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:
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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