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The Seat
Kym Insana, Founder & President – AlwaysOn Digital
Episode Summary:
In this episode of The Seat, Ray Erickson sits down with Kym Insana, Founder and President of AlwaysOn Digital, for a candid conversation about leadership, reinvention, and building a business on your own terms. Kym shares her path from an after-school job in radio to rising through the early days of digital advertising and ad tech leadership before launching AlwaysOn Digital in 2016. As the company celebrates its 10-year anniversary, Kym reflects on the challenges of transitioning from corporate executive to founder, navigating acquisitions and layoffs, balancing career and motherhood, and building a people-first company rooted in trust, flexibility, and service.
The conversation explores mentorship, leadership philosophy, hiring, entrepreneurship, resilience, and what it really takes to earn, and grow, into your seat.
Chapters:
00:00 — Leadership Starts with Trust
00:40 — Welcome to The Seat
02:48 — From Radio Intern to Advertising Career
07:15 — Relationships, Mentorship & Early Career Lessons
09:24 — Growing from Seller to Leader
12:09 — Acquisitions, Uncertainty & Career Resilience
16:31 — Motherhood, Burnout & Searching for Flexibility
21:02 — The Leap: Launching AlwaysOn Digital
29:02 — Building AlwaysOn’s People-First Model
40:13 — Leadership Advice, Hiring & Earning Your Seat
Key Themes:
- Leadership through trust and empowerment
- The importance of mentorship early in your career
- Relationship-building as a long-term career advantage
- Navigating acquisitions and uncertainty
- The emotional reality of layoffs and reinvention
- Transitioning from executive to founder
- Building a business around flexibility and work-life balance
- Supporting working mothers in media and advertising
- Hiring for positivity, trust, and accountability
- Defining success beyond revenue and title
Keywords:
Kym Insana, AlwaysOn Digital, Ray Erickson, The Seat Podcast, leadership, entrepreneurship, founder story, women-owned business, digital advertising, media, ad tech, mentorship, career growth, sales leadership, work-life balance, working mothers, programmatic advertising, media agency, business growth, leadership advice, startup journey
Kym's Bio:
Kym is a multi-million dollar business owner, digital marketing expert, and founder of AlwaysOn Digital, a women-owned agency helping brands like the U.S. Air Force, Enfamil, and Johnston & Murphy scale through impactful campaigns. With over 20 years of experience, Kym left her demanding NYC advertising career to build a company that offers flexibility and balance, values she champions as a wife and mother of four. AlwaysOn Digital thrives by empowering talented working parents to blend career success with family life. A sought-after speaker, Kym has shared her journey and expertise on national stages, including The Big in San Francisco and iMedia Brand Summit.
Ray's Bio:
Ray Erickson is the host of The Seat, a podcast featuring 1:1 conversations with revenue leaders across media, marketing, and advertising, unpacking the early days, mentors, setbacks, and pivotal moments that shaped how they lead today. Ray is a sales leader with over 20 years in ad-tech, CTV, and digital media, He created The Seat to sharpen his own leadership edge while paying it forward to the next generation of aspiring sales leaders.
Social Links:
Instagram: @theseat.pod
TikTok: @theseat.pod
LinkedIn: The Seat Podcast (LinkedIn Page)
Host: Ray Erickson (LinkedIn)
Website: www.theseatpodcast.com
Listen:
Apple Podcasts / Spotify / iHeart / Pandora / Acast / YouTube
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14. Ethan Heftman, CRO - New Tradition
52:15||Season 2, Ep. 14Episode Summary: In this episode of The Seat, Ray Erickson sits down with Ethan Heftman, Chief Revenue Officer at New Tradition, for a conversation about leadership evolution, career reinvention, and navigating the constant change within modern media. Ethan shares how a political science major looking for rent money in New York unexpectedly launched a 25+ year career spanning agency investment, advanced advertising, streaming, and now out-of-home media. From carrying a sales list at A+E Networks to leading revenue organizations at Ampersand and New Tradition, Ethan opens up about the lessons that shaped his leadership style, including the importance of listening, humility, self-awareness, relationships, and embracing discomfort. The conversation also explores the future of out-of-home advertising, the power of real-world media experiences, and why human connection still matters more than ever in an increasingly automated world.Chapters: 00:00 — Leadership Lessons & The Golden Rule 01:00 — Introducing Ethan Heftman & New Tradition 03:00 — From Political Science Major to Media Career 08:45 — The Smuckers Account & Learning to Embrace Discomfort 14:00 — Why Relationships Create Opportunity 16:00 — The Pivot from Agency Side to Sales Side 20:30 — Ego, Self-Awareness & Carrying a Sales List 24:00 — Building Advanced Advertising at A+E Networks 33:00 — Leadership Evolution & Becoming a CRO 36:00 — Why Ethan Joined New Tradition & The Future of OOH 46:00 — Advice for Future Revenue Leaders & Lightning RoundThemes: Career reinvention and growth through discomfortLeadership evolution and self-awarenessThe importance of listening in sales and leadershipRelationships as the foundation of career growthMoving from agency leadership to sales leadershipBuilding emerging media businesses before market adoptionGratitude versus expectationsScaling teams and revenue organizationsThe future of out-of-home advertisingHuman connection in an increasingly automated worldKeywords: Ethan Heftman, New Tradition, Out of Home, OOH, DOOH, media leadership, CRO, chief revenue officer, advertising sales, advanced advertising, A+E Networks, Ampersand, media careers, sales leadership, leadership podcast, revenue leadership, agency side, ad sales, career pivots, mentorship, media industry, leadership development, streaming, programmatic advertising, marketing leadership, The Seat Podcast, Ray EricksonEthan's Bio:Ethan Heftman is Chief Revenue Officer at New Tradition, where he leads sales, marketing, and go-to-market strategy for one of the fastest-growing out-of-home media companies in the United States. With more than 25 years of experience across the advertising and media landscape, Ethan has built a career around scaling revenue organizations, launching innovative media solutions, and helping clients drive meaningful business outcomes.Prior to New Tradition, Ethan held senior leadership roles at Ampersand and A+E Networks, where he helped build advanced advertising and multiscreen video businesses during some of the industry’s biggest transformational shifts. His background spans sales leadership, product development, marketing strategy, and advanced measurement, giving him a unique perspective on the evolving media ecosystem and the future of advertising.Ray's Bio: Ray Erickson is the host of The Seat, a podcast featuring 1:1 conversations with revenue leaders across media, marketing, and advertising, unpacking the early days, mentors, setbacks, and pivotal moments that shaped how they lead today. Ray is a sales leader with over 20 years in ad-tech, CTV, and digital media, He created The Seat to sharpen his own leadership edge while paying it forward to the next generation of aspiring sales leaders.Social Links:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast (LinkedIn Page)Host: Ray Erickson (LinkedIn)Website: www.theseatpodcast.comListen:Apple Podcasts / Spotify / iHeart / Pandora / Acast / YouTube
12. Sean Galligan, CRO - Kochava
50:45||Season 2, Ep. 12Episode Summary: Sean Galligan, CRO of Kochava, joins The Seat to break down a 20+ year career built across telecom, mobile, programmatic, CTV, and now AI. From knocking on doors doing 50 cold calls a day at MCI, to taking pay cuts during near-shutdown moments at Flurry, to leading global revenue organizations, Sean shares the leadership lessons that shaped how he operates today. This conversation focuses on what it really takes to lead through uncertainty...building resilient teams, adapting through industry shifts, hiring “athletes,” and developing a growth mindset in the age of AI.Chapters: 00:00 – Intro & Welcome02:30 – Telecom Roots & Cold Calling Foundation08:50 – Startup Life: Growth, Failure & Early Lessons15:45 – Flurry: Pivot, Survival & Breakthrough20:10 – Scaling Teams: Hiring & Leadership Development25:30 – Leading Through Industry Shifts28:30 – Leadership in Uncertainty & Change31:30 – Frameworks for Driving Performance35:30 – Kochava, Growth & AI Opportunity42:05 – Leadership Philosophy & Path to CRThemes: Leadership development over timeResilience and navigating setbacksMentorship and career ownershipHiring and team building philosophyAdapting through industry/platform shiftsGrowth mindset and continuous learningAI and the future of go-to-marketCustomer-centric leadershipStructure, process, and executionCollaboration and cross-functional leadershipKeywords: Sean Galligan, Kochava, CRO, adtech, CTV, programmatic advertising, leadership podcast, sales leadership, revenue leadership, startup growth, Flurry, Yahoo, AI in advertising, agentic AI, go to market strategy, sales management, mentorship, career growth, media industry, digital advertisingSean's Bio: Sean Galligan is Chief Revenue Officer at Kochava, where he leads global go-to-market strategy across sales, partnerships, customer success, and marketing. With more than 20 years of experience across startups and global technology companies, Sean has built and scaled multiple businesses from $0 to $100M+ and led large, cross-functional teams spanning sales, product, and operations. His career has spanned telecom, mobile, programmatic, CTV, and now AI, giving him a unique perspective on how to lead through constant industry change and drive growth at scale.Ray's Bio: Ray Erickson is the host of The Seat, a podcast featuring 1:1 conversations with revenue leaders across media, marketing, and advertising, unpacking the early days, mentors, setbacks, and pivotal moments that shaped how they lead today. Ray is a sales leader with over 20 years in ad-tech, CTV, and digital media, He created The Seat to sharpen his own leadership edge while paying it forward to the next generation of aspiring sales leaders.Social Links:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast (LinkedIn Page)Host: Ray Erickson (LinkedIn)Listen:Apple Podcasts / Spotify / iHeart / Pandora / Acast / YouTube
11. Brian Danzis, Global Chief Revenue Officer - Seedtag
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10. Lindsey Kintner, Global Head of Sales - Foursquare
47:48||Season 2, Ep. 10Episode Summary: In this episode of The Seat, Ray Erickson sits down 1:1 with Lindsey Kintner, Global Head of Sales at Foursquare. With more than 20 years across AOL, MySpace, The Wall Street Journal, Condé Nast, Fortune, and now Foursquare, Lindsey shares the key moments that shaped her path from account management into leading global revenue teams. The conversation dives into the importance of storytelling in a data-driven world, what great sales leadership looks like today, and how to identify and develop top talent.Lindsey also shares her leadership mindset, from “Be the Bison” and facing challenges head-on, to the importance of zooming out to prioritize and act. Timely to this conversation, she’s heading into Foursquare’s global Sales Kickoff this week, applying many of these principles in real time, with inspiration from The Art of Gathering. A practical, honest look at what it takes to grow, lead, and earn your seat.Chapters:02:47 – Growing up in North Carolina, UNC Chapel Hill, and the road to DC03:30 – The pivot from physical therapy to sports marketing at GW and the Women's US Soccer Association06:14 – AOL, managing NFL, NBA, and NASCAR partnerships in the early internet era09:56 – Fox Interactive Media and MySpace13:45 – The decision to carry a bag19:03 – A decade at Fortune31:10 – Engineer your epiphany35:44 – Joining Foursquare and the company solves for44:00 – Advice for aspiring sales leaders: zoom out, be the bison, ruthlessly prioritize46:37 – Lightning Round: The Art of Gathering, F1, Spotify, New York, and 'Be brave'Themes: • The unconventional path: From sports science to digital media leadership• Early internet and AO: The best training ground you never saw coming• Reading the room: Knowing when to pivot and when to stay• Leading through industry contraction: Keeping teams focused externally when everything is turbulent internally• Engineer your epiphany: How great mentors guide discovery without giving the answer• Be the Bison: Heading into the storm as a leadership and cultural philosophy• Zoom out: Ruthless prioritization as a daily leadership practice• Foursquare's evolution: From check-ins to a full-stack measurement and outcomes platformKey Words: Lindsey Kintner, Foursquare, sales leadership, global head of sales, ad tech, digital media, location data, measurement, contextual advertising, data-driven marketing, outcomes, programmatic, premium publishing, career pivot, leadership development, team building, hiring philosophy, talent development, women in leadership, sales career advice, adaptability, be the bison, engineer your epiphany, intrinsic motivation, curiosity, mentorship, geolocation media industry, career growth, leadership podcastLindsey's Bio: Lindsey Robb Kintner is the Global Head of Sales at Foursquare, leading the company's go-to-market organization across revenue growth and monetization. With 20+ years in digital media and advertising, she has held leadership roles at Fortune, Condé Nast, Time Inc., Meredith, Yahoo, and News Corp, beginning her career managing sports partnerships at AOL. Originally from North Carolina, Lindsey holds degrees from UNC Chapel Hill and George Washington University and lives in Riverside, Connecticut.Ray's Bio: Ray Erickson is the host of The Seat, a podcast featuring 1:1 conversations with revenue leaders across media, marketing, and advertising, unpacking the early days, mentors, setbacks, and pivotal moments that shaped how they lead today. Ray is a sales leader with over 20 years in ad-tech, CTV, and digital media, and currently serves as the first NYC sales hire at Intuit MediaLabs, where he is building out the company's east coast presence. He created The Seat to sharpen his own leadership edge while paying it forward to the next generation of aspiring sales leaders.Social Links:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast (LinkedIn Page)Host: Ray Erickson (LinkedIn)Listen:Apple Podcasts / Spotify / iHeart / SiriusXM / Acast
9. Chad Hickey, Founder & CEO - Givsly
44:04||Season 2, Ep. 9Summary/Episode Description: In this episode of The Seat, Ray Erickson sits down with Chad Hickey, Founder and CEO of Givsly, for an unfiltered conversation about the career moments, mindset shifts, and late-night decisions that led him to build one of the most innovative companies in advertising today. He opens up about imposter syndrome at the executive level, what turning 40 unlocked in him, and how a volunteer dinner with the CMO of McDonald's China sparked the idea that became Givsly. Chad also shares his will-versus-skill hiring philosophy, what great sales leaders are getting wrong in today's environment, and why the rise of AI is the single biggest opportunity for hungry young professionals to prove their value. Whether you're an aspiring leader, a current executive, or a founder figuring it out in real time, this one's for you.Key Themes: Will vs. skill building teams on hunger, not pedigreeScaling from startup scrappiness to $100M what year one of building really looks likeImposter syndrome at the CRO and CEO level, and why over-preparation is the antidoteThe founder's turning pointGivsly's originValues alignment as commerce behavior, not cause marketingLeading through uncertainty, the pandemic, pivoting products, and planning for every scenarioMentorship without titles, how great leaders shape others informallyAI, human value, and why this is the moment for young sales professionals to double downChapters: 02:16 – University of Arkansas, journalism, and selling print ads in college03:49 – What digital advertising looked like in its infancy05:11 – Seven years at AJC, from $18 restaurant classifieds to leading digital sales09:36 – Doing the job before you have the title10:51 – Building the national team and scaling to $100M18:54 – The CRO seat: P&L lessons, imposter syndrome, and learning from the inside22:09 – Placed, the Snap acquisition, Italy, and the decision to found Givsly33:25 – Mentorship, Andy Daidone, and knowing the details and the data36:36 – Advice for aspiring sales leaders: run it like your own business41:09 – Lightning RoundKeywords: Chad Hickey, Givsly, values-based advertising, purpose-driven marketing, founder story, entrepreneurship, CRO, Chief Revenue Officer, ad tech, mobile advertising, location data, GroundTruth, xAd, Placed, Snap acquisition, sales leadership, revenue leadership, imposter syndrome, will vs skill, startup founder, media advertising, nonprofit, social impact, sales career advice, leadership development, mentorship, building a sales team, advertising industry, performance marketing, brand values, cause marketing, commerce behavior, podcast, career journeyChad's Bio: Chad Hickey is the Founder and CEO of Givsly, the leading values-based advertising and marketing platform. Since 2019, Givsly has contributed over $4 million to 500+ nonprofits while driving measurable results for hundreds of brand and agency partners, earning recognition in Fast Company's World Changing Ideas Awards. Prior to founding Givsly, Chad spent 17 years leading revenue teams in mobile and location advertising, including scaling GroundTruth to over $100 million in annual revenue and leading sales at Placed through its acquisition by Snap.Ray's Bio: Ray Erickson is the host of The Seat, a podcast featuring 1:1 conversations with revenue leaders across media, marketing, and advertising, unpacking the early days, mentors, setbacks, and pivotal moments that shaped how they lead today. Ray is a sales leader with over 20 years in ad-tech, CTV, and digital media, and currently serves as the first NYC sales hire at Intuit MediaLabs, where he is building out the company's east coast presence. He created The Seat to sharpen his own leadership edge while paying it forward to the next generation of aspiring sales leaders.Social Links:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast (LinkedIn Page)Host: Ray Erickson (LinkedIn)Listen:Apple Podcasts / Spotify / iHeart / SiriusXM / Acast
8. Sara Badler, Chief Advertising Officer, North America - The Guardian
43:34||Season 2, Ep. 8Episode Summary: Sara Badler, Chief Advertising Officer, North America, at The Guardian, joins The Seat to discuss her journey from early programmatic pioneer to C-suite leader at one of the world’s most respected news organizations. From building global teams at The New York Times and Dotdash Meredith to learning tough lessons at Morning Brew, Sara shares why outcomes matter more than titles and how patience, scrappiness, and ego-free leadership define modern executives.Themes: Early days of programmatic advertisingBuilding global programmatic at The New York TimesScaling revenue at Dotdash MeredithLessons from Morning BrewLeadership evolution from IC to executiveThe 150% Rule for career growthConfidence vs. ego in leadershipCross-functional collaboration as a differentiatorPremium publishing in a changing media landscapeMentorship and building a loyal benchChapters: 00:00 – Intro01:43 – Growing Up in St. Louis & Moving to Asia04:24 – Discovering Ad Tech in Shanghai07:45 – Early Programmatic at Forbes10:33 – Leadership Begins at Hearst & The New York Times15:55 – Scaling at Dotdash & The 150% Rule19:25 – Imposter Syndrome & Corporate Politics23:56 – Why The Guardian32:29 – Red Flags, Hiring & Cross-Functional Growth40:00 – Morning Brew Lessons & Lightning RoundKeywordsSara Badler, The Guardian, programmatic advertising, premium publishing, media leadership, chief advertising officer, ad tech, digital media, sales leadership, revenue growth, mentorship, women in leadership, programmatic sales, publishing industry, executive leadership, cross-functional collaborationSara's bio:Sara Badler is Chief Advertising Officer, North America at The Guardian. She oversees advertising, marketing, operations, and global programmatic for one of the world’s most respected independent news organizations. Previously, she served as Chief Commercial Officer at Morning Brew and spent six years at Dotdash Meredith, where she rose to Chief Revenue Officer, Enterprise Advertising & Partnerships. Earlier in her career, Sara helped build programmatic at The New York Times and held business development roles at Hearst and Forbes. She also began her career internationally in Japan and China and serves on advisory boards including AdExchanger and Adelaide Metrics.Ray's Bio: Ray Erickson is the host of The Seat, a podcast featuring 1:1 conversations with revenue leaders across media, marketing, and advertising, unpacking the early days, mentors, setbacks, and pivotal moments that shaped how they lead today. Ray is a longtime ad/media sales leader with experience spanning digital ad tech, CTV, and sports media, and he created The Seat to sharpen his own leadership edge while paying it forward to the next generation of aspiring sales leaders.Social Links:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast (LinkedIn Page)Host: Ray Erickson (LinkedIn)Listen:Apple Podcasts / Spotify / iHeart / SiriusXM / Acast
7. Sean McCaffrey, President & CEO - GSTV
51:05||Season 2, Ep. 7Episode Summary:Sean McCaffrey, President & CEO of GSTV, joins Ray Erickson on The Seat to unpack a 25+ year career spent building at the intersection of media, marketing, and out-of-home. Starting as a young seller in the late 90s, Sean rode the wave of consolidation that shaped modern OOH, grew through 16+ years at Clear Channel, and eventually stepped into the CEO seat at GSTV to build a national video platform at fuel and convenience retail.The conversation spans Sean’s athlete mindset from his Drake football days, how early mentors shaped his leadership style, and why “focusing on what you can control and influence” became a defining principle during a high-stakes period of corporate uncertainty. Sean also shares what surprised him most as a CEO, how board service keeps him sharp, and what he looks for in future leaders; grit, curiosity, and being a perpetual student, especially as AI reshapes every function.Themes Discussed:From athlete to executive: How team sports shape leadership and cultureAccidental entry into advertising & sales and discovering OOH as a careerThe evolution of out-of-home: From static boards to audience-led digital engagementScaling through consolidation: Navigating growth from regional to global organizationsSolutions-based selling: Marketing conversations vs. “selling inventory”Leading through uncertainty: The Clear Channel go-private saga and lessons learnedControl vs. Influence mindset: Why it matters even more in the AI eraMentorship & leadership modeling: Active listening, passion, and high characterCEO realities: Decision-making, consensus-building, and moving fast without perfect infoDeveloping future leaders: Curiosity outside scope, skill gaps, and continuous learningChapters:00:00 - Intro & Sean's Background06:52 - First sales role, Universal Outdoor & “accidental” entry into OOH08:03 - What OOH looked like in the late 90s, regulation, real estate, national vs local11:16 - Consolidation era, Universal/Eller to Clear Channel & learning the full business22:01 - Leading through uncertainty - go-private chaos and the “Venn diagram” framework26:57 - Mentors & values, passion, character, playing the long game32:17 - Why GSTV & CEO lessons, decision velocity, boards, developing leadersKeywords:GSTV, Sean McCaffrey, out-of-home advertising, OOH, DOOH, retail media, convenience retail, video network, Clear Channel Outdoor, leadership, CEO, sales leadership, strategy, partnerships, change management, mentors, decision making, organizational growth, private equity, consolidation, brand safe media, measurement, audience addressability, AI in advertising, executive presence, boards, IAB, Ad Council, OAAA, DPAA, The Seat podcastSean's Bio: Sean McCaffrey is President & CEO of GSTV, the nation’s leading video network at fuel and convenience retailers, reaching over 116 million Americans each month. He previously spent 16+ years at Clear Channel Outdoor, including as EVP of Strategy & Partnerships, leading enterprise revenue strategy and global agency relationships. Sean serves on the boards of the IAB Digital Video Center of Excellence, the Ad Council, OAAA, and DPAA. A former college football player at Drake University, he brings an athlete’s mindset to leadership, culture, and long-term growth.GSTV's Website: https://www.gstv.com/Ray's Bio: Ray Erickson is the host of The Seat, a podcast featuring 1:1 conversations with revenue leaders across media, marketing, and advertising, unpacking the early days, mentors, setbacks, and pivotal moments that shaped how they lead today. Ray is a longtime ad/media sales leader with experience spanning digital ad tech, CTV, and sports media, and he created The Seat to sharpen his own leadership edge while paying it forward to the next generation of aspiring sales leaders.Social Links:Instagram: @theseat.podTikTok: @theseat.podLinkedIn: The Seat Podcast (LinkedIn Page)Host: Ray Erickson (LinkedIn)Listen:Apple Podcasts / Spotify / iHeart / SiriusXM / Acast