Ray Riley Of Progress Retail On 5 Things You Need To Be A Highly Effective C-Level Leader Of A Retail Tech Company

An Interview With Kieran Powell

Spend time talking to end-users. At Progress Retail, our end users are largely front-line associates, store managers and multi-site managers. They are at the coalface of customer experience and are directly involved in all aspects of store operations. This is a breeding ground for uncovering opportunities and prescribing solutions.

The retail industry is undergoing a seismic shift, largely driven by technology. From e-commerce to AI-driven customer experiences, technology is redefining how consumers interact with retail brands. This rapid transformation presents unique challenges and opportunities for C-level leaders in the retail tech space. Effective leadership is more critical than ever to navigate these changes, drive innovation, and maintain a competitive edge. As part of this series, we had the pleasure of interviewing Ray Riley, CEO of Progress Retail.

Ray is the CEO of Progress Retail, a retail operations platform making multi-store operations easier, retail employees more productive, and driving store transaction values higher. Ray is a career-long retail operator with various experience and roles in multiple retail categories. Based in Chicago, Ray is passionate about physical retail, and how technology is designed and implemented with respect to the nuance of stores and the evolving role of store teams.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

From age 17 onward I have been working in or working with stores. After leaving corporate retail in 2016, I was introduced to a then business partner who came from the retail education space. Initially, we wanted to provide retailers with a learning platform bundled with dynamic training content — solving two problems at once for retailers: 1) having a scalable means of delivering and tracking training, and 2) providing meaningful content beyond what is so often a stale, analog, and ineffective experience that doesn’t drive business outcomes. From there, the plan was to expand the product into more broadly retail operations, and multi-site management capabilities.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Anyone that has taken this kind of leap has their share of mistakes. Especially in the early days (although it doesn’t ever stop- it just becomes different) there is so much to do. Building out collateral, updating a website, getting testimonials, feature development, customer success, generating demand/revenue, etc. Managing one’s time is paramount, and being conscious of what commitments have been made, in addition to who you are involved with that can either support or detract from your capacity can be make or break.

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

Our mission is to enable each retail employee to connect more effectively with themselves, their colleagues, and customers. In the realm of managing retail performance individually and as a group, we believe we have some interesting applications “in-store” for 2024.

Thank you for that. Let’s now shift to the central focus of our discussion. The retail industry has seen a significant shift towards digital and e-commerce solutions. How have you adapted your business strategy to this digital transformation, and what challenges did you face in this transition?

Like many companies in the space we operate in, when we first got started our product was a bit early, and retailers largely at that time (2016–2017) had other burning platform priorities involving e-commerce, point-of-sale transformations, and the like. So, from a challenge perspective, it’s about aligning on priorities and timeline, and discovering retailers that are aware or can become aware they have problems that need solving. In saying that, our strategy largely remained the same as we continue to work closely with retailers to transform current ways of working within store operations, communications, and training.

Retail technology is heavily focused on enhancing customer experience. Can you share a particular innovation your company has implemented to improve customer engagement and satisfaction? How did this innovation impact your business?

There has been a lot of discussion about the role of the in-store employee, and how that role will transform over time. And there are multiple variations of the quote: “A great employee experience creates a great customer experience.” At the end of the day, wages are a major expense for any retailer, and there are significant hidden costs associated with the mismanagement of retail talent such as: employee turnover costs, recruitment costs, lost productivity, potential overtime expenses due to understaffing etc. And anyone that shops in-store sees this play out firsthand. We have case studies that include decreasing onboarding time upwards of 50%; in other words that means that a new hire whose company supports them with Progress Retail is productive 2x faster. From a financial perspective, that is driving a strong return on that wage expense, and there is further data that these employees stay in their roles longer- therefore decreasing employee turnover. I could certainly go on in terms of increases in average transaction values, time savings, less emails, etc. which all enable employees to run better stores, and maximize interactions with customers.

Leading a retail tech company often means keeping up with rapid technological changes and market trends. How do you stay ahead of these trends, and what practices do you follow to ensure your team remains agile and innovative?

There is always a shiny thing in technology. Roughly, two years ago when we were in a zero-interest rate environment, all you heard about in retail tech was the metaverse. Whether those use-cases fully develop and see meaningful customer adoption remains to be seen, but I think the most important thing is to stay close to customers, intuit their needs and current challenges, and present relevant solutions that drive a tangible benefit(s).

In an industry increasingly dominated by technology, how do you balance the use of tech solutions with the need for a human touch in customer service and team management?

Not dissimilar to other tech verticals, in retail tech you often have the retailer as a client and their workforce as your end-users. Our implementation and onboarding process, in addition to our customer success model includes touchpoints with those end-users periodically throughout the relationship. As a former store employee myself, I’m hyper aware of the disconnect that can occur between store level and executive leadership. So in more ways than one, that is a gap we are focused on minimizing.

Based on your experience and success, what are the “5 Things You Need To Be A Highly Effective C-Level Leader Of A Retail Tech Company?” How have these 5 things impacted your work or your career?

1 . Deeply understand customers current ways of working and aspirations. Executives and middle management in the retail industry have vastly different backgrounds and technical experience. For example, two 100-store chains can be polar opposites in terms of their internal technical capability. Based on the personas you engage with client-side, it’s really important to understand how those individuals are composed within their organization, and engage each of them to understand their workflows and how your solution can add additional value.

2 . Spend time talking to end-users. At Progress Retail, our end users are largely front-line associates, store managers and multi-site managers. They are at the coalface of customer experience and are directly involved in all aspects of store operations. This is a breeding ground for uncovering opportunities and prescribing solutions.

3 . Question everything. This goes both ways: internally within your company that is providing solutions, and client-side. There are symptoms and there are core issues, and engaging in open questions such as “How does this help you?” “How much time are you spending on this?” Why would A work, but B would not?” “What would be the ideal scenario for how to handle this?” can get you closer to understanding and creating solutions. When it comes to internally, it must become cultural. What is most important is that your organization arrives at the right conclusion. A company exists to create value and solve problems for customers, and that has to be an egoless experience. Questioning current practices, processes, allowing for reflection, and paying close attention to prospect and customer signals can ensure that you are one step ahead.

4 . Onboarding & Implementation is key. In retail tech it is rarely “the what”, and it is often “the how”. How your solution is implemented into the client’s organization, and embedded within their day-to-day workflows is critical. Many retailers are under-resourced with no shortage of priorities, and there is only one shot at a first impression. Our level of white-glove service has been important for successful implementations.

5 . Optimize sales process regularly to minimize sales cycles. Depending on the stage of your company, as a leader you may still be somewhat or heavily involved in acquiring customers and generating revenue. When possible, it can be incredibly valuable to have non-sales roles attend discovery calls and demos. They may have feedback or insights that can inform adjustments that can be made, while also exposing them to a core function of the organization. Revenue is oxygen, and without it you die. Sales cycles in retail — especially at the enterprise grade- can also be lengthy, which demands constant attempts at optimization.

Looking ahead, what do you believe are the key trends that will shape the future of the retail tech industry? How are you preparing your company to adapt to these trends, and what role do you see your leadership playing in this adaptation?

An obvious answer is artificial intelligence, but I would also forecast quite a bit of consolidation among vendors. For many retailers their tech stack has exploded, and constantly retailers are looking to reduce the number of technologies and make things easier. It’s a natural evolution.

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? You never know what your idea can trigger. :-)

Where to begin. I suppose based on some recent experiences with family and friends, I really hope our country figures out healthcare. A healthier society is a more productive society.

How can our readers further follow your work online?

Feel free to follow me on Twitter or connect with me on LinkedIn. Follow Progress Retail on LinkedIn, Twitter, Instagram, and Facebook.

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

About The Interviewer: Kieran is the EVP of Channel V Media, a Public Relations agency based in New York City with a global network of agency partners in over 30 countries. Kieran has advised over 150 companies in the technology, B2B, retail and financial sectors. Previously Kieran worked at Merrill Lynch, PwC, and Ernst & Young. Get in touch with Kieran to discuss how marketing and public relations can help achieve your company’s business goals.