Alyssa Cutright: “Digital first approach to ecommerce”

Digital first approach to ecommerce — Retailers adapting to ecommerce also need to ensure they’re still accessible for all consumers. By offering global payment options based on geographic demand, retailers can cater and appeal to a wider array of customers within the U.S. and beyond, and potentially increase their bottom lines. As part of our series about the […]

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Digital first approach to ecommerce — Retailers adapting to ecommerce also need to ensure they’re still accessible for all consumers. By offering global payment options based on geographic demand, retailers can cater and appeal to a wider array of customers within the U.S. and beyond, and potentially increase their bottom lines.

As part of our series about the future of retail, I had the pleasure of interviewing Alyssa Cutright, eBay’s Vice President of Global Payments, leading eBay’s global strategy and operations for payments, risk and billing. Alyssa joined eBay in 2016 with a proven track record of more than 20 years in industry leadership roles. Most recently responsible for overall operations at Plastiq, Alyssa also led Square’s International expansion as well as spent 12 years at PayPal in a variety of critical roles, including Financial Services (Core Payments), Risk Management, and the North America Product teams. Earlier in her career, Alyssa spent 10 years at Wells Fargo Bank.

Alyssa is a graduate of U.C. Santa Barbara.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

I started my career in commercial banking at Wells Fargo where I worked my way through the ranks and started moving more into payments. I was interested in the digitization of banking and payments, and seeing what was coming out of Silicon Valley at that time, I realized I had an opportunity to pivot my career and break into that space. So I decided to join, which was Elon Musk’s startup that had less than 100 employees at the time.

From there, we merged with PayPal and I started building out payments around the globe. I spent twelve years working in the global expansion of payments and later in risk management. After PayPal, I moved to Square to develop and lead international strategy and expanded Square into Canada and Japan before joining another startup called Plastiq. In 2016, I joined eBay to lead, build and develop our payments strategy.

Can you share the most interesting story that happened to you since you started your career?

One story that comes to mind is when I made the decision to join Plastiq to help them scale. At that point in my career, I never thought I would go work for two founders who had just graduated college, but I really believed in what they were doing and saw so much opportunity — both for the company and in their people. I could see how they understood the intricacies of payments that many seasoned professionals didn’t. Payments can be a vague space and they understood how to navigate the space, seep through the tiniest cracks and challenge the status quo. They demonstrated the behaviors of entrepreneurs that persevere and succeed, which was exciting, challenging and inspiring. The chance to take the areas where I excel — building and scaling — and pair that with their passion and relentless enthusiasm was one of the highlights of my career.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson or take away you learned from that?

I don’t have any funny mistakes that stand out, however, I can say that I intentionally treat any mistake — big or small — as an opportunity to learn. It’s a lesson that I continue to apply to my own personal development, and I encourage my teams to do the same with mistakes they may make in their work.

None of us are able to achieve success without some help along the way. Is there a particular person to whom you are grateful, who helped get you to where you are? Can you share a story?

I think back to my banking days at Wells Fargo and I think about Caryl Athanasiu, who at the time was a senior executive in the commercial bank. She was really hard on me and very direct — she pushed me. She allowed me to develop, took bets on me, and really gave me opportunities to grow.

I also think about Scott Thompson from my PayPal days, who was our CTO at the time. He was looking for a leader in risk management and he, again, took a bet on me to turn around the risk team with his unwavering support. At that time, I had some knowledge around risk, but I didn’t really have a traditional risk background.

  1. How have you used your success to bring goodness to the world?

I would say it’s two fold. First, I’ve been very fortunate to work for companies like eBay that have real purpose in enabling small businesses to get up and running and to grow. It’s really special to know that the work we do each day helps others pursue their dreams and support their families. In addition, the companies I’ve been fortunate to work for really invest in their people and that has not only allowed me to grow both personally and professionally, but to develop others coming up around me. I’m a firm believer that you don’t have to only hire people that have years and years of experience, but to also look for a set of behaviors, including curiosity, drive and accountability, that contribute to successful leaders and teams. And then you learn as you go.

Are you working on any new exciting projects now? How do you think that might help people?

Right now, we are working on expanding and growing our managed payments program at eBay and we basically operate as a start-up inside the company. This is a really exciting project for me because it’s a program that is bringing a win-win solution to all. Through managed payments, eBay is able to better support our sellers and buyers around the world — we are making ecommerce easier and more user friendly. Our buyers have more flexibility in how they choose to pay and sellers can manage sales and collect their payments all on one platform, simplifying how they manage their business on eBay.

Advice to others

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

This is a tough question, because I do believe it’s unique to each individual. Work-life balance is very personal and you have to be authentic to what feels right for you. So in terms of what tips would I give? Authenticity is key. Knowing what does and doesn’t work for you and sticking to that is extremely important.

Couple authenticity with the importance of persistence, curiosity, and constantly asking questions. There will always be roadblocks, but not being afraid to ask questions during those roadblock moments will challenge the status quo and get people to really think creatively. One thing that I’ve learned in my career is the combination of human ingenuity and creativity is often what makes a lot of the impossible possible.

The so-called “Retail Apocalypse” has been going on for about a decade. While many retailers are struggling, some retailers, like Lululemon, Kroger, and Costco are quite profitable. Can you share a few lessons that other retailers can learn from the success of profitable retailers?

I’m a big believer of when you find yourself stuck or not sure which way to move forward, focus on being customer led. It’s so important for retailers to really get to know their customer, and I always say walk a mile in your customers’ shoes. These larger, highly successful retailers have gained a solid understanding of who their customers are, how they use their products or services, and understand the challenges they are facing.

Looking at this from a payments perspective, it’s common for companies to go to their customers and ask them what their top pain points are around payments. Then you take what they give you and work that into your overall strategy, and then realize you are not seeing the expected uptake. At the end of the day, for many customers and in our case sellers at eBay, payments are often not their biggest pain points. They are about higher sales conversion, more customers, more efficient operations. You really need to understand how your users run their small business and then use your expertise to understand what you might be able to do to help them in ways that might not otherwise be obvious. It’s important for smaller or struggling retailers to listen to customers and use those insights, combined with their expertise, to improve their overall product or service.

Amazon is going to exert pressure on all of retail for the foreseeable future. New Direct-To-Consumer companies based in China are emerging that offer prices that are much cheaper than US and European brands. What would you advise to retail companies and e-commerce companies, for them to be successful in the face of such strong competition?

This goes back to the importance of really knowing your customers. With the many different players in the market today, it’s about service differentiation. It might mean some customers will choose to seek the lowest cost out there, so you may lean into a different customer base who are looking for more flexibility in returns, the ability to pay over time, etc. Remember, it’s all about knowing your customer — what they want and need, and finding unique ways to bring them value and drive loyalty.

Industry Outlook

The Pandemic has changed many aspects of all of our lives. One of them is the fact that so many of us have gotten used to shopping almost exclusively online. Can you share five examples of different ideas that large retail outlets are implementing to adapt to the new realities created by the Pandemic?

  • Digital first approach to ecommerce — Retailers adapting to ecommerce also need to ensure they’re still accessible for all consumers. By offering global payment options based on geographic demand, retailers can cater and appeal to a wider array of customers within the U.S. and beyond, and potentially increase their bottom lines.
  • Mobile payments — A recent study done by PYMNTS revealed that consumers are primarily using smartphones as financial management tools, with more than 90% of Gen Z consumers having downloaded card apps. Retailers such as Walmart and Target have become more reliant on mobile wallet support, and buy online, pick up in store (BOPIS) options.
  • Flexible payment options — When platforms and sellers are able to provide a wider range of payment methods, it keeps the marketplace consumer interest. This includes options like credit cards, debit cards, gift cards and e-wallets, and these will come out on top.
  • Contactless payments — COVID has highlighted the popularity of contactless payments, and has accelerated innovation in the tech payments space. The ability for retailers to grow with payment options brings added value, and keeps retailers competitive in the space.
  • Delivery of payments — There’s been a shift in how we’ve seen retailers deliver their payment options to customers, for example, the use of QR codes. What’s interesting here is that this technology isn’t necessarily new, but we’re seeing it pick back up again as a result of the pandemic.

In your opinion, will retail stores or malls continue to exist? How would you articulate the role of physical retail spaces at a time when online commerce platforms like Amazon Prime or Instacart can deliver the same day or the next day?

I do think we will continue to see some sort of a physical mall and shopping space amidst the rise in consumers shopping online. Humans are inherently social and shopping is still a social activity that consumers aren’t going to just give up. While I do think these physical spaces will exist, that’s not to say they won’t evolve from how they have looked, historically. I see necessity items as something that will increasingly move online, where physical retail stores will largely shift to prioritize the personalized customer experience.

You are a person of great influence — if you could start a movement that would bring the most amount of good to the most amount of people, what would that be?

If I could start my own movement I would want to focus on equality and open access for all. When everyone has equal access and equal opportunity, it breaks down boundaries, opens up possibilities, and allows for growth opportunities on so many levels.

How can our readers further follow your work?

Feel free to follow me on LinkedIn here. You can also read more about eBay’s managed payments journey on

This was very inspiring. Thank you so much for joining us!

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