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

Hosted on Acast. See acast.com/privacy for more information.

Episode 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 & Welcome

02:30 – Telecom Roots & Cold Calling Foundation

08:50 – Startup Life: Growth, Failure & Early Lessons

15:45 – Flurry: Pivot, Survival & Breakthrough

20:10 – Scaling Teams: Hiring & Leadership Development

25:30 – Leading Through Industry Shifts

28:30 – Leadership in Uncertainty & Change

31:30 – Frameworks for Driving Performance

35:30 – Kochava, Growth & AI Opportunity

42:05 – Leadership Philosophy & Path to CR

Themes:

• Leadership development over time
• Resilience and navigating setbacks
• Mentorship and career ownership
• Hiring and team building philosophy
• Adapting through industry/platform shifts
• Growth mindset and continuous learning
• AI and the future of go-to-market
• Customer-centric leadership
• Structure, process, and execution
• Collaboration and cross-functional leadership

Keywords:

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 advertising

Sean'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.pod

TikTok: @theseat.pod

LinkedIn: The Seat Podcast (LinkedIn Page)

Host: Ray Erickson (LinkedIn)

Listen:

Apple Podcasts / Spotify / iHeart / Pandora / Acast / YouTube

Hosted on Acast. See acast.com/privacy for more information.

Episode 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 advertising
• Building global programmatic at The New York Times
• Scaling revenue at Dotdash Meredith
• Lessons from Morning Brew
• Leadership evolution from IC to executive
• The 150% Rule for career growth
• Confidence vs. ego in leadership
• Cross-functional collaboration as a differentiator
• Premium publishing in a changing media landscape
• Mentorship and building a loyal bench

Chapters:

1. 00:00 – Intro
2. 01:43 – Growing Up in St. Louis & Moving to Asia
3. 04:24 – Discovering Ad Tech in Shanghai
4. 07:45 – Early Programmatic at Forbes
5. 10:33 – Leadership Begins at Hearst & The New York Times
6. 15:55 – Scaling at Dotdash & The 150% Rule
7. 19:25 – Imposter Syndrome & Corporate Politics
8. 23:56 – Why The Guardian
9. 32:29 – Red Flags, Hiring & Cross-Functional Growth
10. 40:00 – Morning Brew Lessons & Lightning Round

Keywords

Sara 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 collaboration

Sara'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.pod

TikTok: @theseat.pod

LinkedIn: The Seat Podcast (LinkedIn Page)

Host: Ray Erickson (LinkedIn)

Listen:

Apple Podcasts / Spotify / iHeart / SiriusXM / Acast

Hosted on Acast. See acast.com/privacy for more information.