Dr. Melissa Sassi: From Wall Street to World Change

Not many of us can put on our resumés that we’ve done negotiations for NASCAR, given the Dalai Lama internet access, spent time on Hollywood movie sets, or helped provide thousands of devices for underserved students - but Dr. Melissa Sassi can.

She was born in small-town, Midwest America, a world away from the cosmopolitan hubs that would one day form the backdrop to her extraordinary career. In high school, her counselor predicted a future of mediocrity, failing to see the spark that lay beneath her restless exterior. But this veiled admonishment would inadvertently shape her future.

A critical intervention from her mother, who herself had navigated an incredible path from generational poverty and teenage motherhood to entrepreneurship, would change everything. A summer trip to Europe opened Melissa's eyes to the richness of global cultures and the beauty of difference. “For me it was like completing a puzzle. It was like skydiving into a place and having to figure out how you’re supposed to communicate. And when I came back I thought, whatever that is, I want to do that forever.”

Fast-forward to today, and Melissa is now an international force. She has carved a career at the bustling intersection of technology, education, economic development, and social impact, though as she points out, “tech is really at the intersection of every single industry.” Her journey has taken her to 60 countries, provided her with unique insights into achieving the Sustainable Development Goals, and offered her prestigious stints on Wall Street with BlackRock and Goldman Sachs.

Her doctoral thesis examined the role of digital inclusion in solving the SDGs - the bedrock of her passion. From her tenure at Microsoft, advocating for internet and energy access, to the founding of her youth-led nonprofit, MentorNations, that has taught tens of thousands of young changemakers to code across 12 countries, Melissa has been a tireless advocate for digital literacy: as the Chair of IEEE's Digital Skills and Readiness Working Group, she crafted the world's first definition for digital literacy, endorsed by the world's largest engineering organization.

This year, she’s launching Skills Hustle, an edtech start-up aimed at bridging the skills gap, her latest step in a career characterized by innovation and a refusal to accept the status quo.

And yet despite accomplishments so numerous they should be visible from space, Melissa is down-to-earth and extremely approachable. “I didn’t realise I was smart until I was around 35!” she says, laughing. She lights up when discussing the young people she mentors. She is giving with her insights, open about her obstacles - it’s clear that helping people drives her.

Melissa's story is a testament to the transformative power of passion, of unabashedly wanting to make a difference. She has gone on to shape the discourse around digital literacy, global development, and entrepreneurial success, embodying the extraordinary potential that lies within each of us, waiting to be unlocked - the moment we discover what really matters to us.

On board as a Venture Partner with us here at Machinelab, Melissa sat down to answer a few questions about her journey, her ambitions, and some absolutely jaw-dropping moments from her career.

I noticed that your career mainly unfolded in Marketing and then, interestingly, led to a VP position at Goldman Sachs. Tell me a bit about that. Was Marketing something you had a natural interest in?

I started my career in procurement and supply chain. I can’t say that I fit in very well, though it gave me a really good foundation in understanding finance, how to structure deals, and the cost pressures that a company might have. It also really helped me understand the elements that go into implementing a new product, a new service, a new solution that might be disruptive in the market.

But in my third job out of college, working in this procurement consultancy, they signed a big contract with Goodyear, the tire company. And they had this element of marketing, advertising, and media that they wanted us to look at. That was my first foray into how to manage creative agencies.

Fast forwarding a little bit, I had a wonderful opportunity to move into finance and banking. And it was right during the financial crisis, so while everyone was trying to leave banking, I jumped right in to building an internet bank. I joined GMAC [now GM Financial] and built what is now Ally Bank.

As I found that Goldman was going to start marketing, I thought, I could help with that. I looked to see who was the partner responsible for marketing at Goldman, so I reached out to her through a mutual connection, and we had coffee. I told her about my work, my expertise, and…what happened next, I’ve never seen anything like it.

This woman puts down her coffee, picks up the phone, she calls my boss, and says I’m not going to be coming to that job for a while, I’m being pulled to work in the executive office at Goldman. I was shocked. My boss had to say yes because she was a big partner in the firm, with one person between her and Lloyd Blankfein.

Shortly after, BlackRock heard about my work. $9 trillion of the world’s assets flow through BlackRock. And they hired me to come in and centralise the leadership.

That was when I realised I don’t know if I want to be in finance anymore. I want to make the world a better place. I want to do well, do good, make money, but I want to feel good. And I’m not sure that I feel so good. Was anything I was doing changing the world? No.

So one day I went in for my performance review and I resigned - and I moved to Nicaragua.

Wow. After that you were at Microsoft for 5 years, what was your experience like? Could you walk me through your career-path with them?

I started out my career at Microsoft in creative agency management. I managed the Hollywood relationships that Microsoft had globally. Our team created a campaign called Empowering Us All. And that led to the changing of Microsoft’s mission from a PC in every home to Empowering Every Person. We told a lot of stories about real people changing the world using tech. And I realised that I was sitting on the sidelines creating the operational engine for these inspiring individuals who were actually changing the world. And I realised, what was I doing?

I left my job way back when saying hey, I don’t want to work on Wall Street anymore, I want to change the world. And I realised I was still sitting on the sidelines.

I knew I needed to adjust my career. I knew I needed to pivot to something that involved evangelism, tech for good, social impact. My challenge was I didn’t have any experience in that area. So how do you take your experience from one vertical and put it into another?

If there was one memorable experience in your life/career, what was it and what made it stand out? What did you glean from it?

One day, I realised that my daughter didn’t have access to tech in her classroom. I ended up creating this amazing program that brought Microsoft together with HP. I got 400 laptops from Microsoft and HP, I found a bunch of different sponsors, and we took them all to North Africa - where my kids grew up.

When the trip wrapped up, I realised: I can’t do a job that doesn’t have this big world implication attached to it.

That ended up fuelling the research for my PhD. My research is on the digital inclusion of underserved and underrepresented communities and the tie it has to solving the most pressing issues of our time. That includes things like quality education, good health and well-being, gender inclusion, climate action - what you find in the SDGs.

As I was working on my research I discovered that there was no world standard for what it means to be digitally skilled. And so I thought, 'we need to have a world standard.'

How can we talk about the new literacy, meaning digital literacy and tech skills, if no one can really define what that means? How can you measure something if you can’t define it? You can’t tell whether you’re failing or succeeding if you don’t know how it’s defined.

I took it to the IEEE. It’s the largest engineering organisation on the planet, with 400,000 members worldwide. I took it to them and said, by 2030 we’re going to have an engineering shortage of 85 million jobs because people won’t have the necessary skills to take those jobs. That impacts revenue by 8.5 trillion dollars. It’s a big issue.

They liked it and they said we’ll do it - but we want you to be the chair. We spent a lot of time researching the different definitions, 100 different definitions and frameworks, and identified one that we felt would be the gold standard. So I was part of creating the first world standard for what it means to be digitally skilled and ready.

How did you adjust your career, and pivot to social impact?

As I was working on all this in my free time, I stumbled upon this cool team at Microsoft, an informal skunk works team trying to bring internet access to rural communities around the world and electrify villages. It sounded cool, so I joined them. We didn’t have approval so it was very underground, but we still ended up getting 100K from Brad Smith, Microsoft’s Chairman, to create a connectivity solution somewhere in the world. We chose Kenya.

Later on, Microsoft actually launched from the location that we built, and Satya’s book mentions our project twice.

So all of the devices that get given out by Microsoft anywhere in the world, I inspired that program. I’m proud to say I’m a hidden figure in that program, and that I revolutionised device-giving at Microsoft. I can also say that a project that I worked on brought the Dalai Lama Internet access!

I got to combine my skills with my passion, I kept knocking on doors and showing up and volunteering. What allowed me to move my career from one thing to another was volunteerism. I worked for free, so that I could achieve my dream of doing well while doing good.

Did the career shift begin at IBM? Startups and working with the youth seems like something you truly enjoy doing...

We need to have more young people with a seat at the table in key leadership conversations. It’s something that I not only talk about but I actually practice and I do.

I devote my life now to: 'how can I use whatever I have at my fingertips to enable the next generation of creators, makers, doers, technologists, politicians, and so on, to have a seat at the table right now?' It’s required of all of us - especially those of us in tech - to open up space, not compete, to elevate others.

We don’t have enough women and girls in tech. We don’t have enough venture capital flowing through to female founders. And a lot of that stuff starts at a young age. How do you make sure that women and girls can feel unapologetically them?

I’m very fortunate that I had the opportunity to create a program at IBM called IBM Z StudentX where I engaged with tens of thousands of young people every single year, I run coding camps, hackathons, and education challenges.

I also have my own startup, an edtech platform called SkillsHustle, and it’s all about preparing people for the future of work. It’s about democratising access to meaningful employment and entrepreneurship. And it’s inspiring life-long learning. I sitll consider myself a student, right now it’s informal education.

Where do you think startups fall short - especially new startups?

There are definitely some challenges that startup ecosystem has. But I want to look at it another way first.

VC funding is broken. The model just doesn’t make sense. You’ve got a VC that may look for 100 different investments. One of them is going to hit, and that’s where they make their money from. And less than 2% of funding goes to female founders.

But there’s been so many different studies that show when you have a diverse and inclusive board or executive committee, you make more money. The point is that when you have different perspectives and different voices, you’re able to better empathise with your audience. So that leads to better products, better decisions.

So where do startups fail? I think of this across different spectra. Do you have the right founding team? Do you have access to capital? Do you have product-market fit? Do you have the ability to scale? What’s your business model? Are you investment ready?

What's your big dream, your vision for the next few years?

I’ve spent a lot of time working on social impact endeavours, and I’m especially passionate about digital skills and tech entrepreneurship. One of my dreams is that we no longer hear people say, “I’m not technical. I’m not a techie.” I believe that tech skills have been taught all wrong for many of us - especially for women and girls. There are very interesting ways in which diverse and inclusive audiences can be brought into tech, whether that’s through innovation, entrepreneurship, creativity, the arts, culture.

Tech is really at the intersection of every single industry. And that’s not going to change, it’s going to exponentially grow. If we don’t have people who are competent engineers, data scientists, who are representative of different people around the world? We’re going to have biased products.

Think of all the challenges we’re going to have with AI. Can we trust the algorithms? If 6 white men in Silicon Valley create some platform is that platform going to truly incorporate the wants needs, aspirations, and pain points of a Nigerian woman in Lagos? Probably not.

I’m not saying every product starts out global - because it doesn’t. But how can you make sure you’re creating solutions that are reflective of your audience?

That’s one. The second one is I want to break the world of venture capital. I want to disrupt it. There is no reason why black founders and women founders should be receiving the amount of venture capital we receive, which is pretty much nothing.

Third - and this one is a bit crazy - I’d like to see a more decentralised world, more implementation and utilisation of blockchain technology. I would love to see a vastly different way of transacting, more utilisation of bitcoin and other types of tokens, and it’s very important that we don’t transition over to a central-bank-controlled digital currency. Our monetary system currently is not viable. We have this elite class of one percenters who have the majority of the world’s money. When you’ve got people all over the world working as hard as they possibly can, and they can’t even afford housing? Healthcare? Our system is broken. And it needs to be changed.

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Photo courtesy of: Dr. Melissa Sassi