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 Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Sienna Jackson and what is her background?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist humility for change progressives in organizational and human transformation from around the world. Today's guest is Sienna Jackson, a two-time founder, systems thinker, and someone who's been rewriting the rules since she was a teenager.
We were introduced through a former guest, Chris Hare. And right away, I knew we spoke the same language. Real talk, human-centric ideas, and sharp thinking with no fluff. Sienna started college at 14, interned at the Weinstein Company by 17, and later led music and content at Spine Glass Media.
Today, she is the CEO and co-founder of Notera, a B2B software company helping large enterprises control the risk of employment litigation and automate HR compliance. And yes, AI plays a big role in that. In this two-part series, We talk about chasing excellence without burning out, navigating boardrooms as the only one in the room, and why equity has to be measured if you want it to matter.
Let's get into it. Sienna, good afternoon to you in LA. Thank you so much for joining me on Chief Change Officer.
Thank you so much for having me, Vince. This is so much fun.
You were introduced to me by our common friend, Chris Hare. In fact, Chris has so far connected me with more than five amazing people for this show. All of them have come on board the power of real human networking. Sienna, let's set the stage for today's conversation. You are in the US, you are based in LA, but tell us, what are you doing now? And just as importantly, what were you doing before?
Walk us through how that transition happened, and then we'll dive into the details, your insights, your high side, and everything in between.
Gotcha, so me in a nutshell. Okay, let me try. My name is Sienna Jackson. I'm a two-time founder. I'm born and raised Angeleno. I used to work in the entertainment industry for many years on a lot of film and TV projects you may have seen. And like I said, I'm a two-time founder. I've built a social impact consultancy.
that works on driving change at the intersection of cause, culture and capital. I'm also a tech founder and I'm building a B2B SaaS company. So I wear a lot of different hats and I think that's probably going to be the bulk of our conversation is why I wear all those hats and how I fit them on this hair.
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Chapter 2: What was Sienna's experience like at the Weinstein Company?
or maybe working in the public sector, like specifically like State Department or in intelligence, because when I started college at that time, it was right before Obama won his first term in office. So that was like a really different, optimistic, exciting time. It was amazing to be engaged. in the news and current events.
And I was personally very interested in international relations and international and current affairs. So I was doing things like during the Arab Spring, I was reporting on that. I was talking to students that were protesting in Tahrir Square in Tunisia and asking them questions like, hey, I'm a student reporter. from the United States and I'd like to talk to you about why you're protesting.
So I was really interested in what was going on in the region. I was like one of the senior staff reporters for my college paper when Osama bin Laden was killed. And I remember filing the story about that for my college paper.
The night that was announced, like, I was at a cafe or something that also reported on really serious issues like the honor killing of one of my classmates when I was 16 that was within the Armenian community in Los Angeles. So I was really interested in, like, serious stuff. But my whole family works in the entertainment industry and I thought I was going to be the one to not do that.
Like I was going to be the rebel that would do something that would be a reporter. But I got the opportunity to have an internship at the Weinstein Company when I was just turned 17. And I walked into that interview and I walked out with the job and my boss at the time, Richard Glasser, who is of like... classically old school. He was born in the forties.
He's worked with like Quincy Jones and Stevie Wonder, and he's been just absolutely all over the place when it comes to the music industry. He really saw a lot of potential in me and mentored me and gave me the opportunity to work part-time as I was getting my following degrees. in journalism and communications. This was around 2008. No, it was 2010 when I started interning there.
And at the time we were post recession, job security was scarce. So I was handed this amazing opportunity. I was like, this is not my plan, but I should take it and run with it because Who would turn away an opportunity like that? And because of that, I got to work on a lot of amazing projects, like a lot of Quentin Tarantino's work up through Hateful Eight.
When I started there as an intern, they were in post-production on The King's Speech, which put them off that run, that kind of legendary two, three year sprint of getting best picture over and over. So it was like The King's Speech, The Artist, Silver Mining Playbook. getting a lot of Oscar noms in those early years, those Obama era years.
And then I did a lot of other things on the side during that period. So it was just like, it was happenstance that I got that opportunity, but I took it and I ran with it.
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Chapter 3: How did Sienna transition from entertainment to tech?
Yeah, so working in a music department at a studio, typically those departments are pretty substantially large. At Weinstein, for so many reasons, just about the way that company was managed, our music department was never more than three people maximum. So that meant I was doing day to day. both creative and admin on all of our filming and TV projects.
So that was all the Quentin Tarantino films, all the Oscar Beatty films that we did, all the TV shows like Project Runway, it was like Scream and Scary Movies, like the Dimension label films, stuff that was like Radius TWC. It ended up being like clearing music for our trailers. doing sometimes in-house music supervision. So that's like how music that you see in a film.
So say you're watching a scene in a movie and a popular song comes on. Someone had to choose that song for that scene and someone had to go and negotiate the rights to use that music. Sometimes I'd be doing that. We also did a lot of original songs with folks like Taylor Swift and U2 and Eminem, Lana Del Rey, Gwen Stefani, Pharrell Williams.
So being part of the process of negotiating those deals and dealing with our rights, I also worked on our internal music catalogs, everything that we have the rights to. Copyright wise, I was in charge of managing and pulling together those rights because we had a global community. We had a global publishing deal with BMG, which is a very large music rights company.
So it was a lot of things that typically would be split amongst multiple teams, but it was just usually me and Richard for most of that run.
And like you said, it was a lean, high efficiency team doing a huge volume of work. So you had the chance to touch almost every area. How did you feel about the experience? I know you once thought of yourself as a bit of a rebel, not planning to enter this industry at all. But then you got the job offer and eventually became a driving force behind the scenes.
Was it just go, go, go every day, no time to pause, just riding the momentum? Or even when things looked great from the outside, great income, exciting projects, fantastic encounters with these stars, did part of you already start sensing, this isn't the full story of who I am? Were you quietly searching for something more?
Yeah, so it's interesting. Looking back now, because it was such a Wild West sort of environment, I feel like that job prepared me for entrepreneurship in retrospect because having to manage every little piece of something is the life of an entrepreneur. So I was already doing it without realizing. And sometimes it really did feel like we were bootstrapping or building things as we went along.
Listen, it was like my teens and early 20s when I really got my feet under me in that career. I was going out to like shows every night. Like I was on the invite list for different parties. So for me, it was great because I got to enjoy that life at the perfect period in my life.
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Chapter 4: What challenges does Sienna face in her current role?
Richard and I were on the LA Music Leaders Roundtable, which was, it was like a think tank, essentially. We were lobbying Congress and working very closely with Congresswoman Judy Chu under the House Judiciary Committee to advocate for creators' rights. So I was getting to do some, like, government affairs and lobbying work before I was even legal to drink. Right.
I was before the drinking age, I was just 21 in the US and I was doing grassroots organizing with ACLU in California and doing all these other things on top of my day job, which was focused on using music to bring stories to life or working with artists and creatives to make original songs that were deeply impactful or that tell a story.
And some of the projects that we worked on, that company was really an important mini-major studio in American cinema when you think about the history of American filmmaking and how films are bought. So we were doing a lot of cool, innovative stuff.
But I always found time to pursue my other interests because I'm the sort of person where it's like, I can't just do one thing because I'm not content. And I think by the tail end of that 10 years, I really was feeling like, what am I, what else am I going to do? Because I can't just do this forever.
I can see that you are like me. Even when you have a full-time job, you're not just checking boxes. You are constantly thinking, what else can be done? What's a better way to do this? No one's asking you to take on more, but you do it anyway. Because there's that inner fire, that curiosity. is that instinct to expand beyond what's expected.
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Chapter 5: What is Sienna's perspective on the role of AI in creativity?
From the outside, the entertainment industry looks glamorous, just like when I worked in finance and investment. I interned at Goldman Sachs New York headquarters. I was an investor in LA for a firm called TCW Asset Management, a multi-billion dollars institutional fund manager. On paper, that was someone else's dream job.
Los Angeles, global deals, high stakes, first class air ticket, all the parties, all the prestige. But behind that shine, It was exhausting. And eventually, I had to admit, I wasn't fulfilled. So that's why I asked, even when you were deep in the world of movie making, doing exciting work and moving fast, was there a part of you that thought, this isn't it. This isn't the whole me.
And at what point did that awareness push you towards a different path? something that felt more aligned with who you really are.
Yeah, I think it's not that that wasn't the real me or that wasn't a valuable time of my life. It's just that I think it's important to have healthy boundaries between your personal identity and your identity at work. I think Americans live to work when it's something that you do to live. And like all industries, fundamentally, their jobs, right? They're just their industries.
I see LA as like a company town in the same way that like a coal mining town in Virginia is a company town, right? Or DC is a company town because everyone works in politics and it's just work. And L.A. is very much like the D.C. of the West Coast. When you think about like our consular core and all of the different geopolitics that are actually L.A. makes itself very relevant to.
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Chapter 6: What are the hidden costs of generative AI?
So like all of these different industries and there's a lot of overlap, too. So when I was, again, in that period of time during the Obama years. There was a lot of overlap between DC and Hollywood, like a lot, a lot.
And it's funny that people that I've run into or the contacts that I have in my phone vis-a-vis that that relationship, that special relationship, especially when the person who ran your company was like a major Democratic donor.
You've left the movie industry, but I want to ask you about something big that has shaken it. A.I. Over the past two years or so, it's become a huge disruptor. We've seen strikes, partnerships between AI and media companies, and a growing reliance on machine-generated content. You've worked in the real creative trenches with people, not problems.
So I'm curious, how do you feel about AI entering the world of storytelling? What does it mean for the human side of creativity?
As someone who advocated for creators' rights, I don't think, first of all, AI is not new. Like the generative AI that we're seeing, we've had algorithms driving things for a long time now. And a lot of the underlying technology that we're talking about is actually not all that new. And algorithms have been influencing us and influencing our lives now.
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Chapter 7: How does Sienna view the importance of human storytelling?
As consumers, as people who are exposed to media for a long time, you think about the curation of your social media feed, the algorithm that drives what you see every day. When it comes to generative AI or open AI as an example, I don't think it is a positive change for the industry, for these larger companies to think, oh, here's our excuse to either eliminate people's jobs or to underpay people.
Because at the end of the day, generative AI, it's not generating anything unique. It's taking what's given, right? And regurgitating out. It's not even, I wouldn't even call it a derivative work because there's no work being done by a person. It's not creation. We don't call it creative AI. It's generative AI because you're just generating something from a prompt.
When people say that part of the reason why WGA and SAG-AFTRA and other unions were renegotiating their contracts with the studios and were picketing is this idea that AI is going to be used to abuse workers, which very well can be. And we see that that's what happens. And to create content that isn't really art. So some people say generative AI, AI generated art is art.
And I think that's a misnomer because it's an excuse. Art is an action. It's something that you do something and it reflects a craft. It reflects technical skill that you have to develop over time. And when, you know, you as an artist, you as a creative are making something or expressing something, you're expressing a point of view that is your own. You have to be the author of
That point of view or that thing that you're creating. And it requires technical skills. And if we say that someone who's like a prompt engineer sits down and throws in a couple of prompts to chat to PT and generates a screenplay, that person is not a writer for having inputted a full different prompts and generate...
because they don't know how to write if you were to put a gun to their head and say write like a 20 minute short they couldn't do it right because they don't actually have the skill so i think a lot of the way that gen ai is being used abusively or could be used abusively in the industry is it's an excuse not to develop the real skills to create
And what it robs people of is the ability, first of all, to learn and improve at something through hard work and real talent and just achieving a certain amount of technical prowess. And then it also robs people of the ability to actually engage with each other.
art is not just about creating content right that can be monetized or commercialized art is really about expressing something that is incohate something that is internal to you something of your own interiority that you're making tangible to the world so that other people can see it and understand it and connect with you so that human connection piece is the critical function of art like when we think about
critique of art or we think about, if we look at a painting that was painted in the 17th century, the techniques that are used, the choice of color, like the decisions that the artist makes when they create that piece of work tells us not only something about the artists themselves and their point of view and the life and times that they were living through in their own human experience, but it also gives you a glimpse into the world that they lived in.
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