Happy Money CEO Jeff Winner on fintech and API technologies

Happy Money's dynamic CEO, Jeff Winner, has worked with Twitter, Stripe and Goldman Sachs. Now he's heading up a new fintech with a mission in CX services

As the CEO of Happy Money, Jeff Winner has enjoyed a varied career in fintech, working with some of the world's most dynamic companies. His expertise in technology and API development has enabled him to build a career path that has been rooted in his passion for innovation. Today, he heads up the Colorado-based fintech Happy Money - which is famous for its fintech building tools and services that are geared towards generating human happiness.

In short, Happy Money is a leading facilitator of unsecured personal loans in partnership with community-focused credit unions. Leveraging its human-centric, science-backed approach to finance, the company has already helped members pay off over $3bn in debt – facilitating $1bn in loans in 2020 alone. Continuing its innovation and growth trajectory, Happy Money is also developing new programs and technology designed to help consumers have a happier relationship with money.  We caught up with Winner for a chat about what motivates him, and why fintech and financial contentment for customers, is now his mission. 

Q: What made you want to get involved in fintech?

So many things. From my time at tech companies such as Twitter and Stripe, to my experience at Goldman Sachs, I have built a career that unites the benefits of Silicon Valley and Wall Street – creating a unique blend that perfectly positions me to lead Happy Money.  As CTO for Marcus, Goldman Sachs' Consumer Business, I led the development of the Apple Card and pioneered the first cloud-based Goldman Sachs product.

Much of my career has been working to connect ‘fin’ and ‘tech’, and Happy Money offered an innovative, mission-driven approach to fintech that I hadn’t seen before. I was intrigued by Happy Money’s mission to help people use money as a tool for happiness. And I recognised the opportunity that Happy Money presents to its capital partners – primarily credit unions – in terms of helping them digitize their banking solutions. I knew that with over 15 years of experience building APIs, I could successfully lead the Happy Money team in standing up the industry’s first E2E API for unsecured lending.

Q: In your view, how are relationships and partnerships among the most valuable assets for fintech companies? 

For many fintechs, partners are how their products and services get to market at scale. It’s a symbiotic relationship. When the partners do well, the fintechs providing the products, services, and platforms that enable their success do well too. For Happy Money, this comes to life through our relationships with our capital partners – primarily Credit Unions. These Credit Unions are nonprofit organisations with a charter to benefit their members, so our missions are very much aligned. High-quality lending products are an important part of a member's financial life. We can work with our partners to provide that at scale. 

Q: What is the greatest lesson you've learned in your career as a fintech executive?

The greatest lesson I’ve learned is to always challenge the status quo and encourage teams to do the same. It’s vital that we apply rigorous thinking to our work and embrace a growth mindset – staying curious and open to new ideas. Additionally, from my years of fundraising at Stripe, Twitter, and now Happy Money I've learned that investors are not afraid to let you know what they think – and that is of huge value. Take the feedback, test, iterate, and learn.

Q: What are the most effective strategies for fintech firms to expand their businesses?

Operate with transparency and create psychological safety. It’s critical that leaders work to decrease organisational distance in their businesses. Great ideas can come from anywhere, so keep the lines of two-way communication open. Move with urgency and cultivate a culture of ownership and accountability. People steward their resources better and are quicker to address challenges when they’re empowered to operate as an owner. This is critical to business growth.

Adopt a test-and-learn methodology – especially in dynamic times like these. Embrace opportunities to challenge the status quo and make bold decisions. One of the best ways to do this is to operate like a lean startup, continuing to test, learn, and iterate. While it’s important to remain aware of the competitive landscape, don’t focus on your competitors. Rather, focus on the people you’re serving, the product you’re delivering, and how to make it consistently better over time. 

Q: What is the most interesting aspect of financial technology to you right now? And how do you think the industry will turn out by 2030?

In today's world of embedded finance, companies must go where the customers are instead of expecting them to come to your website – let alone a physical banking branch. APIs are already changing the way banking is done, and they’re poised to become the way financial institutions and customers interact. They will also help accelerate product innovation and create new distribution and revenue avenues for financial services firms. Compared with traditional point-to-point integrations, APIs are flexible and cost-efficient, and easy for consumers to operate. At the simplest level, APIs are black boxes, allowing companies to change what’s under the hood without the consumer ever knowing that anything has changed or having to lift a finger to reap the benefits of those changes. That simplicity and speed of innovation are the future.

Q: Please summarize your business life in three words.

Transparency, innovation, and growth

Q: What’s next for Happy Money in the coming three to five years?

We have our sights set on making Happy Money the go-to unsecured lending platform for Credit Unions and community banks. Embedded finance and APIs are the future of banking, and we’re investing in standing up an end-to-end (E2E) unsecured lending API that will enable us to deliver more value to our consumers and partners. Differentiated underwriting guidelines embedded in this platform will support our distinct point of view on lending – having consumers’ best interests at heart. Evaluating ability and intent to pay off debt allows us to offer consumers better pricing and provide access to people who might otherwise be missed by traditional methods for measuring creditworthiness alone.

Q: Last, what is the one thing you want everyone to know about Jeff Winner?

I am a perpetual learner – both in my personal and professional life. On the professional side, I’m honored to have recently stepped into the role of CEO of Happy Money, I continually learn by listening to our incredible talent. Personally, I’m upping my weight training regimen and hoping to get back into singing more this year.

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