#345 Sienna Jackson: From Hollywood to Hard Metrics — Part Two

Summary

Chief Change Officer Episode #345: Sienna Jackson – From Hollywood to Hard Metrics (Part Two)
Release Date: May 5, 2025

Introduction

In episode #345 of Chief Change Officer, host Vince Chan engages in a compelling two-part conversation with Sienna Jackson, a two-time founder and systems thinker. This episode delves deep into Sienna's transition from the entertainment industry to the realm of social impact, exploring her journey, methodologies, and the challenges she has encountered along the way. The discussion provides invaluable insights for growth progressives, visionaries, and changemakers aiming to outgrow themselves and effect meaningful change in the world.

Sienna’s Career Transition: From Entertainment to Social Impact

Sienna Jackson's career trajectory is nothing short of inspiring. Starting college at 14 and interning at the Weinstein Company by 17, Sienna quickly made her mark in the entertainment industry, leading music and content at Spine Glass Media. However, her passion for social good and storytelling eventually led her to pivot towards impact consulting.

At [05:10], Sienna explains, “I wanted to be a citizen of the world and use storytelling through the lens of reporting for good.” Disillusioned by the state of journalism and recognizing the shifting landscape of entertainment with the rise of streaming, she decided to chart a new path. By early 2020, Sienna had established her consultancy, Notera, a B2B software company that leverages AI to help large enterprises manage employment litigation risks and automate HR compliance.

Approach to Measuring and Creating Impact

Sienna emphasizes a structured approach to impact, defining it as “the net positive change rendered as a direct and material result of your actions” ([05:10]). She critiques the prevalent use of "impact" as mere marketing jargon, advocating instead for measurable and predictable outcomes. Her focus lies in Impact Management and Measurement (IMM), utilizing tools like Social Return on Investment (SROI) analysis to create tangible, data-driven impact models.

She elaborates, “If you get an input, an action, you should get a specific reaction or outcome that you can measure, that you can quantify, that you can predict” ([05:10]). This rigorous methodology ensures that impact initiatives are not only well-intentioned but also effective and scalable.

Current Projects and Initiatives

Sienna is currently channeling her expertise into some of the most significant projects in her career. Notably, she is executive producing the Great Rift Valley Innovation Summit in Ethiopia, a collaborative effort with the United Nations Development Program (UNDP). This initiative aims to provide non-dilutive funding to Ethiopian entrepreneurs excelling in healthcare, education, and agriculture ([10:45]).

Her role involves bridging diverse stakeholders across public and private sectors to foster innovation and economic development in Africa. Sienna’s ability to “speak to people in their own language and draw them together” is highlighted as her key strength in building effective coalitions ([22:02]).

Challenges in Impact Work

Throughout her journey, Sienna has encountered several barriers, primarily revolving around the lack of a professional peer community and effective networking within the impact sector. At [15:56], she states, “the big thing that I noticed right out the gate was a lack of professional, peer community and network.”

She identifies silos as a significant obstacle, where different sectors (nonprofits, private sector, etc.) fail to communicate effectively. To address this, Sienna is actively working on creating industry surveys and building a more structured community for impact practitioners through her role at Social Value International ([18:15]).

Final Thoughts and Advice

Closing the episode, Sienna offers a powerful message to aspiring changemakers: “Every single person has their own unique way of doing good in the world. You have something unique to offer that's entirely yours” ([23:01]). She encourages individuals to identify their unique skills and collaborate with existing helpers to maximize their impact.

Vince echoes this sentiment, emphasizing the importance of execution, data collection, and strategic decision-making in scaling impact initiatives ([24:21]). Sienna’s concluding remarks reinforce the idea that impactful change stems from clarity, curiosity, and the courage to take the first step.

Conclusion

This episode of Chief Change Officer showcases Sienna Jackson’s remarkable journey from Hollywood to the forefront of social impact. Her blend of creative storytelling and rigorous impact measurement provides a blueprint for others seeking to drive meaningful change. Sienna’s insights into overcoming industry barriers and her dedication to fostering global collaborations underscore the essence of true leadership in the transformation space.

If you’re inspired by Sienna’s story and eager to embark on your own path of outgrowing yourself, tune into Chief Change Officer on LinkedIn, Apple, Spotify, and YouTube @chiefchangeofficer. Join the community of over 130,000 followers dedicated to ambitious human transformation.

Notable Quotes

• “If you get an input, an action, you should get a specific reaction or outcome that you can measure, that you can quantify, that you can predict.” – Sienna Jackson ([05:10])
• “You can't silo yourself.” – Sienna Jackson ([18:15])
• “Every single person has their own unique way of doing good in the world.” – Sienna Jackson ([23:01])

Transcript

[USAA]

USAA knows dynamic duos can save the day like superheroes and sidekicks or auto and home insurance. With USAA you can bundle your auto and home and save up to 10%. Tap the banner to learn more and get a'[e-mail] bundle restrictions apply.

[Amazon Pharmacy]

Amazon Pharmacy presents Painful Thoughts 20 more minutes to kill in the pharmacy before my prescription is ready. Maybe I'll grab some deeply discounted out of season Halloween candy. Hmm. I never had a chocolate pumpkin with raisins before. Those were raisins, right? Next time use Amazon Pharmacy. We deliver. And no, those were not raisins. Amazon Pharmacy Healthcare just got less painful.

[HubSpot]

With HubSpot's suite of AI powered tools you can get more done way faster, speed up your lead generation and create attention grabbing, lead driving, quota crushing campaigns in an instant. Get started [e-mail] AI look around.

[Autotrader]

You can find cars like these on autotrader. New cars, used cars, electric cars, maybe even flying cars. Okay, no flying cars. But as soon as they get invented they'll be on autotrader. Just you wait.

[Amazon Pharmacy]

Autotrader Building a business may feel like a big jump, but on deck small business loans can help keep you afloat. With lines of credit up to $100,000 and term loans up to 250,000 DOL, OnDeck lets you choose the loan that's right for your business. As a top rated online small business lender, OnDeck's team of loan advisors can help you find the right business loan to fit your needs. Visit ondeck.com for more information. Depending on certain loan attributes, your business loan may be issued by Ondeck or Celtic Bank. Ondeck does not lend in North Dakota. All loans and amounts subject to lender approval.

[Vince Chen]

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 teenage. 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. That brings us to a good segue. Your social impact work, what made you step into that space in the first place? You mentioned earlier about being like an auditor, someone who helps organizations understand the impact they've made, both the good and the unintended. But let's rewind a little. What drove you to move from the movie making industry into social impact? And second, how would you describe your own approach to measuring and creating impact?

[Sienna Jackson]

We'll put the. We'll separate that into two buckets. So like when I was in my kind of mid-20s, by the time I was like, yeah, approaching like 27. No, even earlier than that. It would have been a couple years even before that. So as I was like moving on through my career, I was doing all this stuff on the side for free of just like meddling in politics and doing things that were social good oriented. But even before that, I wanted to be a journalist, right? I wanted to be a citizen of the world and use storytelling through the lens of reporting for good. But I saw that journalism as an industry was already, yep, in a very bad way when I pivoted into entertainment. And by the tail end of my time in entertainment, so much had been changing in the industry. And I would say to like, friends, I'd be like, streaming's going to become the new cable. They're going to want to cut the cord. Streaming, they're going to do bundles. Of course, like four years later, that's exactly what was happening. And I was just ready to pivot. I think I have a diary entry from like December 2018 of Sienna. You need to figure out what you want to do with your life and you've got to like, figure it out and just do it. That was 2018. I didn't start the startup, my consultancy, until 2020, but I had created the LLC in 2019. I started like, I bought a domain. I started like just subconsciously doing little things that were like my offering to get ready for the pivot. It wasn't like a plan that I had in mind. And then in January of 2020, right after Grammy week, I sent an email to like, my top, you know, top couple thousand most relevant industry contacts. I was like, I'm doing stuff for impact now. Okay? And that was it. And then March happened and lockdown started. And I was like, oh, great timing to Start a business. That was the year 2020 was such an inflection year, culturally in the United States after the murder of George Floyd, people were calling me up and asking how they should think about things. Because people already had known me and knew what I was about. They knew I was always interested in the world and current events, and I had my fingers in a lot of different pies and I had relationships and networks outside of the entertainment industry. People already knew what I was, that I was eclectic in my areas of interest. So people would hit me up and I said, okay, I'm happy to have the conversation, but you have to pay me for it. And so that's what kicked me off, was like one email. And that kicked off my entire career as an impact consultant. And as I started doing that, like, right out the gate, I worked on like 2020 presidential election. So I worked on a big get out the vote campaign that ultimately registered like 114,000 voters. So I was already, like, right out the gate doing a lot of really cool projects. And it became quickly apparent to me that people were jumping on the impact train, this idea, and making a lot of claims that were. It was just like, it was just like marketing shtick. It was like hollow marketing shtick. Or like, in these trying times, we love you so much and we believe that we used to shop our products. It's for the good of the world. And I was just. I didn't like it. I was not impressed. And I would ask myself, it's when people talk about change or they talk about making a difference or doing good, how are we defining that? Like, people talk impact all the time. Very rarely will they follow it up with a workable definition of what impact is. And impact is simply, it's the net positive change rendered as a direct and material result of your actions. So if you get an input, an action, you should get a specific reaction or outcome that you can measure, that you can quantify, that you can predict, right? That you can build a model that says, okay, if I am investing X number of hours at this much money, this much capital, this much this, I should expect this to be the result. And I wasn't seeing that. And I took a while to find a community of practitioners that were in this space of it's called IMM Impact Management and Measurement, right? People who are actually do things like an SROI analysis, like social return on investment analysis, who are applying global best practices or accounting standards for how we account for social value, how we, how we build up models that actually give us Like a predictive analysis of how things get done for real. So now I'm also a board member at Social Value International's US branch. So Social Value International is like 60 member countries that used to be the SROI network 20 years ago, but there's all these organizations globally that, that work together with the UN Sustainability Sustainable Development Goals. There's Global Impact Investing Network, which is gin. There's the impact management projects. There's a lot of academic, nonprofit, NGO institutions, like large institutions, investors, foundations that are all engaged in this work of furthering best practice, identifying like global reporting initiatives. So it's like there's so many now at this point. There's ifrs, there's, there's like SASB and IASB that have their own sustainability accounting standards. Right. So that, that was the area I wanted to play in. And for me what was cool is that because of my entertainment background, my background working with creatives, with producing, with creating content that has a lot of impact on people that like grabs people and grabs attention. That was excellent because I could marry that background with this new very academic work that I was doing. And I've got two master's degrees under my belt. I've got an MBA and I've also got the Master's of science. So this also allowed me this pivot to pursue my more academic inclinations. Anyway, so basically by starting my own thing and being my own boss, it gave me the opportunity to take all the things that I've always been interested in and always cared about and always wanted to see wedded together and now I get to do that. My, my kind of slogan is I'm approaching change at the intersection of cause, culture and capital. So how do we marry those concepts together? How do we leverage capital and how do we influence culture to further a cause? How do these things work together? Like these three Cs of change making for me and that's been like a really cool journey. So I'm going into like my 5th year company and right now I'm working on a very large, my largest project yet, which is an international collaboration and executive producing one of, one of the largest non dilutive funding events on the African continent, specifically in Ethiopia. So we're, I'm executive producing the Great Rift Valley Innovation Summit, co leading that and that's going to be next year. So I'll be traveling to Africa for the first time, be watching like a live pitch competition. We're partnered with the un, the United Nations Development Program for this initiative and a bunch of other public and Private sector institutions, large institutions to deliver money right into the hands of Ethiopian founders who are doing great work in healthcare and education, agriculture, and making a big difference in that country where the median age by the way, is like 90. Innovates, like a very. This very hungry, like very innovative. A lot of things going on. So I'm excited about what I'm doing in that space.

[Vince Chen]

Wow. Honestly, I was just so drawn in by what you said. I kind of zoned out from coming up with more questions because I was so absorbed in your story. And while listening, someone instantly came to my mind. She is a former guest, actually one of the guests in season one, a founding guest, my classmate from Chicago, Booth. She is from France, but currently in Senegal, Africa, serving as the technical advisor to the government, working on innovation and economic development. I feel like the two of you might really connect. You mentioned Africa, you mentioned Ethiopia being your biggest project yet. Who knows, maybe Senegal could be your next destination.

[Sienna Jackson]

Hey, I'll take any excuse to hop on plane and go somewhere new. It's really cool because I think that speaks to just the global nature of this work, which is really great because it's such a large community of people that are so smart and so multi talented and everyone is really motivated to make a difference, to make a meaningful, tangible impact. I often say to people like I'll point out to my peers, every problem that we have in the world is a man made problem. Which means that there's a man made solution for every problem by that same token, right? So like we can we understand the contours of why things are the way they are, or if something is wrong, that something's amiss, we can understand the landscape and then build tactics and strategies and put things into operation that can make a difference. And part of my job is to explicate first of all the vision of where we want to go and then the tangibles of how we get there, which is always. It's a lot of project management work I have to do at the end of the day. It's a lot of ops, it's a lot of operations.

[Vince Chen]

Actually you started this back in 20, 25 years now, and so much has changed since then. The worrying, the symptoms, and even the conversations we're having around Impact. As you've grown your business and expanded your advisory work, I'm curious, what barriers have you seen or experienced along the way? Impact is a noble cause, no doubt about it, and I imagine a lot of people support it in theory. But in practice, what gets in the way is it mindset. I don't think money or technology are the biggest barriers. Those tend to be solvable. I'd love to hear from you, to learn from you. What real challenges have you run into and how did you navigate or solve them.

[Sienna Jackson]

Yeah, I think the big thing that I noticed right out the gate was a lack of professional, peer community and network.

[AT&T Business]

And now a next level moment from ATT Business. Say you've sent out a gigantic shipment of pillows and they need to be there in time for International Sleep Day. You've got at and T5G so you're fully confident, but the vendor isn't responding and International Sleep Day is tomorrow. Luckily, AT&T5G lets you deal with any issues with ease so the pillows will get delivered and everyone can sleep soundly, especially you. AT&T5G requires a compatible plan and device coverage not available everywhere. Learn [e-mail] 5G Network.

[USAA]

USAA knows dynamic duos can save the day like superheroes and sidekicks or auto and home insurance. With USAA you can bundle your auto and home and save up to 10%. Tap the banner to learn more and get a'@usaa.com bundle restrictions apply.

[HubSpot]

It's impossible to find more time in the day until now. With HubSpot's suite of AI powered tools, you can get more done way faster, speed up your lead generation and create attention grabbing, lead driving, quota crushing campaigns in an instant, which will give you more than enough time to listen to podcasts like this one. HubSpot Impossible Growth made Impossibly easy. Get started [e-mail] AI look around.

[Autotrader]

You can find cars like these on Autotrader. New cars, used cars, electric cars, maybe even flyin cars. Okay, no flying cars, but as soon as they get invented, they'll be on Autotrader. Just you wait.

[Amazon Pharmacy]

Autotrader Building a business may feel like a big jump, but On Deck small business loans can help keep you afloat. With lines of credit up to $100,000 and term loans up to $250,000, OnDeck lets you choose the loan that's right for your business. As a top rated online small business lender, OnDeck's team of loan advisors can help you find the right business loan to fit your needs. Visit on ondeck.com for more information. Depending on certain loan attributes, your business loan may be issued by On Deck or Celtic Bank. On Deck does not lend in North Dakota, all loans and amounts subject to lender approval.

[Sienna Jackson]

Really what we're talking about is the whole global landscape of like philanthropy, right? When we're thinking about like corporate social responsibility or ESG or evaluation and measurement, all these overlapping things, it's a lot of different skill sets that come to bear in this sort of work. If I'm an accountant, I'm going to be a, I'm going to be a cpa, I'm going to join my national association of whatever, right? If I'm a lawyer, I have to pass the bar exam and have my jd, I join my local bar association, right? You don't have that similar clear cut career progression for people who want impact. So there's a lot of work that needs to be done in terms of professionalizing the industry, at least here in the United States. So part of what I am working on in my leadership role at Social Value is creating an industry survey. So again, this entertainment thing, I was like, I told my ears there, I was like, in the entertainment industry we have, we have industry surveys where we know how many people are employed in the entertainment industry, know how many, like above and below the line, we know what people's salaries are, we know what titles are, we know what roles are, we know who is doing what and what qualifications they need to succeed. We don't really have something equivalent for our industry, our discipline and we need that. That's something I'm going to be rolling out sometime in the new year. I was lucky because I had the initiative to hunt people down. I knew I needed peers, I needed colleagues and I needed people who were in this space longer than me and that were more knowledgeable and I took the time to hunt them down. And I think that's something that maybe not everyone getting their start has the benefit of that. So usually when I talk to young people, because I do a lot of talks, I do a lot of public speaking, I teach workshops. When I talk to young change practitioners, people who want to work in impact or sustainability and have no idea how to get started, I usually come at them with a list. Get on this newsletter, get on that newsletter again. Here's this party, this event series that happens or this networking session that happens in la. So but when it comes to impact sustainability space here in Los Angeles, I feel like I have good handle on that. The thing that I will tell people all the time is you can't silo yourself. I think the one of the big challenges I see in my space, especially when I like dealing with my clients, is like siloing. Like the left hand doesn't know what the right hand is doing or communicating to each other. And especially if it's cross sector, if you have one party here who's like, in the nonprofit world, they really only know how to talk to other nonprofit people. But you have someone over here who's either private sector, maybe they work for a big firm and they only know their industry, but they want to make a difference on this problem. How do you create a bridge between these two poles? Because of my background and the diversity of experience I have, I can speak to each party in their own language and draw them together and build a coalition. So I think that skill set of being able to speak to people in their language, put together coalitions that are intersectional, that bring stakeholders from very different backgrounds together and get them on the same page, and then have a goal and guiding them to achieving that goal. That's my superpower in what I do. And that takes just time and trying and thinking about. Always. You have a goal, have that vision in your head of what it is you're trying to achieve in the world, and then work backwards from there. But ask yourself, like, what is it you really want to see happen? And then say, okay, how do I make that happen? And who do I need on my side to get to this objective?

[Vince Chen]

Oh, it sounds like the missing pieces aren't simply resources or funding. It's really about people, talent, and the lack of real coordination. Community, coalition, like you said, humility, all of that ties directly back to your mission, pursuing change at the intersection of culture, capital, and cause. I think we've covered some incredibly powerful ground today. But before we close, any final thoughts you'd like to share? Maybe something we didn't get to or message you want to leave with the audience, whether it's about impact, AI or something else close to your heart.

[Sienna Jackson]

I think for anybody in your audience that wants to use their work to make a difference in the world, who wants to do good, understand that every single person has their own unique way of doing good in the world. You have something unique to offer that's entirely yours. It's kind of going back to the idea about art as self expression. There's something in you, something unique about your background or your experience, or your point of view, or your skill sets or your talents that you can uniquely apply. So if you look out at the world and you see a problem that really bothers you, first ask yourself, where are the helpers? Who are the people who are already doing good work in this area, who are addressing this problem? And then how can I uniquely contribute to that work? How can I roll up my sleeves and help the helpers, because that's what I find usually yields the most immediate results. And it also helps if you feel like overwhelmed with the world and overwhelmed with all the things that are going on and you say, oh, how can I possibly make a difference all on my own? You can't look for the helpers and help them and then you won't be alone and you'll also be doing a lot of good at the same time.

[Vince Chen]

That's such a powerful reminder. And honestly, I needed to hear it too. I'm going through my own transition at the moment. There are surely things that bother me, challenge me. But like you said, the key is to look at who's already working on those problems I care about and then ask how can I add to that? Where can my skill, my background, or even my voice help amplify that problem or solution? And from there it becomes about execution, collecting the right data, tracking what matters, making smarter decisions, measuring your risks and accelerating both the scale and depth of impact over time.

[Sienna Jackson]

Yeah, exactly. Yeah. I think even with the show like that, and you've already heard me tell you, I think even a show like this, you're connecting to people who might not otherwise get the chance to hear this certain perspective. Or maybe they they're in their own career journey and are really struggling or they're really seeking something. So if there again, it's like everyone has their own special and unique way of doing good.

[Vince Chen]

And that brings our series too close. Sienna's journey is proof that change doesn't start with the loudest voice in the room. It starts with clarity, curiosity and the courage to take the first step. Whether she's guiding companies through complex decisions or helping entrepreneurs and founders across Africa scale their ideas, she reminds us every man made problem has a man made solution. And often the most powerful thing you can do is help the helpers. 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 Chan, your ambitious human host. Until next time, take care.

[Bluehost]

I'm not exactly a tech genius, but I knew one thing for sure. If I wanted my small business to crush it, I needed a website that worked like a pro. And I needed it yesterday. Lucky for me, bluehost made it ridiculously easy. With their AI design tools, building my website was a walk in the park. I could customize, optimize and monetize everything exactly how I wanted. In just a few minutes I had a secure site up and running. I couldn't believe how straightforward it was and getting found online. Bluehost helped me with that too. I perfected my keywords and meta descriptions with their search engine tools. The AI even gave me suggestions to improve my pages. Now I can sit back, relax and focus on my customers while my website continues to rank higher and higher on Google with their 30 day money back guarantee. I wasn't worried about taking the plunge. And now I'm so glad I did. Head over to bluehost.com and build something special today.

[AT&T Business]

And now a next level moment from ATT Business. Say you've sent out a gigantic shipment of pillows and they need to be there in time for International Sleep Day. You've got at and T5G so you're fully confident, but the vendor isn't responding. And International Sleep Day is tomorrow. Luckily, AT&T5G lets you deal with any issues with ease so the pillows will get delivered and everyone can sleep soundly, especially you. ATT 5G requires a compatible plan and device coverage not available everywhere. Learn [e-mail] 5G Network.

[Sienna Jackson]

How many discounts does USAA Auto Insurance offer? Too many to say here. Multi vehicle Discount Safe Driver Discount New vehicle Discount Storage Discount Legacy how many discounts will you stack up? Tap the banner or visit usaa.com autodiscounts restrictions apply.