Apple, Adobe and Beyond: How Matt Strain Became an ‘AI Whisperer’ - Episode 44

Pivot points powered by Brandpie

Pivot points powered by Brandpie
Apple, Adobe and Beyond: How Matt Strain Became an ‘AI Whisperer’ - Episode 44
Jul 22, 2026 Episode 44
Brandpie

Forbes has labelled Matt Strain as the ‘AI Whisperer’. 

But what connects him to the world is not the technology he uses, but the people he keeps closest.

Matt is a man of great ambition, always willing to leave comfort in search of something new - his departure from prestigious roles at Apple and Adobe should be proof-enough of that…

For leaders trying to find the balance between the safe play and the ambitious one… between embracing technology and prioritising humanity… Matt Strain gives us the roadmap.

You will learn:

  • How Matt Strain navigated pivotal career moves from Apple and Adobe to becoming an “AI whisperer”
  • Why culture and relationships often matter more than strategy
  • What an ‘AI Readiness Audit’ looks like in practice, and the hidden gaps it tends to reveal
  • How CEOs and executives can start using AI in their own lives and work to model healthy, responsible adoption
  • Practical ways to use AI to become a more thoughtful, creative and effective human

🔑 Key Themes

  • Career pivots and purposeful risk-taking
  • Culture, integration and the power of people
  • AI readiness, leadership and organisational culture
  • Being more human in an AI-driven world

Matt Strain

https://www.linkedin.com/in/mattstrain/

The Prompt

https://www.the-prompt.ai/

https://www.linkedin.com/company/thepromptai/

Connect with Dave Allen: https://www.linkedin.com/in/daveallenbrandpie/
Learn more about Brandpie: https://www.brandpie.com/
https://www.linkedin.com/company/brandpie/

Episode Artwork Apple, Adobe and Beyond: How Matt Strain Became an ‘AI Whisperer’ - Episode 44 48:33 Episode Artwork The Selfless Path to Getting What You Want with Co-Founder of Acertitude, Kevin O'Neill - Episode 43 45:03 Episode Artwork Path to the Big Leagues: How Relationships Built a Dream with Founder & Managing Partner of 1440 Sports, Ricky Paugh - Episode 42 39:43 Episode Artwork The Olympian’s Mindset: Creating a Winning Team with Gold Medal Winner & President of Swimathon Foundation, Duncan Goodhew MBE - Episode 41 35:13 Episode Artwork Creating the Long-Term Antidote to Short-Term Politics with Co-Founder of The National Strategy Project, Catherine Day - Episode 40 36:50 Episode Artwork Nordic Series: Culture and Trust on a Global Stage with CEO of Scatec, Terje Pilskog - Episode 39 44:15 Episode Artwork Nordic Series: The Gold Standard of Healthcare with Thor Medical’s CEO, Jasper Kurth - Episode 38 36:35 Episode Artwork Nordic Series: Leading Through Geopolitical Chaos with Steinar Sønsteby, CEO at ATEA - Episode 37 39:22 Episode Artwork Leading When Failure is Not an Option with CEO of Dynavox Group, Fredrik Ruben - Episode 36 41:04 Episode Artwork Making Your Own Luck: Huma’s Journey to its Billion Dollar Valuation with Founder & CEO, Dan Vahdat - Episode 35 34:28 Episode Artwork The Brains Behind Baker Tilly’s Breakout with CEO at Nichols Cauley, Alan Whitman - Episode 34 38:57 Episode Artwork Accidental Career, Purposeful Leader: Lucy Knill’s Journey to Anthropy CEO - Episode 33 42:36 Episode Artwork Building for Years, Not Quarters: How to Balance Slow Opportunities with Time Pressures with CEO of HS Orka, Tómas Sigurðsson - Episode 32 38:39 Episode Artwork Ripping Up the Playbook to Innovate in Novel Industries with OxWash Founder & Exited CEO, and Ex-NASA & SpaceX, Dr Kyle Grant-Talbot - Episode 31 37:22 Episode Artwork 2026: The Trends of a Successful Leader - Episode 30 49:01 Episode Artwork Transparency at the Top: How Authenticity Creates Culture That Lasts with CEO of Securian Canada, Nigel Branker - Episode 29 37:23 Episode Artwork Flipping the Script: How to Overturn the Recession in Moral Leadership with Co-Founder of Apolitical, Robyn Scott - Episode 28 41:00 Episode Artwork The Intentional Brilliance of an Accidental CEO with Senior Advisor and Former-CEO of Flatiron Health, Carolyn Starrett - Episode 27 40:20 Episode Artwork Charting the Map for Transformative Leadership with Ordnance Survey’s CEO, Nick Bolton - Episode 26 46:37 Episode Artwork ‘Change Happens at the Speed of Trust’: Reshaping Healthcare with Confluent Health CEO, Kristi Henderson - Episode 25 35:16 Episode Artwork ‘Sink or Swim’: Mastering the Transition from Life-Saver to Leadership with CEO at CORCYM, Christian Mazzi - Episode 24 42:52 Episode Artwork The Founder’s Edge: Secrets to Growing Alongside Your Business with Entrepreneur and Investor, Dave Parker - Episode 23 41:26 Episode Artwork The Art of Reinvention Across Companies and Continents with CEO of British American Business, Duncan Edwards OBE - Episode 22 37:09 Episode Artwork Saving the World: How Purpose Guides Progress with CEO of Nexpring Health, Wil Boren - Episode 21 40:18 Episode Artwork Turning Points: A Pivot Points Special - Episode 20 26:07