Dwolla’s Brady Harris Talks Leadership and Driving Value

Leadership and successful business ideas

MP recently sat down with Brady Harris, CEO of Dwolla. With over 20 years of experience in the payments industry, he joined Dwolla to help bring account-to-account payments to any industry. Prior to Dwolla, he was the President of Payscape and a member of the senior executive team, overseeing more than 1,000 employees between 13 global offices. In his 18+ year history of leadership in FinTech, Payments, and SaaS industries, including multiple successful private equity transactions, he’s been a part of really accelerating growth and successfully scaling start-up type businesses.
 

Dwolla CEO Brady Harris
Dwolla CEO Brady Harris / Photo courtesy of Brady Harris

MP: What is Dwolla, and how is it unique to other modern payment/fintech companies?

BH: Dwolla is a very modern, forward-thinking company full of team members from across the country who want nothing more than to change how the world moves money. Pretty simple right? It’s refreshing to be part of a group of committed individuals who genuinely want each of their team members to succeed and see the company flourish. And fortunately, we’re seeing this come to fruition. Those same team members are the ones building this world-class technology, supporting our innovative clients, and solving really complex problems.

What sets us apart from our competitors is our authentic approach to working with our clients and partners, rapid speed to market, faster payment options, and flexibility of our technology that supports more sophisticated use cases. We’re also focused on filling the need in the space between what has historically been cards on one side and ACH on the other.

How is Dwolla making employees’ lives better?

We know that our success is directly related to providing our employees with a positive, inclusive, and open culture. A few of the benefits we offer our employees include stock options giving ownership in building value, in addition to a 401K match, Health Savings Accounts, unlimited paid time off, and access to Headspace Plus. Additionally, we were very early adopters of a remote-first approach that encourages a positive work-life balance, giving team members the flexibility to work from our headquarters, by the beach, or from a home office. In addition to these types of benefits, anyone at Dwolla is accessible—there are no barriers to communication here. If you have a question for me, send me a Slack. Our COO Dave (Glaser) does coffee with every employee during their birthday month. We’re intentional about being transparent, accessible, and open to new ideas. We all have one goal here.

What are three obstacles you’ve faced while getting Dwolla to be a viable company?

  1. Meaningful innovation quickly. We’ve needed to move quickly not only to survive the COVID-19 pandemic but come out of it thriving. And that’s a credit to our team. My goal is to ensure Dwolla innovates in a unique way that continues to expand the payment landscape.
  1. Meaningful partnerships. As the payment landscape evolves, forming impactful connections where each partner is adding value and creating a cohesive ecosystem is crucial.
  1. Expanding our international footprint. Navigating the regulations that vary by industry and country is a deeply intricate process that needs to be done right. Dwolla is committed to providing payment options for our customers that are fast, easy, and secure but also take the worry away from ensuring they’re done within the parameters of their business location. 

Do you believe there is some sort of pattern or formula to becoming a successful leader?

I believe there are a few key ingredients to becoming a successful leader. The first is knowing a business or industry from the ground up. For payments and fintech, I’ve always believed it was important to have the background knowledge of sales and the daily ‘on-the-ground’ details of the business, then working your way up. This ensures that when you reach the leadership level, you have intimate knowledge of how your products and services impact and function for those using them.

Second, I think any leader needs to be passionate not only about their business but also about the end-user. Passion is what drives successful leaders because you aren’t working to earn a paycheck, you’re leading because you care deeply about your business and customers. This passion is visible in your products and services and visible and inspiring for your employees. 

The last is that as a leader, you need to embrace the fact that you don’t and shouldn’t have all the answers. My job is to surround the business with the best and brightest, to hire smart and talented people, and empower them to make decisions. Delegating ownership and making sure employees are connected to their role is critical in building high-functioning teams and strong cultures. 

What are three pieces of advice you can share with people looking to become influential leaders in their businesses and why?

  1. Know the ‘why’ of what drives you to be a leader in your business. When you understand what drives you to lead, you will have a relatable connection that will make others want to follow you.
  1. The pathway to leadership isn’t linear. Don’t be discouraged if your path to leadership is taking turns that weren’t in your plan. You can pick-up a wealth of knowledge that will help you as a leader in positions that you didn’t think were on your track. 
  1. Think beyond the current landscape of your industry. Influential leaders use forward thinking to build for the future that’s to come, not just for where it is now. By seeing ahead of the curve, your leadership will have longevity.

What are your greatest fears as an entrepreneur, and how do you manage them?

  1. Ensuring that my ideas are solving problems in the most effective way possible. To do this, I think about the problem from every angle and listen to as many perspectives on it as I can find. When you can solve a problem in a way that benefits the maximum number of people, you’ve solved it correctly. 
  1. Keeping growth sustainable. Explosive growth is exciting, but to harness the power of that growth, I’m always making sure our bases are covered. Being prepared for the ability to scale rapidly gives you the room to do so without worry.
  1. Attracting the right partners. When you take the time to get to know your potential collaborators and what drives them, you forge the best partnerships. Ensuring values and goals are aligned, and not compromising on these is crucial for a successful partnership. 

How did you build a successful customer base at Dwolla?

We had a successful, loyal customer base long before I came to Dwolla—it’s my job to drive focus across Dwolla to get more of these types of businesses on the platform. And we’re doing that by catering to the customer’s needs in a way that gives them the freedom to focus on what they do best. We’ve made an incredibly complex process of navigating payment networks and regulations much simpler for our customers and their end-users. Additionally, providing dedicated client support makes for loyal customers who are benefitting from us in a way that allows them to grow, which in turn helps us grow. 

Is there anything else you’d like to share?

As a leader, you want to provide value to your customers and employees without being overbearing. Sharing your vision should motivate people rather than appear as a form of regulation or lecturing. Stay true to your vision. Putting vision and mission ahead of profits will keep you on track to create the solutions and attract the people that lead to the greatest accomplishments.