The Unsexy Truth About Building a Career in Fashion & New Tech That’s Changing the Landscape

The AI Wave Is Here. How Top Women Leaders Are Navigating Change

If AI has you feeling behind, overwhelmed, or like everyone else already figured it out — this episode is for you. Bella sits down with Alyson Paine, Director of Microsoft 365 Consumer Apps & Services Marketing at Microsoft, for an honest conversation about what it actually feels like to lead through the AI era in real time. After more than a decade at Microsoft building teams from the ground up, Alyson shares what it looks like to navigate one of the biggest workplace shifts of our generation — while balancing leadership, motherhood, ambition, and the very human side of change. Together, Bella and Alyson unpack: • What people are getting wrong about AI • How ambitious women can stay relevant without burning themselves out • Why storytelling and human intelligence matter more than ever • The realities of leadership inside one of the world’s largest tech companies • How work, creativity, and career growth are changing in real time This is not another “AI will replace everyone” conversation. It’s a grounded, vulnerable, and deeply honest look at how smart women are adapting, leading, and building meaningful careers through uncertainty. Perfect for anyone navigating tech, leadership, ambition, burnout, or the pressure to constantly keep up. CHAPTERS:  00:00 Director at Microsoft 1:45 Why Alyson stayed in big tech instead of going startup 6:30 How the pace of work has changed inside Microsoft 7:00 How Alyson leads her team through constant change 8:45 Why oversharing context is a leadership superpower 10:45 AI is not a future state… it's happening now 11:15 "You're probably already in the top 5%"  11:45 Using AI to outsource the mental load of motherhood 13:30 Copilot vs. Claude vs. ChatGPT  15:45 Agentic AI  17:30 Analog habits in a tech world (yes, she has a wall calendar) 18:30 Where AI is headed in SF & beyond in the next 3–5 years 20:00 Why AI creates room for more senior individual contributors 22:00 The most valuable marketing skills 26:00 Advice for women who feel behind on AI 28:30 The decision to have kids in the Bay Area 29:45 How two senior-level parents make it work week to week 31:00 Childcare costs, daycare, & the 401(k) strategy that changed everything 33:30 Lifestyle creep & not inflating your cost of living with every raise 37:00 Postpartum reality: outsourcing, sleep training, & shifting expectations 39:00 Alyson’s hardest career moment 45:45 How to Detach Self-Worth From Career Achievement

A Note From Bella

Apply here to join Bridges.  [https://www.bridgessocialclub.com/] Follow OOO by Bridges on: Instagram [https://www.instagram.com/ooobybridges/] TikTok [https://www.tiktok.com/@ooobybridges] YouTube [https://www.youtube.com/@OOObyBridges]  Follow Bella Malvini on: Instagram [https://www.instagram.com/rawrr_itsbella/] TikTok [https://www.tiktok.com/@fashionskooldropout] LinkedIn [https://www.linkedin.com/in/bellamalvini/] Comment who you want Bella to interview next!  Produced by: GOGO STUDIOZ [https://www.gogostudioz.com/]

Job Search in 2026: How to Win When the Market Is Broken

Sasha Leatherbarrow has seen your resume. She's also seen the thing that got it passed over before anyone finished reading it. As Director of Global Talent at Bansk Beauty - the PE firm behind amika, BYOMA, Ethique, and Eva NYC — Sasha has built her career on knowing exactly what separates candidates who get the call from the ones who don't. On this episode of Out of Office, she and Bella get into all of it. What actually moves the needle in beauty recruiting. Why EQ will take you further than your credentials. And how Sasha went from door-to-door sales in England to running global talent for some of the most recognizable brands in the industry. She also talks about holding down a demanding PE career, pro Solidcore coaching, and a Lululemon ambassadorship — and why she thinks work-life balance, as a concept, simply isn't real. Apply here to join Bridges.  [https://www.bridgessocialclub.com/] Follow OOO by Bridges on: Instagram [https://www.instagram.com/ooobybridges/] TikTok [https://www.tiktok.com/@ooobybridges] YouTube [https://www.youtube.com/@OOObyBridges]  Follow Bella Malvini on: Instagram [https://www.instagram.com/rawrr_itsbella/] TikTok [https://www.tiktok.com/@fashionskooldropout] LinkedIn [https://www.linkedin.com/in/bellamalvini/] Comment who you want Bella to interview next!  Produced by: GOGO STUDIOZ [https://www.gogostudioz.com/]

AMA: Career, Building Confidence & Finding Personal Identity

Bella Malvini goes solo for a full Ask Me Anything (AMA) episode. No guest, no filter, and no topics are off limits. She shares how she builds confidence from the inside out, manages her time across multiple jobs, all while still making time to learn Greek at 5 AM! This episode goes into what it actually takes to run a social club, hold down a full-time tech job, and build a podcast from scratch– all at the same time!  Questions like: Would she ever leave corporate? How can you develop personal style? And does fake it till you make it still apply today?? If you’ve ever wondered how Bella keeps it all together, and want the real answer, not the polished version, this episode will not disappoint. Apply here to join Bridges.  [https://www.bridgessocialclub.com/] Follow OOO by Bridges on: Instagram [https://www.instagram.com/ooobybridges/] TikTok [https://www.tiktok.com/@ooobybridges] YouTube [https://www.youtube.com/@OOObyBridges]  Follow Bella Malvini on: Instagram [https://www.instagram.com/rawrr_itsbella/] TikTok [https://www.tiktok.com/@fashionskooldropout] LinkedIn [https://www.linkedin.com/in/bellamalvini/] Comment who you want Bella to interview next!  Produced by: GOGO STUDIOZ [https://www.gogostudioz.com/] CHAPTERS: 00:00 Why this Episode is Unlike Any Other  1:30 How to Find Hobbies Outside of Work 4:28 Tips for Developing Your Personal Style 6:34 THE Best Way to Build Up your Confidence  8:37 How to Make the Leap from Intern → Employee  9:50 Hot Take on “Fake it Till you Make It”  11:54 How to Prioritize Financial Security & Inclusivity in All Your Work 15:26 To Leave or Not to Leave Corporate (When is the Right Time?)  17:23 Why Bella Wants to Become the Female Joe Rogan (But Better!)  19:30 Time management with ADHD across Three Jobs 21:42 What is Admin Hour & Why Do You Need One? 25:39 How to Beat Laziness Using AI

The Unsexy Truth About Building a Career in Fashion & New Tech That’s Changing the Landscape

Stephanie Doiron did not take the clean, linear path to SVP — and honestly, that’s exactly why this is interesting. She started as a seasonal employee at Old Navy, made her way through Parsons School of Design, grinded through 100-hour weeks at Saks Fifth Avenue, and eventually landed at Clare V.. After nearly a decade of building Clare V.’s digital and tech function from the ground up, she’s now stepping into SVP of Digital & Technology — which, if you know anything about fashion, is not a small feat. Bella and Stephanie get into why chasing skills over titles is actually the career hack (even though nobody wants to hear that), and what actually works behind the scenes in fashion. We also get into what fashion companies consistently get wrong about technology — and it’s probably not what you think. This episode will give you a very real understanding of why the most important work in fashion and retail is the stuff no one’s talking about. Apply here to join Bridges. Follow OOO by Bridges on: Instagram [https://www.instagram.com/ooobybridges/] TikTok [https://www.tiktok.com/@ooobybridges] YouTube [https://www.youtube.com/@OOObyBridges]  Follow Bella Malvini on: Instagram [https://www.instagram.com/rawrr_itsbella/] TikTok [https://www.tiktok.com/@fashionskooldropout] LinkedIn [https://www.linkedin.com/in/bellamalvini/] Comment who you want Bella to interview next!  Produced by: GOGO STUDIOZ [https://www.gogostudioz.com/] CHAPTERS:  00:00 Introducing Stephanie Doiron, SVP of Digital & Technology at Clare V 2:35 The Zig Zag Career Lesson: Old Navy to Parsons to Saks to Clare V 5:00 Why Skills are More Important than Titles 6:10 The MBA Debate 7:45 How to Get your Foot in The Door (Fashion Industry Edition)  10:15 The unsexy reality of working in the fashion industry 13:00 What Role Does Personal Branding Play in Landing a Fashion Job?  15:30 Fashion vs. Financial Stability: How to Think About the Tradeoff 17:25 How to Level up as a Manager 22:00 Fashion Tech is Having its Moment — What's Driving It 24:30 AI in Retail 101 30:00 Fit Predictions & the Returns Problem 32:00 How DTC Brands should Approach Innovation 35:00 Digital FAILURES: The biggest mistake brands make with digital transformation 37:15 Career Advice for Ambitious Women in Fashion & Digital Commerce