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. To learn more, visit:
  • Posted on: 11/21/2019

    Is Target killing department stores and specialty clothing chains?

    This isn't generational. Target has conveniently located stores with a relevant urban presence, and (it goes without saying) has the product mix that creates time efficiencies for shoppers.
  • Posted on: 11/06/2019

    Food halls drive mall traffic, not clothing sales

    This is where retail theory has gone wrong. In theory, enabling opportunities in shopping centers for human beings to congregate (food halls and co-working) is a no-brainer, until we profile the young freelance graphic designer who is utilizing the co-working space, and not purchasing new clothing. If not for sustainability reasons alone, landlords have to attract (fashion) e-commerce marketplaces to open up shop, get closer to customers, reduce waste, and be a return/exchange fulfillment point.
  • Posted on: 10/25/2019

    What makes a great assistant store manager?

    It's a great list, Bob. Great managers are developed and not born, so where are the comprehensive store management training and development programs? Just because the average retailer may not be opening 10-20 stores a year, doesn't mean development of store (current and future) leaders stops - yet so it seems. Increased responsibilities should be met with increased developmental opportunities!
  • Posted on: 10/02/2019

    Foot Locker invests in streetwear e-commerce platform

    As the article states, this is a lot more than just e-commerce. The cultural aspects of streetwear enables Foot Locker to get closer to a younger customer whose eyeballs will be fixated on the episodes, drawings, and chat functions within the platform. It's a massive data lake that will be warehoused and filtered into Foot Locker's physical locations.
  • Posted on: 09/26/2019

    Amazon tests program to take better care of employees’ health

    Amazon Care is the pilot program for the broader announcement from Bezos, Jamie Dimon, and Warren Buffett made in January of 2018. This is a very large group where the healthcare model can be refined for broader application. We already receive our batteries, bananas, and video content from Amazon -- next up: healthcare.
  • Posted on: 09/24/2019

    Do retailers need better business intelligence tools or a better analytic strategy?

    It comes down to the quality of data on the input side, and the retail point-of-sale in many of these cases is to blame. It’s a crowded ecosystem of middleware and aggregation tools, but until the source data gets it right the fanciest tools or strategies are always an uphill battle.
  • Posted on: 09/16/2019

    How profitable is online selling?

    Paid social and search are only getting more expensive in practically all categories. For consumer brands, this is definitely a hurdle with a typically lower average transaction value. This is one of the steepest hurdles that has grown in the past five years in particular as the eyeball aggregating platforms have grown to mega-scale. Another money pit being the freight/fulfillment space, which is increasingly becoming more interesting (Shopify's acquisition of 6 Rivers), with innovation hopefully paving the way for significantly reduced costs to merchants.
  • Posted on: 09/04/2019

    Will miniature Meijers be a big hit?

    As a former Grand Rapids resident, it was an easy 15-20 minute drive out of the city to get to meaningful shopping. This was also prior to the delivery and fulfillment age we live in now. Miniature Meijers and Targets fulfill a huge customer need in cities where population growth is steadily increasing.
  • Posted on: 08/09/2019

    Can Victoria’s Secret recover from its founder’s past relationship with Jeffrey Epstein?

    I don’t find Victoria’s Secret’s issues to be related whatsoever to Wexner’s past relationship with anyone. However, the broader (and awful) claims made in the letter add insult to injury for a brand attempting to regain relevance and social equity.
  • Posted on: 08/06/2019

    What are the signs of a dying retail business?

    Adding to the great list above would be the deterioration of stores. Are there lights out in the window? The carpet or floor trashed? Scuffs and gashes at the corners of the cash-wrap? The clock is ticking.
  • Posted on: 08/01/2019

    Should Simon Property Group bail out (invest in) more retail tenants?

    Generally speaking no. However, Simon and all mall operators need to be thinking about a 21st century partnership model that involves providing those retailers with resources at the coalface of their field operations. Whether that is providing learning and development opportunities for store teams, or meaningful ways to drive foot traffic (not valet parking) - there's more to the relationship than merely square footage.
  • Posted on: 07/23/2019

    How long is the customer journey?

    As retailers shift to operating as a platform (Lululemon being a recent practical example), the journey is not and should not be thought of as linear.
  • Posted on: 07/19/2019

    What does it take to develop top retail store managers?

    From my personal experiences of being a store manager and leading store managers, there is a lightbulb moment that occurs when one realizes their success is truly delivered through the success of their sales professionals via optimized interactions with each and every customer. For anyone that hasn't been in the role that may sound vague or ambiguous, but most managers were promoted due to their individual performance, while (as Bob mentions) in #1-5 management and leadership are a different game.
  • Posted on: 07/02/2019

    Are offline experiences becoming more important to online performance?

    More important than five years ago? Probably not. Distribution is the name of today’s game, and if you don’t have a physical presence to work with the customer- you’re extremely disadvantaged. The offline transaction is 8x larger, but is heavily influenced by online channels and vice versa. This requires a solid generalist retail operator who can get the first fifteen stores up and running in a disciplined fashion with respect to VM, HR, and training.
  • Posted on: 07/01/2019

    Can mobile sensing tools boost worker productivity?

    As the saying goes, “every technology is utilized before it is fully understood.” - and that seems to be much the case with this kind of tech. If the data was solely provided to employees with comparisons and insights, there could be benefits to improving health and therefore productivity. However employers will want a greater benefit, and even with anonymized data there’s privacy risks particularly in smaller teams.

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