Founded in 2020 by digital entrepreneur Matt Holme, YouPay aims to transform online shopping through shareable carts and enhanced digital payments. It blends interactive ecommerce with a financial focus on connecting people. In 2022, YouPay gained traction with Community Commerce and became a listed Shopify app, expanding its reach across 30 countries. It won the WeMoneys Best Innovation award and was a finalist for Merchant Payments Provider of the Year. YouPay’s app launch enabled sharing from top brands. In 2023, live gift card transactions with City Beach showcased YouPay’s ongoing innovation.
In a series of insightful interviews, Lachlan Grant, CEO of Vital Addition, engages with business leaders and CFOs, diving into the financial intricacies steering their enterprises. This conversation features Adrian Jenkinson, Chief Revenue Officer of YouPay, shedding light on the company’s evolution and unique value propositions.
What role do you see technology playing in the future of finance, and how are you preparing your team to embrace these changes?
YOUPAY
I think the biggest technology shift in the future of finance will come via AI. The challenge in financial management and analysis is that the lens on the business is always looking backward, and it doesn’t always bring the full business operating environment into view.
AI will deliver an enhanced ability to analyse the full set of business data (financial and non-financial) and create insights and recommendations in real-time. I believe this will have a significant impact on decision-making for any business.
Any step forward in delivering useful data that can support proactive decisioning will always be embraced by start-up teams and founders. The requirements around financial and business analysis are often a burden on teams, as they are focused on delivery, so analysis gets overlooked, which over time becomes a detriment to the business.
Can you walk us through what methods you apply when facing a particularly challenging financial decision? What steps do you take to arrive at your decision? What are the key factors you consider? What lessons have you learnt from these experiences?
Financial decisions for us are always based on ROI or R&D (that will deliver ROI). Do we get a measurable outcome from the investment, and does that give us the results or insights we need to identify product market fit, drive scale, or enhance UX (to deliver product market fit and scale)?
Financial decisions in start-ups are a balancing act between how much runway you have, what you need to spend to get to your next revenue milestone, and what’s critical to ensure you’re compliant and creating a sustainable and investable business.
As a leader, what key strategies have you implemented or do you plan to implement for navigating through a recession and keeping your organisation afloat, even thriving, during tough economic times?
The recent economic challenges have been a double-edged sword in many respects. The collective start-up ecosystem has seen a significant decline in investment, while at the same time we have seen an easing of the costs of quality staff due to many high-quality companies reducing their capacity.
This environment does bring a higher level of accountability and focus, and the real upside is that constraints force innovation. This has been our experience at YouPay. It’s the same with many of the brands we work with as they are now more open to embracing change and innovation.
When things are “good” there’s a bit of a “don’t mess with the winning formula” approach. However, tougher economic times bring the opportunity to innovate.
What were the career pathways that led you to the role of CRO at YouPay? And what do you consider to be the most important qualities for success in your role?
My early career was in banking and finance and I completed a degree in Accounting to give myself the most options for a future career path. I was lucky enough to be pushed into completing a further professional qualification as a chartered accountant through the CAANZ and ultimately was awarded Fellow status.
Throughout my career I’ve always been open to opportunities, and this has helped me round out my skillset as a true generalist across marketing, sales, operations and finance. My early career in the corporate world has been a great foundation for what I do today, and put me on the pathway into start-ups across the last 12 years. The key driver for me through all of this has been an unrelenting pursuit to solve problems, and being rewarded by helping other founders and their teams achieve their vision.
What do you look for when building a high-performing team?
Culture in a start-up is different. It’s not corporate. It’s about getting shit done, fast, and being prepared to take risks and back yourself. Near enough is good enough and being uncomfortable most of the time is important.
Unfortunately not everyone is suited to working in a start-up and that is why attitude and curiosity are some of the greatest traits to look out for. Will beats skill every time for me. I’d much prefer to hire someone that doesn’t have all the answers, but can demonstrate resourcefulness and an ability to take ownership and accountability.
Ultimately in building a team I look for people who have the ability to operate independently but also have the ability to work with other people and have fun. High performance is about commitment and accountability, and my role as a leader is to give people the confidence to execute and back themselves – waiting for someone to make a decision is a growth inhibitor. It’s key for me to let my team know I have their back, and it’s okay to take a calculated or educated risk.
What are some of the unique challenges you’ve faced starting a gifting fintech company such as YouPay in a crowded market with similar offerings?
I wouldn’t say we’re in a crowded market – yet. In fact, our biggest challenge has been educating the market on the real advantages of using YouPay as their gifting solution.
Connecting people at the checkout was the original vision for YouPay, and while this was initially constrained to e-commerce, we’re now delivering the same experience for physical retail stores as well.
With so much focus on privacy and security, plus the vast range of gift card scams that are happening, YouPay is helping people solve the many challenges of gifting such as distance and poor gifting experiences (not getting the gift you want, not knowing if you bought the right gift), and it’s also enabling gifting culture to go beyond special occasions. We are shifting the gifting approach to the recipient, and empowering them and the people around them to benefit from giving people what they really want. So the challenge really for us is creating awareness.
YouPay users are sticky. Once you’ve had the experience of having someone buy something for you that was on your wishlist, you won’t go back to hoping you might get the gift you want!
About Adrian Jenkinson
Adrian Jenkinson is the Chief Revenue Officer for YouPay. Following a successful corporate career, Adrian has devoted the last 12 years to partnering with start-up founders to help them execute their vision. With over 25 years of experience in business leadership, business operations, sales and marketing, covering a range of businesses from multinationals through to small enterprises, Adrian has a track record of helping businesses and teams drive triple-digit growth through structured and targeted marketing and data-driven business development practices. Companies Adrian has worked with include NAB, American Express, Bankers Trust, MYOB, Agility Consulting and more recently Wealth-X, SmartFee, Market Lend and Healthcare Logic.