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Welcome To Digital 2.0:
The Modern Digital Executive Interview Series.
Episode 11 / December 13, 2022
Digital 2.0 Episode 11:
Sameera Rao, CTO at Greenlight
In this episode, Sameera Rao, CTO at Greenlight talks about Greenlight has finding its way onto more than four million devices. And in only seven months, the company nearly doubled the unicorn valuation it received in a $215 million fundraise. What started as a small team has grown into an organization of 600 employees.
Digital 2.0 is an interview series dedicated to interviewing the best and brightest senior digital executives around the world that have taken a stance on the importance of Digital within their organizations and are helping everyone understand the role of technology in our everyday lives.
Episode 11 / December 13, 2022
Investing Is So Simple a Kid Can Do It, and Other Things I Learned from Greenlight CTO Sameera Rao


“If only I’d have started my 401(k) a decade ago.” Have you ever felt that pang of regret? If so, you’ll enjoy episode 11 of Digital 2.0 with special guest Sameera Rao.

Sameera doesn’t have a DeLorean time machine to transport you back so you can give your younger self a jump-start lesson in economics, but he may have the next best thing.

Sameera’s the Chief Technology Officer for Greenlight, an organization that flips common money and investment myths on their head by giving families a simple app to manage their finances and passively invest. It’s a brilliant app, and the numbers confirm it.

Currently valued at $2.3 billion, Greenlight has found its way onto more than four million devices. And in only seven months, the company nearly doubled the unicorn valuation it received in a $215 million fundraise. What started as a small team has grown into an organization of 600 employees.

During our 30-minute conversation, Sameera and I talked about how simple, user-friendly technology can eliminate barriers standing between families and steer children toward a strong economic future.

I also picked his brain on a range of topics, including Elon Musk, why he admires Microsoft and PayPal, and what it takes for organizations to drive innovation.

It was a fascinating discussion, and I’m pleased to share it with you.

Biggest Lessons Learned About Transforming Companies Digitally

Sameera has nearly 25 years of experience in the tech industry.

He’s served Bosch, GE, and Sabre as a software engineer and was the man behind the first web 2.0 version of the Yahoo! homepage. During his nine-year tenure with PayPal, he filled several roles, including VP and head of technology, VP of consumer energy, senior director, and global head of consumer engineering.

I wanted to know what two and a half decades have taught Sameera about transforming companies. Here’s what he said.

“When most people hear ‘innovation,’ they think about technology,” he says. “Technology helps, but don’t forget about people.”

Sameera spent nearly a decade with PayPal, and he’s still fond of the company’s people-first ethos.

“Many organizations give lip service to ‘leveling the playing field’ for consumers, yet they prey on insufficiencies in the market in a way that does not benefit customers,” he says. But that’s not the PayPal way.

In the beginning, PayPal steered customers to its low-cost instrument, and while it wasn’t what customers wanted to use, it was the highest-margin project for the company. But that changed.

Why? Because PayPal maintained its commitment to championing customers and building an enduring company over the long haul. So PayPal started allowing users to choose the instrument they want to pay with.

Guess what happened? Initially, PayPal’s stock dropped 9 percent.

Then, two years later, PayPal added 70 million incremental customers when their strategy went global. Next, transactions nearly doubled, and customer service calls dropped.

What does that mean? The strategy worked. Customers were happier, costs went down, people spent more, and engagement increased.

“PayPal took a gamble to preserve its ethics,” says Sameera. “They were willing to take a risk—at their own expense—to give consumers what they deserved, and they were rewarded for it.”

Tech organizations can be at the forefront of the tech movement. Yet Sameera argues that “if their product isn’t ethically produced and does not give everyone the opportunity to participate in the economy, I don’t see much nobility in the innovation.”

What Do Innovation, Transformation, and Modernization Mean to You?

I wanted to know what “innovation,” “transformation,” and “modernization” mean to a guy who’s spent 25 years in the tech industry. But Sameera’s answer has little to do with technology.

“I’ve seen—and helped—big organizations transform, and those that succeed generally share the same principles,” he says. “They listen to people, hold their hands along the journey, and elicit change by giving context, not commands.”

When you adopt this set of principles, you increase the odds of securing the cross-organizational buy-in you need to make lasting change. For Sameera, that’s the path to innovation.


Sameera grew up in India, and while his father kept the engine of Sameera’s middle-class family running, he never talked about investing.

Sameera believes that most kids share his experience.

“Most of us don’t even think about investing in a 401(k) until we’re in our 30s or 40s,” he says. “We may take an economics course in school, but few of us know how finances really work until much later on.”

And that’s the idea behind Greenlight. “I want to give families what I didn’t have—a simple app that empowers parents to raise financially-literate kids.”

How? By giving them a simple, user-friendly app that controls kids’ spending, manages their chores, automates allowances, and helps them passively invest.

There’s a common belief that you need a stash of money to save or invest, but Sameera’s daily mission is to dispel the myth that investing is for the one percent.

“Our parent-users have access to a family cash card that gives you three percent unlimited cash back on purchases. That money just comes off what you’re already spending and is rechanneled into a new investment vehicle,” he says. “The entire process is automated, so parents invest without thinking about it.”

So rather than berate yourself for not starting your 401(k) years ago, Greenlight gives families the tools they need to invest—without feeling like they’re sacrificing.

Maintaining Pace in the Digital Age: Companies That Are Surprising

I wanted to know what Sameera believes will determine which organizations will be around in the next decade. He argues that it won’t necessarily be those preoccupied with technology.

“I want to be on the bleeding edge of the tech movement, but if that technology doesn’t better serve our customers, it won’t help us,” he says. So while organizations must be technologically nimble, Sameera argues that it’s just as important for organizations to “hold their customers’ hands and lead them with empathy and compassion.”

We’ve all heard failed executives proclaim, “We did everything right, but somehow we still failed.”

Why? “Chances are these companies weren’t listening to customers, evolving, and leadership wasn’t bold and self-aware,” he says.

The last two pieces—being self-aware and bold—are especially important.

The challenge of being self-aware is that we all have blind spots. We don’t know what we don’t know about ourselves. That’s why we must surround ourselves with people we trust, not people who agree with us.

Being bold is also a challenge, especially when you’re successful and want to protect your legacy.

But look at companies like Microsoft, Apple, and even Tesla.

“I admire Microsoft for the same reasons I do Apple,” Sameera says. “Both companies could have rested on the success of their models, cashed in, and coasted. Neither have. Every year, they push boundaries and try something new.”

The same goes for Tesla. “How many times have you thought, ‘Oh, Tesla’s playing with fire; they’re on the brink. It’s over,’” Sameera says. “Yet, they still push forward.”

“These are three very different organizations, but they all have one thing in common: They STILL have the stomach for risk and ride the knife’s edge of risk and reward,” he says.

Any company aiming to be around in a decade can learn a valuable lesson from these Big Three.

Digital 2.0 Hot Seat: Real, Hype, or WTF

I closed our conversation with a series of rapid-fire questions covering four of my favorite topics: the Metaverse, crypto, Elon Musk, and remote/hybrid work.

Are they real, hype, or do they just make you scratch your head and say, “WTF?” Here’s what Sameera had to say:

The Metaverse:

“I might eat my words three years down the road, butI’d say the Metaverse is a mix of hype and ‘WTF?’”


“Crypto’s real, but a lot needs to happen—especially in the final stages—to connect it with banks. That said, the blockchain tech behind it is all there.”

Elon Musk:

Musk plays on the edge, but he’s definitely real.

Remote/Hybrid Work:

Very real. Remote makes it more challenging to establish camaraderie and teamwork, but the benefits are undeniable. Organizations just need to keep adapting and figure out how to do remote/hybrid well.

Thank you for a fascinating interview, Sameera!

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