Chief Change Officer - #344 Sienna Jackson: From Hollywood to Hard Metrics — Part One

Episode Date: May 4, 2025

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.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist community 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 Spineglass 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 L.A. 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 here. 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 hindsight, 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 Angelino. 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. You are in the SaaS B2B space. What kind of software are you building? Who is the fool and what problem is it solving? Yes, the company that I'm building is called Norcara. It's a HR compliance automation tool.

We'll just quite a pivot away from working in the entertainment industry, but actually not quite so much when you look at my history. And we're focused on identifying and managing risks, telling an employer, hey, based on your current practices and the data that we're seeing, here's your likelihood that you'll be sued by your employees for things like discrimination, wrong determination, harassment, and all the rest. You've spent over a decade in the TV and film industry, including time at the iconic Weinstein Company, which, as we know, produced many major movies.

Just a few weeks ago, I rewatched Kill Bill, one of my all-time favorites. But of course, there are many others. How did you first get into TV and film? Was it a childhood dream? A deep passion for entertainment? Or did something else pull you into that world? It was a lucky break, to be honest, because when I was a teenager, like I'd started college when I was 14 years old, and I was majoring in journalism and

political science. So my real passion was to work in either journalism 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 in within the Armenian community in Los Angeles. So I was really interested in like the degree of 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. 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 40s. 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 would then start 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 Linings 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. By the way, I also really enjoy the tang speech. Calling Firth was fantastic and the whole production was beautifully done. So you started off as an intern and eventually joined full-time. Your role was more behind the scenes. Exactly what you were doing there. Yeah, so working in a music department at a studio, typically those departments are pretty substantially lard at Weinstein for so many reasons just about the way that company

was managed. Our music department was never more than three people, so that meant I was doing day-to-day, both creative and admin on all of our film 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 had the rights to. Copyright-wise, I was in charge of managing and pulling together those rights because we had a global license. 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 over 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 helping things as we went along.

Listen, I 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, 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. But to your point about maybe not being fully contented with that, I spent a lot of my time when I wasn't

at the office or going to an album listening party or screening or any sort of thing after dark or after hours, I spent a lot of time volunteering and doing things like extracurriculars that were non-promotable labor within the company. 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 21 in the U.S. 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 gonna 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, it's that instinct to expand beyond what's expected.

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-dollar 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. And it's something that you do to live. And like all industries fundamentally, they're jobs, right? They're just, they're 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 LA is very much like the DC of the West coast. What do you think about like our consular corps and all of the different geopolitics that are actually LA makes itself very relevant to. 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, the people that I've run into or the contacts that I have in my phone, vis-a-vis 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. AI. Over the past two years or so, it's become a huge disruptor. We've seen strides, 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 prompts.

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? Yeah, 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 thriving 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 as consumers, as people who are exposed to media for a long time. When you think about the curation of your social media feed, the algorithm that drives what you see every day. When it comes to like generative AI or like 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 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, part of the reason why WGA and Saidafra 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 it 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 in it reflects a craft, it reflects technical skill that you have to develop over time. And when 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,

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 be 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 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 artist 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. It gives you all of this rich context and subtext that AI just doesn't have because what it's doing is taking a bunch of existing IP, topping it up like a chopped salad, fitting it out. And there's a reason why you mentioned like OpenAI partnering with news and media. There's a reason why they're being sued by multiple of those parties because their work has been taken advantage of

without compensation and without consent. And that's the problem with a lot of these like LLMs and these large data sets are used to train these models. They're just vacuuming things off the internet willy nilly and not being forthright about where they're sourcing the data, which is why we've had certain, a couple of scandals where child abuse materials were used to train AI models and showed up in outputs.

You've got, I think Elon Musk with Rock, he's turned off all the safety controls or the content controls on what images can be used and what IP is being exploited. So I think the thing about AI is it's such a convenient tool. It's a convenience. It's really more than anything else. It's not truly intelligent. It's not a problem solver. It doesn't come up with anything new. It just fits out what's given. not a problem solver. It doesn't come up with anything new. It just spits out what's given. That's the reason why people actually use tools like ChatGPT. It's finished out this presentation for me because I don't want to take the time to actually, I'm too tired,

I'm too busy, I don't have the time to actually sit down and think about it. So just do it for me. In the same sense that when it comes to art and creativity, when people use JNI, it's because it's an easy excuse not to have to do art. Like, why am I gonna sit down and read a book that no one could be bothered to write? Why would I sit and watch a movie that no one worked on? We talk a lot about convenience, smartphones, smart apps, smart everything.

But I wonder how high is the cost we have paid for that convenience? Long before generative AI, we were already handing over bits and pieces of our thinking to machines. WhatsApp makes global texting easy. In exchange, we've lost other things, like attention span, quality time, memory capacity, even basic writing skills. I grew up in the analog world. I transitioned into digital, but I still carry that early training with me.

I still check my spelling, not spell check in the software, but in my own brain. Before I hit a button, I still do mental math. I want to keep certain muscles sharp because once they are gone, they are hard to get back. And when it comes to AI, especially in creative industries, I worry the cost of convenience is growing. And we haven't really calculated the laws clearly.

There is pretty substantial research. So that actually has assisted in the work I do now in social impact, because a lot of what I'm focused on now with Zorin Creative Strategy, my social impact consulting firm, is on how we quantify either good or harm, right? I deal with situations where companies will say, oh, we're making so much of a great impact in this and that way, or this, that, and the third. And I'm like the auditor who comes in and says, okay, all right, by what degree, by

what measure are you making that impact? And who are your stakeholders? Who are you impacting? And why and how? When it comes to generative AI currently, it uses up 10 times more electricity. It's 10 to 30 times more energy. The demand for data centers has major environmental impacts.

The mental health damage. There was a headline I saw recently about tenions who are being paid like pennies on the hour to train chat bots and algorithms. And they're just being firehosed with the most awful disturbing content. And they're having to like, so they're a real human. So it's not just a smart machine. There are human beings at the other end of the pipeline. A lot of them are actually really suffering to develop, to deliver this convenience to us, wealthy consumers.

And I'm saying that as someone who, yeah, Gen.AI is very convenient. It's very useful. Like, I've used those tools. I've played with those tools. I think it's important for people to know and understand how those tools work. I think it's important for us to not be afraid of learning about new technologies that are available because if we don't know them and understand them, other people will and those are the people that are capitalizing on it. And if you think about algorithmic

bias now, think about the impact of using AI tools to evaluate health insurance claims. Think about the potential fallouts of using AI to evaluate a housing insurance claim. Because there are there. I'm also a member of the National African American Insurance Association. So I have some feelers in the insurance industry, there's been some significant issues with bias, algorithmic bias on the axis of race when it comes to how these tools are applied to who gets an insurance policy or not, or how much coverage they receive or not. And you start to see patterns. So what a lot of Gen.A. does, it's garbage in, garbage out. It will just, it will

reify or reinforce patterns. So if you're getting at biases, implicit or not, it's just going to reinforce those biases. The risks are pretty great when it comes to both the human costs and also the environmental costs, which is ultimately something that we foot the bill for as human beings. And then I think another thing to consider is just the spread of disinformation and deepfakes. Now that Sora is available to the general public to paid subscribers, you're going to see a lot more flooding of our social media with altered images, right? Altered video that will look so convincing and so persuasive. And if people don't develop the skill sets to recognize what is real and what is fake and how to differentiate,

but the problem is like human brains are not good at differentiating between real and fake evidence. We tend to take things in as given and doing the critical thinking later of wait, did that make sense? What I just saw people don't really do that unless you really train them to do it. It's not our first instinct to be like, your first instinct is doom scrolling. Your brain is just vacuuming up what it sees and not saying, hey, wait a second, that was, how many fingers were on that hand? You know what I mean?

That's where we'll stop for now. Sienna took us from newsroom to red carpet, Hollywood power games, generative AIs, creative limits, and the deeper purpose she's been chasing all along. In part 2, we shift gears from content to cause. She will take us inside the impact space, how to measure real change, why siloed thinking is a barrier, and how she's building alliances that connect culture, capital, and community across continents. Real talk, sharp thinking, and a deeply human-centered mission. Don't miss it! Thank you so much for joining us today. If you like what you heard, don't forget, subscribe to our show, leave us top rated reviews, check out our website, and follow me on social media.

I'm Vince Chen, your ambitious human host. Until next time, take care.