BOSS by Ali Levitan

Hosted by Ali Levitan

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Jun 2026

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BOSS by Ali Levitan is Ali Levitan's executive interview series on LinkedIn that is now a top rated Podcast. Learn, network, and pay it forward with stories from the Head of Global Partnerships at TikTok, Head of Sales at NBCU, CMO at CVS Health, CEO at Dress for Success, CMO at JPMorgan, Chief Sustainability Officer at Verizon, Head of Global Learning at Bloomberg, and more. Ali, a seasoned media, tech, and startup executive, has been featured by Fortune Magazine, The New York Times, Bloomberg, TFQ, CES, Cynopsis Media, AWS Podcast, The Federal Reserve, Wharton Magazine and more. The BOSS audience ranges from executives to people looking for new career opportunities to students looking for inspiration. BOSS stories and access to a wide variety of seasoned leaders and founders is what Ali wished she had when she was in college. Ali is now in her 40s with 2 kids (Jake and Sophia) and still looking to her BOSS network and these clips for daily inspiration and gems of wisdom.

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June 2, 202613 min

Terry Kawaja: 37 Years of Investment Banking, 55 Years of Comedy, and the Future of AdTech & AI

🎙️ "I'm 100 years old, which is why I've seen this before."That's Terence Kawaja. Creator of the LUMAscape. Founder & CEO of LUMA Partners. 37 years in investment banking. 55 years of comedy. And still calling balls and strikes in AdTech & Media better than anyone.If you've ever used a LUMAscape in a presentation, you already know his work. 24 million views. Published in The Wall Street Journal. Started as an internal tool he built to understand how the ecosystem actually worked.We have over 100 mutual connections so I know many of you already know Terry. Possible's Christian Muche officially introduced us recently but it's crazy that we have crossed paths for so long (and I even started at Salomon Smith Barney right after Terry had left after the AOL Time Warner merger - my interviewers worked on that merger too!)On BOSS this week, Terry dropped some real talk on AI in advertising:💡 "Creating agents is easy. Everyone's doing it." 💡 "Efficiency is a 10% improvement. Effectiveness is a 10x delta." 💡 First wave of AI in ad tech = workflow. The real differentiator? Decisioning.We also talked about: → Why he originally refused to do an AI LUMAscape and what changed his mind → How he separates signal from noise in a fragmented ecosystem → Why 70% of M&A advisory is actually psychology → His advice to his 20 year old self: "Trust your views"🎬 Full video + podcast link in comments 👇Who's someone you want me to interview next on BOSS? Drop their name below ⬇️

April 7, 202612 min

Every day feels like a shift in what's POSSIBLE - BOSS is back with Possible's Co-Founder, Christian Muche

Every week right now feels like a shift in what’s possible. Not even every week..every day. And that’s why Christian Muche, Founder of POSSIBLE is back on BOSS to talk about one of the most important industry events Yes, I believe we are living through one of the biggest technological shifts in human history with AI and agents accelerating literally every day what is possible. You should have FOMO if you’re not going. Seriously. And if you are going… you’ll want to watch this to learn how to actually win the week. It’s also crazy to think that almost one year ago, I went to POSSIBLE as Ali, Creator and Host of BOSS after just accepting (but not starting) at AWS… This year? I’m heading back as Ali, Amazon Web Services, and Host of BOSS First time in that seat too. Completely different lens. We’re walking into Miami at a moment where: → AI isn’t just a topic… it’s infrastructure → The real question is what actually sticks vs. what’s just noise → And one of the biggest constraints right now isn’t budget… it’s time and attention I asked Christian a simple but big question: What actually matters this year? Because let’s be honest Everyone shows up with packed calendars… But it’s usually a few conversations that define the entire week. A few things he said that really stuck with me: → “Every day feels different… you wake up and something changed.” → “The biggest ask isn’t budget. It’s time.” → “We’re still young and flexible enough to do this better than the established events.” And then we got tactical… How do you actually win the week at POSSIBLE? → Don’t just go to keynotes—find the smaller rooms and real conversations → Don’t over-plan—leave space for the unexpected moments → Don’t show up solo—the companies that win show up as teams and divide the room → And don’t just attend—be part of it Because the reality is— The deals, partnerships, and relationships that matter? They’re not happening on stage. They’re happening: → in the coffee line → at a curated exec dinner or breakfast → in between meetings → in the moments you didn’t plan for That’s why people keep coming back. That’s why this event is growing. And that’s why I’ll be there again this year. Back at POSSIBLE. Seeing it through a completely different lens. And I have a feeling the conversations happening in Miami this year are going to shape what comes next for all of us. If you’re in tech, media, advertising, adtech Watch this before you land. Real question: What’s your strategy walking into POSSIBLE this year? 👇 Curious how people are thinking about it. Follow me, Ali Levitan, for more BOSS executive interviews, agentic AI insights, and the real talk on work and life as Jake and Sophia's mom.

March 31, 202612 min

Breaking the Rules of Leadership with The Female Quotient's CEO & Founder, Shelley Zalis

I’ve known Shelley Zalis, Founder & CEO of The Female Quotient (TFQ), for a long time now…10+ times at CES together (including one where I was pregnant walking the floor 😅), Advertising Weeks, Possibles, AI events, airport run-ins. And every time we talk, I leave thinking differently about leadership, community, and honestly… how much of our industry needs to be redesigned.I’m really excited to share this new BOSS episode with Shelley, as it's a long time in the making.And it's perfect timing as we’ll both be back at POSSIBLE this year in Miami in April… and you already know I’ll be spending time in the TFQ Lounge.If you’ve been, you know.That’s where the real conversations happen.That's where I know I will run into industry friends old and new.Within the first couple of minutes of the interview, Shelley said:“I never want to look back and say shoulda, woulda, could have.”“I’m a chief troublemaker… I break every rule that makes no sense.”“We don’t get anywhere by just sitting around.”That’s the energy.She didn’t just build a company…She built a global community of millions of people showing up, connecting, and supporting each other across industries.That’s not easy to do.But she’s done it with her team.We also got into what’s happening right now:→ Why we’re moving from audience → community → Why community isn’t just a buzzword, it’s how trust, relationships, and business actually happen → And why AI is an opportunity, opportunity, opportunity, if you lean inAnd honestly—this is what I keep coming back to:So much of what’s shaped my career didn’t come from a meeting or a title.It came from people.From communities.From moments where you show up, connect, and something real happens.That’s why spaces like TFQ matter.Also, very on brand—30 seconds into the interview she flipped it and started asking me questions 😂If you’re building, leading, navigating your next move or just thinking about what kind of leader you want to be—You’ll want to watch this one.If you’re going to POSSIBLE—are you stopping by the TFQ Lounge?👇 And bigger question…What’s one “rule” in our industry that just doesn’t make sense anymore?Let’s rewrite a few of them.Follow me, Ali Levitan, for more BOSS executive interviews, agentic AI insights, and the real talk on work and life as Jake and Sophia's mom.

February 12, 202611 min

BOSS with Steven Wolfe Pereira, CEO Alpha | No One Wants to Look Dumb About AI

We have 640+ mutual LinkedIn connections. But I didn’t actually meet Steven Wolfe Pereira ⚡️ in real life until I stopped him at Starbucks at CES ☕️ Very 2026. Shortly after, I had him as a guest on BOSS, and this conversation stuck with me. I'm excited to share it with all of you. Steven started his career at Blackstone in 1994. Jumped to Akamai in 1999 when everyone thought it was crazy. Built across finance, infrastructure, data, media, tech. Pattern recognition across multiple waves. And now? He says we all need to have a “wake the hell up” moment. Because we are in the agentic era. Not AI as content fluff. Not AI as a buzzword. AI agents inside enterprises. Working alongside people. Talking to each other. Making decisions. But here’s the shift most leaders are underestimating: They care about: • Your data • Your structure • Your governance • Your infrastructure This is no longer just a marketing conversation. It’s a boardroom conversation. And Steven said something I think a lot of executives quietly feel: “No one wants to look dumb in front of their peers when it comes to AI.” But staying quiet doesn’t slow this down It just widens the gap. The first inning was curiosity. The second inning is capability. 👇 So I’ll ask it directly: Are you building? Or are you hoping this is still just hype? Watch the full BOSS episode with Steven,CEO Alpha, to hear his story and our conversation. 🔥 And follow me, Ali Levitan, for more BOSS executive interviews, industry insights… and yes, work & life as Jake & Sophia's mom

December 19, 202513 min

BOSS with my boss, Tim Barnes, GM AWS for Advertising & Marketing

On BOSS this week, I interviewed my boss, Tim Barnes, at Amazon Web Services (AWS).We talked AdTech, Agentic AI, CES, and what actually matters as we head into 2026."I think the next sea change in AdTech is going to be an interoperability of AdTech based on agents." - TimTim leads the Advertising & Marketing vertical at AWS, and he has built his career through multiple cycles of this industry, from early CRM and AdTech days to AT&T/Xandr and now AWS.What stood out most in this conversation wasn’t hype."I think everyone knows who's in this industry; this is an industry driven by annual buzzwords." - TimIt was clarity.On agentic AI, Tim said what a lot of people are thinking:This industry loves buzzwords.Some move the needle. Some don’t.This one feels different.Why? Listen to find out as 2026 is shaping up to be a pivotal year.We also talked CES!"The relationships we enjoy in this industry are priceless and very easy to obtain at first, but difficult to nurture and maintain long term." TimCES is about...reconnecting with old colleagues.Understanding real customer business challenges.C-suite conversations that are unique to CES & Cannes, and how relationships shape what comes next.That same thinking is what led us to bring industry leaders together at AWS re:Invent for the launch of the AWS AdTech Executive Advisory Forum Roundtable, to build community, deepen relationships, and have candid conversations on shaping the future of AdTech.Listen all the way through if you’re curious why Tim hired me.If this episode resonated, like it, share it, and comment below.And follow me, Ali Levitan, for more BOSS executive interviews, AdTech + AI insights, and the real talk on work and life as Jake and Sophia’s mom.Happy Holidays, and see you all in Vegas next year!

November 19, 202512 min

AdTech, Agentic AI, and Saying What Others Won’t - BOSS with Ari Paparo

“I call myself an AdTech influencer… which is a little bit of a joke, but it's also true.” That’s how Ari Paparo kicked off our BOSS interview, and the insights that followed make it clear why this conversation is worth your time.🎙 AdTech, Agentic AI, and Saying What Others Won’t — with Ari Paparo is now live.In this BOSS episode, we covered: 📌 How performance is reshaping the narrative across marketing and media 📌 The three waves of AI, from workflow automation to system-to-system efficiency to potential transaction-level execution 📌 What clear communication, real strategy, and product leadership look like in today’s environment 📌 Why technical fluency matters more than ever — across roles and levels 📌 How Marketecture Media is evolving as a platform for honest, smart, and cross-functional conversation in AdTechWe also talked about career advice, product thinking, and the importance of staying curious, from SQL and Python to AI-powered tools that can 10x how we work.If you're in the marketing, media, or advertising ecosystem, this one's for you.🎧 Watch or listen to the episode and let me know what resonated. Tag someone who should be part of this conversation, or who you want to see on BOSS next.And follow me, Ali Levitan, for more BOSS executive interview

October 17, 202511 min

BOSS with Marie Han Silloway, Gartner's Executive Partner on Risk, Reward, and AI

What would happen if you said yes to something that scared you at work and in life? That question changed everything for Marie Han Silloway, Executive Partner at Gartner, and this week’s guest on BOSS.This week on BOSS, I sat down with Marie, a global marketing leader whose career has spanned Coca-Cola, Starbucks, Estée Lauder, Godiva, and Subway. Her story hits every note on courage, clarity, and growth.Marie said yes to moving halfway across the world to China with a newborn. She said yes to leading through uncertainty and cultural complexity. And she said yes again when the world shifted toward Agentic AI and nonstop transformation.🎯 Her biggest insight:“Resilience isn’t perseverance. It’s adaptability. It’s testing, learning, and resetting without losing momentum.”We talked about: 💡 How calm and clarity are the ultimate leadership superpowers 🤝 Why asking better questions beats having all the answers ⚡ The real ways CMOs and agencies are using Agentic AI to move faster, smarter, and more creatively 🚨 Why the risk of doing nothing with AI is now higher than everIf you’ve ever hesitated to take a leap or wondered how to keep your edge when the rules keep changing, this one’s for you.🎙️ Watch the full episode of BOSS x Marie Han Silloway below 👇 Then tell me in the comments: What’s one thing you’ve said “yes” to that scared you and changed everything?

September 3, 202513 min

BOSS with Peter Naylor, Advisor, Investor, & Former Netflix, Snap, Hulu, NBCU Revenue Leader as we talk AI & The Future

"I think there is a huge risk, and it’s all going to continue to evolve faster than anybody is ready for." Peter Naylor, Advisor, Investor, and Former Netflix, Snap, Hulu, NBCU Revenue leader, joined me on BOSS to unpack the future.Curious what we’re talking about?🎙️ In just 13 minutes, we covered:→ What Agentic AI means for media & marketing→ Why most execs need to rethink how they’re learning→ What leaders should stop doing, and what they must start⚡️ Favorite Peter Naylor moments:🧠 “You better be studying AI every day. And there's no reason not to be an expert on your customer's business."🧠 “Be a good person. Be nice. This business is full of relationships.”🧠 “Could your product become a feature in someone else’s AI platform?”💬 Watch the episode.💬 Share it with your team.💬 Then tell me: What’s the smartest question YOU heard or read this week?👇Tag the exec, podcast, or newsletter that’s making you smarter right now.And of course…🎧 BOSS: My Executive Interview Series & Podcast — quick hits with 100+ leaders to help others learn, network, and pay it forward.And follow me, Ali Levitan, for more BOSS executive interviews, AI & AdTech insights, and the real talk on work and life as Jake and Sophia's mom during back to school Week 1!

July 10, 202513 min

BOSS with Hootsuite's Social Media Strategy Lead, Trish Riswick | It's ok to feel the cringe

Unpopular truth? The best companies aren’t just building great products, They’re building thought leaders from within.🔥 Empowering employees to find their voice 🔥 Encouraging the C-Suite to actually show up online 🔥 Using social as a business growth engine, not just a branding toolThat’s why this BOSS interview is a must-watch.🎙️ Meet @Trish Riswick, team lead of social marketing at Hootsuite, and one of the sharpest voices out there on social strategy, employee advocacy, and the power of showing up, cringe and all.We talked about: 📍 The real reason some companies win on social 📍 Why leaders should act like creators (hint: your people > your logo) 📍 How to build internal influence, even if you’re not the CEO 📍 And why it’s totally OK to feel cringey when you start posting (That’s how every thought leader begins.)My favorite line from Trish? 👉 "Your world, your story, your people — that’s what sets you apart. People follow people, not brands."If you’re in marketing, sales, or social, or you’re leading a team and wondering how to activate your people, or if you're the CEO, watch this one.🚀 This is the playbook.🎧 Watch & listen to BOSS: my executive interview series on LinkedIn & podcast where I interview 100+ top leaders to help others learn, network, and pay it forward. New episodes dropping soon!👇 Who’s your favorite brand leader to follow on LinkedIn? Tag them. Let’s build each other up.

May 27, 202511 min

BOSS with Soyoung Kang, CMO eos!

“Why?” and “Why not?”If you’ve ever been in a meeting with Soyoung Kang, CMO eos Products, those are the two questions you’ll hear most.That curiosity has powered her unconventional career:📍 From management consulting📍 To retail merchandising📍 To building one of the most beloved beauty brands in the worldIn this new BOSS interview, we finally got to have the conversation we’ve been meaning to have for years, after connecting on social and running into each other at events.What we covered:🔥 Her 3-part career journey, and how each stage built different leadership skills🔥 The Gen Alpha insight that’s driving eos’ newest campaign🔥 Why asking “Why?” is often the most powerful move in the room🔥 What happened when eos actually listened to a product complaint (spoiler: it went viral)🔥 Her take on the “thinker vs. doer” debate, and why that binary misses the pointAnd maybe my favorite moment: 💬 “The most impactful marketing doesn’t always come from splashy headlines. It comes from the small, intentional decisions we make every day.”This episode is packed with takeaways for everyone and anyone who’s ever felt like the non-linear career path might just be the best one.👇 Drop a comment with your favorite takeaway or guest rec! 👉 ❤️ Follow me, Ali Levitan, for more BOSS content, Marketing & AdTech insights, new job highlights, and, of course, all things AI.