Chief Change Officer

#344 Sienna Jackson: From Hollywood to Hard Metrics — Part One


Listen Later

From film sets to SaaS, Sienna Jackson has lived through more than one reinvention. A two-time founder, former entertainment executive, and current tech CEO, she joins Chief Change Officer to break down what it means to build, to create, and to change—on your own terms. 

In Part 1, she shares what it was really like working in the music and production trenches at the Weinstein Company, how she navigated a high-glamour industry with clear-eyed curiosity, and why she never let a job title define her. 

But it’s her unfiltered take on generative AI that steals the show. Sienna dismantles the hype, calling it what it is: regurgitated content dressed as intelligence. From energy waste to algorithmic bias, she unpacks the hidden cost of convenience—and why human storytelling still matters.

Key Highlights of Our Interview:

From Red Carpets to Real Work

“All the Quinton Tarantino films, all the Oscar Batty films… Project Runway… I also worked on our internal music catalog… and it would just be usually me and Richard for most of that run.”

Curiosity > Career Ladder

“I thought I was going to be the rebel… I was doing things during the Arab Spring… I also reported on the honor killing of one of my classmates when I was 16.”

AI ≠ Creativity

“Some people will say AI-generated art is art. And I think that’s a misnomer… Art is an action. It’s something that you do. It reflects technical skill that you have to develop over time.”

The Hidden Cost of ‘Smart’

“There are human beings at the other end of the pipeline… being paid pennies on the hour to train chatbots… it uses up 10 to 30 times more energy.”

Garbage In, Garbage Out

“GenAI will reify or reinforce patterns… there’ve been significant issues with algorithmic bias on the axes of race… who gets an insurance policy or not.”

___________________________

Connect with us:
Host: Vince Chan | Guest: Sienna Jackson

 

--Chief Change Officer--
Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence
for Transformation Gurus, Black Sheep,
Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.
20 Million+ All-Time Downloads.
80+ Countries Reached Daily.
Global Top 1% Podcast.
Top 5 US Business.
Top 1 US Careers.

>>>180,000+ are outgrowing. Act Today.<<<

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

...more
View all episodesView all episodes
Download on the App Store

Chief Change OfficerBy Vince Chan

  • 4.5
  • 4.5
  • 4.5
  • 4.5
  • 4.5

4.5

41 ratings


More shows like Chief Change Officer

View all
The Ramsey Show by Ramsey Network

The Ramsey Show

38,780 Listeners

HBR IdeaCast by Harvard Business Review

HBR IdeaCast

177 Listeners

The $100 MBA Show by Omar Zenhom

The $100 MBA Show

1,107 Listeners

Find Your Dream Job: Insider Tips for Finding Work, Advancing your Career, and Loving Your Job by Mac Prichard

Find Your Dream Job: Insider Tips for Finding Work, Advancing your Career, and Loving Your Job

619 Listeners

How to Be Awesome at Your Job by How to be Awesome at Your Job

How to Be Awesome at Your Job

1,027 Listeners

Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing) by Hala Taha | Entrepreneurship, Sales, Marketing | YAP Media Network

Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)

1,293 Listeners

The Prof G Pod with Scott Galloway by Vox Media Podcast Network

The Prof G Pod with Scott Galloway

5,414 Listeners

A Bit of Optimism by Simon Sinek

A Bit of Optimism

2,190 Listeners

3 Takeaways by Lynn Thoman

3 Takeaways

256 Listeners

Huberman Lab by Scicomm Media

Huberman Lab

28,507 Listeners

Passion Struck with John R. Miles by John R. Miles

Passion Struck with John R. Miles

705 Listeners

Money Rehab with Nicole Lapin by Money News Network

Money Rehab with Nicole Lapin

1,636 Listeners

The Mel Robbins Podcast by Mel Robbins

The Mel Robbins Podcast

20,604 Listeners

HBR On Strategy by Harvard Business Review

HBR On Strategy

84 Listeners

The Jefferson Fisher Podcast by Civility Media

The Jefferson Fisher Podcast

8,054 Listeners