🎙️ Guest: Karyn Scott, Fractional CMO & Founding Advisor at Fiat Advisors

🕒 Episode Length: ~30-32 minutes

Episode Overview

In this episode, we sit down with Karyn Scott, a seasoned Fractional CMO who has worked with some of Silicon Valley’s biggest names, including Salesforce, CloudSpot, and Cisco. Karyn shares how fractional leadership is reshaping executive roles, what it means for companies looking to scale efficiently, and how AI is impacting marketing, leadership, and knowledge work.

She also dives into how senior leaders can monetize their expertise in the evolving job market—and what AI’s rapid acceleration means for professionals trying to future-proof their careers.

If you’re a senior leader navigating AI disruption, a marketing exec thinking about going fractional, or just someone trying to understand where AI is headed next, this episode is packed with insights you won’t want to miss.

What You’ll Learn in This Episode:

✅ What fractional leadership actually means—and how it differs from traditional executive roles

✅ Why some companies shouldn’t hire a full-time CMO (and when fractional makes sense)

✅ How AI is changing marketing, storytelling, and leadership—and what leaders should do now

✅ The biggest misconceptions about AI-generated content and how it affects branding

✅ Practical tips on how to monetize your expertise as a fractional leader

✅ Why networking is changing—and how to leverage your industry connections for new opportunities

✅ Karyn’s top lessons learned as a fractional executive (including contract & pricing advice)

Key Quotes from Karyn Scott:

💬 “AI is changing storytelling, but humans still connect with emotion. The best marketers will know how to blend both.”

💬 “A great fractional executive doesn’t just consult—they embed, execute, and create lasting impact.”

💬 “If AI can take over your job, you should be thinking about how to work with it, not against it.”

Resources & Mentions:

📌 Fiat Advisors – Karyn’s advisory firm

📌 LinkedIn – Karyn Scott – Connect with Karyn

📌 HyperWrite – AI for writing & content creation

📌 Runway ML – AI for creative teams

Where to Find Karyn:

📍 LinkedIn: Karyn Scott

📍 X (Twitter): @KarynScott

📍 Instagram: @KarynScott

Enjoying the Podcast?

If you loved this episode, make sure to:

⭐ Subscribe & Review – It helps us bring in more incredible guests!

🎧 Share this episode with someone who needs to hear it!

📩 Send us a voice note at stuck@213studios.com

🚀 Stay tuned for more episodes on how AI is disrupting jobs and reshaping leadership!

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

Building the Future of Work with Jacob Bank

Episode Overview

In this episode, we explore how AI is transforming work with Jacob Bank, CEO of Relay.app and former Gmail product leader. Jacob shares insights from his journey from startup founder to Google executive and back to entrepreneurship, offering practical advice on leveraging AI effectively in business.

Key Topics

• The importance of keeping humans in the loop with AI automation
• How company structures are evolving in the AI era
• Transitioning between startup and corporate environments
• Building successful businesses in an AI-first world
• Practical applications of AI for personal and business productivity

Key Takeaways

• AI works best when humans remain engaged in reviewing and guiding outputs
• Future companies may be smaller but more senior, with AI augmenting capabilities
• The path to entrepreneurship is changing with lower barriers to entry
• Success in the AI era requires authenticity and community building
• Starting with personal productivity use cases is an effective way to adopt AI

Practical Insights

• AI automation examples:
  • Email and calendar management
  • Customer research and communication
  • Content creation and analysis
  • Automated reporting and documentation
  • Video and audio content production

Career Lessons

• The importance of staying close to actual work vs pure management
• How to maintain authenticity while leveraging AI tools
• Why company building is becoming less capital intensive
• The value of finding the right problem vs rushing to market
• Building trust and community in an AI-enabled world

Future of Work Predictions

• Companies will likely become smaller but more impactful
• Junior execution roles may decrease as AI handles basic tasks
• More emphasis on "player-coach" roles combining strategy and execution
• Multiple successful companies can coexist in the same space
• Growing importance of community and authentic connection

Guest Bio

Jacob Bank is the CEO of Relay.app, building AI agent infrastructure to help businesses automate workflows. Previously, he founded Timeful (acquired by Google) and led Gmail as Director of Product Management. His work has impacted over a billion users through AI-powered features in Gmail and Google Calendar.

Resources Mentioned

• Relay.app - AI automation platform
• LinkedIn - Follow Jacob for practical AI implementation tips
• Weekly "Build with Me" sessions - Live AI automation tutorials
• Recommended AI tools:
  • Caption
  • HeyGen
  • Claude
  • ChatGPT

Contact Information

• LinkedIn: Jacob Bank
• Email: jacob@relay.app
• YouTube: Relay.app channel

About Stuck

Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts. Email us: stuck@213studios.com Produced by: Rob Curtis, Jamal Stockton, and Ximena de la Tijera

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

Episode Overview

Meet Jan DAlessandro, who pioneered remote work at AOL in the 90s and now directs billions in corporate philanthropy at Pledge One Percent. Her story shows how lawyers can leverage their skills far beyond traditional practice into business development and social impact.

Key Topics

• How Jan invented working from home at AOL in the 1990s
• Transitioning from corporate law to business development
• Building win-win partnerships across tech, media and entertainment
• Creating sustainable corporate giving programs
• Navigating career transitions in times of uncertainty

Key Quotes

"I got to a point where I thought, I don't really care about the indemnity clause. And then I realized - you can't do this job anymore because somebody needs to care about that. And it wasn't me."

"Culture eats strategy for breakfast every day."

"As a lawyer, you're trained to think critically... to not take things at face value and see how you can turn it into something positive for both sides."

Practical Insights

• Use your legal training as a foundation for other roles:
  • Critical thinking
  • Negotiation skills
  • Deal structuring
  • Understanding multiple stakeholders
• Look for opportunities to merge your professional skills with personal interests
• Consider how your expertise could apply to emerging fields like AI
• Focus on building win-win partnerships rather than just transactions
• Stay connected to what energizes you, even if it means changing roles

Key Lessons for Career Transitions

1. Be honest with yourself about what naturally energizes you
2. Look at what you spend your free time doing - there are jobs related to any interest
3. Focus on transferable skills rather than just industry experience
4. Don't underestimate the value of your professional training in new contexts
5. Consider how emerging technologies like AI create new opportunities in familiar industries

Guest Bio

Jan DAlessandro pioneered work-from-home practices at AOL in the 1990s before transitioning into business development roles at major tech companies. As head of Pledge One Percent's Equity Initiative, she's helped direct over $2.5 billion in corporate philanthropy. Her career spans law, tech, entertainment and social impact.

Resource Mentioned

• Marianne Williamson quote: "Playing small doesn't serve the world"
• Cheryl Sandberg's gratitude journaling practice
• The Innovator's Dilemma by Clayton Christensen

About Stuck

Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts. Email us at stuck@213studios.com. Produced by Rob Curtis, Jamal Stockton, and Ximena de la Tijera.

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera