executive and mom
03:10 – Hotel safety: first floors, motels, and the "upgraded room" she turned down
05:30 – The Gift of Fear and trusting your gut as a woman traveler
06:50 – The elevator story: exiting gracefully when your intuition speaks
09:00 – Jacqueline's 3 travel rules: hotels over Airbnbs, the door stop, ride-share location sharing
10:30 – Melanie's 3 rules: higher floors, fully charged phone, carry-on only, never land after 9pm
13:10 – From French bakery to cold calling: how the journey started
14:30 – Crying in the car after a brutal cold call — and the grit that followed
16:45 – Cold calling lessons that still apply: preparation and knowing your product
17:15 – The most underrated sales skill: follow-up (and the 7-touch rule)
21:10 – What Hellwig Products makes: sway bars, helper springs & the "no saggy bottoms" policy
22:30 – The path to CEO: do the job first, ask for the title later 24:00 – Negotiating for president: "Go ahead, tell me no"
26:20 – Why the path wasn't calculated — and why that made her more invested
28:20 – 5 a.m. on the operations floor during COVID: learning through challenge
30:20 – Lifelong learning: Traction, Who Moved My Cheese, and the Audible library
33:10 – The Susie Batiz connection: Alive OS and inner work for business leaders
36:35 – "Your inner world is reflected in your outer world"
39:20 – AI, the future of work, and why human connection can't be replaced
41:40 – Melanie's parting wisdom: sometimes we are our own biggest hurdle
43:50 – Closing: emulate excellence, eliminate excuses
Connect with Melanie
Hellwig Products (company)
SEMA (her chair role)
Most high-achieving women are taught to keep their heads down, do the work, and wait to be noticed.
Julia Rock says that mindset quietly kills careers. In this conversation, she reveals the moves that took her from working at ExxonMobil for 12 years to leading a global business, coaching more than 1,000 professionals, and writing Uncomplicated Leadership.
Jacqueline and Julia break down the moments that changed everything from learning that asking for help is a strength, not a weakness, to using self-advocacy to finally get promoted after a held-up cycle. Julia also shares how a leader at ExxonMobil told her she was not a robot and should challenge what did not make sense, a lesson that reshaped how she showed up in rooms where billions of dollars were on the line.
You’ll discover:
Julia also gets honest about the faith, timing, and surrender behind leaving a corporate paycheck, and how her TEDx talk unexpectedly took off after she decided to close one chapter and step fully into the next.If you’ve ever felt stuck, under-recognized, or overwhelmed by the pressure to prove yourself, this episode is a masterclass in leadership, clarity, and career reinvention.
Connect with Julia Rock on LinkedIn https://www.linkedin.com/in/julia-rock/ and Threadshttps://www.threads.com/@thejuliarock , or email her at [email protected].
For bulk book orders, contact [email protected].
This conversation is a faith-forward career discussion with Kelvin B Henry, whose background spans the military, Procter & Gamble, PepsiCo, ministry, and coaching. He and Jacqueline Twillie reflect on mentorship, career reinvention, layoffs, AI disruption, and the personal adversity that shaped his book Rise.Kelvin shares the framework behind Rise and how it helped him process setbacks, a cancer diagnosis, and seasons of discouragement.
The episode is especially useful for anyone navigating career transition, seeking resilience, or trying to make sense of what comes next.
Key topics
Quotes from Kelvin Henry:
Chapters
(00:00) Opening prayer and introduction of Kelvin B Henry
(01:58) Jacqueline introduces Kelvin’s background and career achievements
(03:23) Greek life, shared connections, and the long friendship between guest and host
(04:13) The mentorship story that helped shape Jacqueline’s early career
(06:57) Why Kelvin’s career took him from military service to Louisiana
(09:01) Forty years of marriage and meeting his wife at the University of Florida
(10:00) What it takes to thrive in Fortune 25 companies
(12:27) Reputation, personal brand, and the importance of resilience
(14:26) The backstory behind the RISE framework
(16:14) The childhood football setback that revealed Kelvin’s encourager identity
(17:55) How Rise became a book meant to help others recover with purpose
(22:15) Cancer diagnosis, fear, and learning to surrender the moment
(23:22) Recognize, inform, strengthen, execute: applying RISE to health challenges
(26:45) How to think about AI without panic or avoidance
(30:06) Why internal work comes before external movement
(31:19) Advice for listeners facing layoffs in a difficult job market
(34:52) Encouragement to read Rise as a group and apply the framework together
(35:41) Kelvin’s closing reminder that God still writes comebacks
RISE is available now https://amzn.to/4xpG2lSConnect with Kelvin on LinkedIn https://www.linkedin.com/in/kelvin-henry/Learn more about Kelvin's coaching services https://www.abundantlyaboveconsulting.com/about
Ashwini Balasubramanian, Vice President of R&D for Transportation and Energy Business at 3M and former Harley-Davidson leader, joins Jacqueline to discuss her debut book, Map Your Ascent, and the lived experiences that shaped it. The conversation centers on navigating change, especially through career pivots, motherhood, and moments of personal uncertainty.We discuss how to move from survival mode to thriving, why generosity matters more than transactional networking, and how vulnerability can become a leadership strength rather than a liability.
Key topics
Chapters
Chapter 1: A turning point
00:00 - Welcome, Ashwini Balasubramanian and the theme of mapping your ascent
01:04 - The car accident that changed how Ashwini viewed survival and ambition
Chapter 2: The three Ps
07:24 - The three Ps framework: personality, perspective, and presence
12:46 - Learning to stay rooted while moving through major transitions
Chapter 3: Motherhood and identity
16:04 - Motherhood, maternity clothing, and the shift from fitting in to being herself
17:16 - Pregnancy on test tracks and redesigning work around physical reality
20:27 - A manager reframes motherhood as a temporary situation, not a limitation
Chapter 4: Support and vulnerability
21:54 - How Artie’s steady support became a model for real friendship and care
25:08 - Starting a women’s resource group and turning vulnerability into action
Chapter 5: Generosity and influence
30:01 - Why generosity, not networking, is the foundation of lasting influence
33:48 - Why change rarely asks for permission and how to face career disruption
Chapter 6: Closing reflections
39:18 - The win in this season: saying yes to writing a book and helping more people
Get The Book: Map Your Ascent https://amzn.to/4zuJJZ1
Visit Ashwini's website https://mapyourascent.com/
Connect with Ashwini on LinkedIn https://www.linkedin.com/in/ashwini-balasubramanian/
Kristine Frost grew up in Pontiac, Michigan, in the years when General Motors was pulling out and the families left behind built their own support systems out of mac and cheese, popsicles, and each other. She watched her grandmother, Vienna, run a government-subsidized community while her own health was failing, showing up for refugees and immigrants day after day. That is where Kristine's philanthropy started, and you can trace a straight line from it to the morning she saw a Facebook post at 4 a.m. and decided to donate a kidney to a stranger.
In this conversation, Kristine walks us through the whole arc. A trained labor and employment attorney who never wanted a law firm, she started on the floor of a stamping plant outside Detroit and rose to become the only woman in the C-suite of a male-dominated industry. Ten months ago she stepped out of that seat, founded Shattered Glass Advisory, and started answering the question so many in our community are living right now: who am I when the title is gone?
We talk about heart-centered leadership, leading up, the non-negotiable morning ritual that anchors her, and the piece of advice most people in transition don't want to hear at first: enjoy it. Kristine is a connector to her core, and this is a conversation you'll want to sit with.
🎧 Kristine is writing a book about the emotions of transition. She's coming back for the launch.
Chapters
00:01 — Welcome & meet Kristine Frost
00:38 — Growing up a Midwesterner (and why she's really a Detroiter)
03:32 — Pontiac, Flint & GM: community built close to poverty
05:40 — Vienna: the grandmother who shaped her philanthropy
07:43 — The kidney donation story begins
10:02 — Directed vs. non-directed donation & the highly sensitized program
12:22 — Finding a match: 20 vials of blood and anonymous matchmaking
14:14 — Meeting John: December 18, 2019
17:20 — From attorney to the stamping plant floor
18:58 — What a stamping plant actually is
20:01 — Real life on the floor: leading humans, not machines
22:42 — Leading up: giving executives the yes/no
25:04 — The best leader is the best ambassador of people
25:35 — Founding Shattered Glass Advisory
28:52 — "Who am I now?" Leading yourself through transition
31:03 — The formula: non-negotiables & starting the day happy
34:15 — Wanderlust, family time & what her daughter noticed
36:05 — Live, laugh, love and D.W.Y.S.Y.W.D.E.
38:21 — Where to find Kristine & closing
Links & Resources
Connect with Kristine Frost
Mentioned in this episode
Main topics:
Chapters:00:00 - Introduction to Guerlyne Guercy and her book, Grief is a Gateway
02:29 - How tearing her ACL marked a grief point and reshaped her identity
04:10 - Lessons in resilience learned from her sports career transition
05:56 - Navigating a non-linear career path from psychology to business development
06:37 - Debunking myths about sales and emphasizing authentic connection
09:34 - The role of affirmation and self-awareness in owning your strengths
12:10 - Why Guerlyne felt compelled to write about grief and faith
15:22 - The journey of accepting and walking through personal loss
16:38 - How grief reveals character and deepens spirituality
20:24 - Understanding grief as an access point to divine comfort
24:50 - Practical tools: acceptance, thanksgiving, and intentional living
27:47 - Scriptural anchors: Psalm 63 and Psalm 100 as sources of strength
30:23 - How faith evolves through seasons of loss and growth
32:36 - The significance of personal reflection and faith journaling in healing
34:28 - Supporting others in grief within the workplace and communities
37:02 - Guerlyne’s availability for speaking engagements and workshops
37:54 - Final words: Embrace your season, seek comfort, and continue moving forward
Resources & Links:
Connect with Guerlyne Guercy:
Support and speaking engagements:
Remember, grief is not the end but a gateway to renewed strength, faith, and purpose. Embrace your season, lean into your faith, and let gratitude pave your way forward.
A room full of women builders at MIT asked ChatGPT to draw them based on everything it knew. It drew the same white man over and over. That moment sparked Erica Rooney's new book, The AI Gap, and this conversation. Erica joins Jacqueline as the first AI expert on Winning Season to break down the four gaps quietly widening between who AI was built on and who gets left behind, and the surprisingly simple mindset shift that closes them. If you have ever felt like the tech wasn't built for you, this one is for you.
KEY TAKEAWAYS
Chapters:
GUEST BIO
Erica Anderson Rooney is an executive, speaker, and community builder. A former Chief People Officer recognized as a top CHRO, she is the author of The AI Gap and Glass Ceilings and Sticky Floors, founder of HER Collective, and host of two podcasts. She helps Fortune 500 companies and ambitious women learn to use AI as a voice, not become a victim of it.
RESOURCES MENTIONED
Erica's work
Referenced in the conversation
CALL TO ACTION
Run the experiment yourself. Ask your AI to generate an image of you based on everything it knows, then tag Erica on LinkedIn with what you get. Grab The AI Gap
From the publisher's feed