Chief Change Officer - #416 Sienna Jackson: Culture, Capital, and the Courage to Start Young — Part Two

Episode Date: June 16, 2025

Sienna Jackson, the CEO of Nortera.io, walks us through her unexpected shift from entertainment executive to impact strategist. In Part Two, Sienna Jackson dives deeper into the business of social impact—from why she walked away from Hollywood to how she’s now helping build one of Africa’s largest funding summits. She explains how impact is more than a buzzword—it’s a measurable, strategic discipline. Sienna shares how to bridge silos, build coalitions, and roll up your sleeves to help the helpers. From the boardroom to Ethiopia, she shows that real change isn’t about ego or noise—it’s about clarity, community, and execution.Key Highlights of Our Interview:The Off-Ramp to Impact“I didn’t have a master plan. I just started doing small things—bought a domain, formed an LLC, sent one email: ‘I’m doing social impact now.’ That was the pivot.”You Can’t Improve What You Don’t Measure“Impact is the net positive change rendered as a direct and material result of your actions. If you can’t model it, predict it, or quantify it—it’s just branding.”Culture, Cause, Capital“My work lives at the intersection of culture, cause, and capital. You need all three to drive sustainable, global change.”Building a Real Profession“We don’t have a bar association or CPA license for impact work. That’s a problem. I’m creating a survey to start defining our industry.”Don’t Silo—Build Coalitions“You have to speak multiple professional languages. That’s how you bring nonprofit leaders and private sector players into the same room—and actually get something done.”Help the Helpers“If you feel overwhelmed, find the people already solving the problem—and ask how you can contribute. That’s how real change starts.”___________________________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.20 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>180,000+ are outgrowing. Act Today.<<<

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Oshul 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. 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? We'll put that, we'll separate that into two buckets. So like when I was in 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 of 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.

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 is gonna become the new cable. We're gonna wanna cut the cord, streaming, they're gonna 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, you need to figure out what you wanna do with your life and you've gotta 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 social 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 on a lot of different pies, and I had relationships and networks outside of the entertainment industries. People already knew 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 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 asked myself, when people talk about change, or they talk about making a difference or doing good, how are we defining that? 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 actually do things like an SROI analysis, like social and investment analysis,

who are applying global best practices or accounting standards for how we account for social value, how we build up models that actually give us 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 work together with the UN sustainability, sustainable development goals.

There's Global Impact Investing Network, which is JIN. 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 global reporting initiatives. So it's like, there's so many now at this point. There's IFRS, there's like SASB and IASB that have their own sustainability accounting standards, right? So 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 thought two master's degrees under my belt have been an MBA and I've also got a master's in 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 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 painstaking for me. And that's been like a really cool journey. So now I'm going into like my fifth year at Anthony. And right now I'm working on a very large, my largest project yet,

which is an international collaboration and the executive producing one of the largest non-dilutive funding events on the African continent, specifically in Ethiopia. So I'm executive producing the Great Raffaeli Innovation Summit, co-leading that. And that's going to be next year. So I'll be traveling to Africa for the first time.

I'll 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. Wow. Honestly, I was just so drawn in by what you said. I kind of zoomed 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. Hey, I'll take any excuse to hawk on a 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, is 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 wanna 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 actually. You started this back in 2020. Five 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? Yeah, I think the big thing that I noticed right out the gate was a lack of professional peer community and network. Really what we're talking about is the whole global landscape of philanthropy. When we're thinking about 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 CPA. I'm going to join my national association of whatever. If I'm a lawyer, I have to pass the bar exam, I have to have my JD. I join my local bar association. You don't have that similar clear-cut career progression

for people who work in 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 told my peers there, I was like, in the entertainment industry, we have industry surveys where we know how many people are employed in the entertainment industry. We 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, cause 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, get here's this party, this event series that happens or this networking session that happens in LA. So when it comes to impacts 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 one of the big challenges I see in my space,

especially when I'm dealing with my clients, is 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 it. But ask yourself, like, what is it you really wanna 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? 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. Humility, coalition, like you said, humility, all of that ties directly back to your mission,

pursuing change at the intersection of culture, capital, and cause. capital, and cause. I think we've covered some incredibly powerful ground today. But before we close, any final thought 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. 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 skillsets 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'll 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'll, you won't be alone and you'll also be doing a lot of good at the same time.

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 skills, 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 death of impact over time. Yeah, exactly. Yeah, I think even with a show like that, and you've already heard me tell you, I think in a show like this, it's you're connecting to people who might not otherwise get the chance

to hear this certain perspective, or maybe they're in their own career journey and are really struggling or they're really seeking something. So if, again, it's like everyone has their own special and unique way of doing good. ["The Greatest Showman"] And that brings our series to a 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 Chen, your ambitious human host. Until next time, take care.