The Seat
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 [https://www.instagram.com/theseat.pod/] TikTok: @theseat.pod [https://www.tiktok.com/@theseat.pod?is_from_webapp=1&sender_device=pc] LinkedIn: The Seat Podcast [https://www.linkedin.com/company/the-seat-podcast/] (LinkedIn Page) Host: Ray Erickson [https://open.acast.com/networks/68d410fb563e57ba4a72eccc/shows/68d42194d4ea86dd592b51c8/episodes/www.linkedin.com/in/raymonderickson] (LinkedIn) Website: www.theseatpodcast.com Listen: Apple Podcasts / Spotify / iHeart / Pandora / Acast / YouTube ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.
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