Ray Riley

Chief Executive Officer, Progress Retail
Ray Riley is the Chief Executive Officer of Progress Retail, a retail e-learning platform that layers retail management, productivity, and communication tools on the foundation of personalized sales, product knowledge, organizational, and management training content.

Born in Michigan to college professors, Ray rebelled in early 2009, and left college after two semesters to expand a wholesale company he started earlier that year dealing in cell phones, parts, and cellular accessories. Shortly thereafter, he scaled this business into operating wireless retail stores, which continued the course for an entire career based in several functions within the retail industry.

His passion lies in the development of front-line retail teams and the convergence of technology within a brick-and-mortar environment. Progress Retail is led by Ray Riley, Terry Hawkins, and Kash Movania, and is principally headquartered in Chicago, Illinois, with an office in Sydney, Australia.

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  • Posted on: 06/19/2018

    Best Buy makes health and wellness tech a strategic priority

    Very smart. A large aging segment of the population in a country whose medical system is not without its faults. There's going to need to be a massive training initiative that will cost money, but frankly there isn't a retailer outside of Apple with their WatchOS heart and health apps that can segue into this space as easily.
  • Posted on: 06/19/2018

    Will an online dating site formula work for pop-ups?

    Do I agree that pop-up shops are what will entice shoppers to get off Amazon as the co-founder suggests? No. The nature of a retail outlet's lease isn't going to do that. There are no shortage of "marketplaces" that fancy themselves as Airbnb for retail space particularly with the retraction in physical retail CRE. They solve a real problem, and at face value it's great for the industry. Trust is a major component in retailing, and depending on what the pop-up shop sells, the "experience" could be negatively impacted by a "here today -- gone tomorrow" reality. As an example, I'm not sure if I'd want to invest in a pack of yoga classes with a pop-up tenant. Or what if I need post-sale service related to a product I've purchased? Landlords (GGP, Simon, Macerich, etc.) will look to increasingly dominate this space, so that they can control more of the standard.
  • Posted on: 06/14/2018

    Reasons you’re afraid of retail sales training and what to do about It

    I believe the issues tend to lie within the structure of the retail organizations themselves. Depending on the background of the HR leader, they may be more compliance and risk focused, whereas learning and development in the sales training context is not a priority. Therefore a L&D manager role is absent and, if present, they will follow the bouncing ball set by the HR leader. If the head of stores or head of retail has a merchandising or marketing background, they will tend to undervalue the importance of implementing a process for sales and service. Or they will shy away from it, because it isn't instinctually in their DNA. True retail sales leaders in the executive ranks with relevant front-line experience are a rare breed. It certainly has absolutely nothing to do with those on the front-line. There are no bad students; just bad teachers. The talent drain in retail has negatively impacted the quality of internal promotions based on merit and development. For example, there are regional managers in global retail businesses running $25 million units that struggle to analyze a P&L statement. This is an employer issue that needs correcting. Managing effective learning at scale is two-fold. First, there needs to be an effective in-person facilitation element that gets buy-in from a store and district/regional management level. This hopefully conveys a very clear process and framework which customers will experience, because sales professionals will execute. Second, there needs to be a scalable training curriculum that enables information and communication to be distributed to every member of the retail team regardless of location or position. This requires a learning management or sales enablement system, something that our research shows that half of retailers don't possess. You can't segregate information and education from members of your front-line team, especially when each member will be serving customers, and foot traffic is in decline.
  • Posted on: 06/12/2018

    Should retailers incentivize store staff to accept digital transformation?

    I've been on the front line of leading and facilitating this kind of change, and one thing is for certain: incentivizing fails. The future role that manages retail learning and development needs a total overhaul just as the future front-line retail sales professionals and managers need more than a features, advantages and benefits card with a new range of merchandise. These front-line staff will be taking on more and more over the next five years. As alluded to in the article, that learning and development job role facilitates in-person and virtual training for any new transformative initiative that will integrate with brick-and-mortar. Every individual who interacts with a customer must be reached somehow. The learned and development individual must be capable of explaining WHY this initiative is headed into stores in a way that resonates. They must be clear about WHAT the impact will be for customers (most importantly) and how it makes the sales professionals' role easier -- with the potential for increased sales/commissions. Then it simply comes down to HOW execution happens, and this is where practice is required. Generally, piloting an initiative with a leading store(s) and manager(s) enables a champion to emerge that can internally spearhead this change at a peer level -- creating a much stronger bonding effect. This learning and development role requires a skilled person who has front-line retail experience and understands how to integrate transformation on the shop floor, and how its standards are managed by a store manager. Clearly desired outcomes or KPIs must be defined at the HOW stage, so that no one is left in the dark.
  • Posted on: 06/11/2018

    Brands win with TV 2.0 and the new direct mail

    A good strategy encompasses a tested balance of tactics which would include TV advertising. With localized TV advertising, retailers can pinpoint their audience by postal code and quantifiably measure success as opposed to using the broad brush approach of the past. Brands are absolutely mistaken to completely turn their backs on any channel, especially traditional formats, as our digital inboxes and smartphone screens are inundated with noise.
  • Posted on: 06/08/2018

    Retailers told to forget social media

    I believe that in many retail circles over the last few years "social media marketing" was considered the answer. Much like the reactionary, laser-focus on e-commerce, it was all tactics and no strategy. Tactically, social media is a critical part of a digital marketing strategy, but it certainly isn't where all resources should be deployed and its effect will vary by vertical. It's an important brick in the wall, along with other analog and digital forms that still reach customers.
  • Posted on: 06/07/2018

    Retailers get real with high-touch service

    Really enjoyed this read. The old tricks don't work anymore, and so many authentic brands are realizing what actual personalization means. It's not a social media campaign. There will always be a degree of humanity involved in personalization efforts, and retailers need to empower their front-line teams (that cost 10-20% of revenue) to behave and perform in ways that builds marketshare and advocacy. The scalable, "painting with a broad brush" approach to sales and service in physical retail hasn't worked for years, and has been exposed by simple, virtual zero-click ordering. Cutting through the noise is exactly what is required.
  • Posted on: 06/06/2018

    Macy’s taps staff for their influencer clout

    The retail sales professional and store associate are beginning to have a renaissance as retailers have begun to empower them more in order to reach customers, and create deeper engagement. The upside is sales professionals will have deeper engagement in their work as their employer is providing them with additional purpose, and assumingely some play as well. As mentioned heavily in the comments, authenticity will be essential: "You get paid to say that" could become a consumer reaction in some cases.
  • Posted on: 06/04/2018

    Can department stores be reinvented with a pop-up approach?

    In-store execution in traditional retail is hard enough, and while pop-up shops have been in vogue, the in-store outcomes vary wildly. Each department store would benefit from having a part of a floor sectioned off for exclusive merchandise only available at this location, creating the "treasure hunt" element that has been so successful in discount and off-price. Ultimately, the customer decides based on the range of product, and level of service within the environment.
  • Posted on: 06/01/2018

    Walmart’s newest service brings texting and personal shopping together

    Continuing to zig as Amazon zags with an emphasis on human connection and leverage. Competing with Amazon on price isn't sustainable, and Walmart recognizes this by the series of training, education, and now concierge-style initiatives being rolled out. Walmart is clearly going after a target demographic with Jetblack, and I'm sure they'll have loads of data scientists and analysts paying attention to each algorithmic recommendation for accuracy and customer satisfaction. They could just nail it before they scale it.
  • Posted on: 05/31/2018

    Walmart looks to win talent war with new education benefit

    As Scott Galloway says, "zig as Amazon zags." Amazon can't compete with having a skilled sales and service folks on a sales floor. This is an outstanding initiative to attract, develop, and retain team members. Walmart deserves a lot of credit for the emphasis on continuing education and investing in their front-line, especially with the recent Strivr Virtual Reality implementation.
  • Posted on: 05/29/2018

    Kohl’s emphasizes cash in merging of rewards program

    Brilliant move consolidating and simplifying this loyalty program, and a cash emphasis always wins. If customers can simply communicate the program to other customers -- that's how awareness and consideration is seeded. I'm very curious to see the next evolution of Kohl's loyalty program with what could be the next stage of their Amazon partnership, and Amazon's branded credit card.
  • Posted on: 05/24/2018

    Is excess space behind retail’s shrink and customer experience problems?

    The statistic I love to lead with was from L2, "Between 1970 and 2015 malls grew at twice the rate of the human population." This is still an issue being dealt with by developers and PE groups, but that's on the supply side. The composition of the individual stores' bloated floor plans and sprawling inventories is a remnant of that era that is much trickier to fix. As populations (Gen Y/Z) are shifting more towards urban cities where smaller store footprints are the norm, the suburban outlets that already struggle to find talent for the shop floor experience a compounding effect: no staff, way fewer customers, but still the same costs. Unless the retailer can give back part of their oversized footprint to the shopping center (which is happening in some cases), they need to focus on repurposing that space for non-sales to generate awareness and interest through events or product demonstrations -- just as examples. They then can create a sustainable area for sales management and LP risk, while attempting to attract new customers.
  • Posted on: 05/23/2018

    Lessons in goodwill and the power of feelings

    Spot on Chris. There are some retail establishments you do feel more positive walking into -- whether that's Apple, Whole Foods (well ... we'll see how long that lasts), Suitsupply, etc. I think it's quite clear that this is a top-down approach driven and demonstrated daily by leadership at every level and function.
  • Posted on: 05/23/2018

    Best Buy’s Geek Squad is now available by subscription

    This is a great move, and I agree with much of what has already been said. There is a large segment of America retiring and becoming less mobile, but will still require assistance as technology infiltrates more of their homes and lives. Could be the go-to Christmas gift from sons and daughters to their parents. This is a great move by Best Buy, and frankly no other retailer (aside from Apple) is positioned at scale to compete in this space.

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