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: 03/23/2020

    Costco is refusing returns on hoarded items

    It's rare I don't side with the customer, but there's nothing normal about what is going on at the moment. Costco or any retailer shouldn't have to pay for these consumers behaving foolishly.
  • Posted on: 03/09/2020

    Burlington Stores walks away from e-commerce

    The move itself makes perfect sense, but how many other other components of a retailer's online presence will Burlington forgo? As I browse the website for a treasure hunt item, can I verify that it is actually in stock and in my size prior to visiting the store? No. Can I purchase the product online with only the option of picking it up in-store? No. Will new arrivals or close-out deals be advertised or displayed on their Instagram page -- with the opportunity to then convert as above? Killing off e-commerce due to the unit economics of their merchandise mix is one thing, but where does that sit within their greater strategy to delight existing customers and attract new ones?
  • Posted on: 02/19/2020

    Will store associates become the ultimate personalization tool at retail?

    Oftentimes training is a “tick the box” item. An “Oh we did that.” kind of thing. In physical retail today where the product has been reduced down to a minimum standard commodity, “training” or better yet “learning and education” needs to become a lot more comprehensive to reflect the modern retail ecosystem we all live and consume within. For example: a basic “steps to the sale” just isn’t enough. Outside of education this includes transparently sharing data from e-commerce and marketing so that their role and their store’s role is reframed in a way that they recognize the significant impact they have. This then begins to address the talent attraction piece which is a story for another day!
  • Posted on: 02/14/2020

    Is it time for retailers to move beyond fulfillment and on to experience?

    In specialty retail it is still an uphill climb. Many 100+ store chains are still dealing with legacy POS as a major hurdle - therefore limiting their ability to get a solid read on customer and transactional data. With respect to the other question, I would love to replace omnichannel with just: retail.
  • Posted on: 01/29/2020

    The measured store, version 2.0

    As a baseline, in-store traffic has been beneficial for over twenty years for optimizing labor spend. More recent technologies have added additional layers to this data, but the privacy and regulatory concerns are still an unknown entity as customer in-store behavior is married with marketing and transactional data. So many retailers at various segments have no form of in-store traffic tech, which no doubt means the category will continue to grow. The question becomes for the modern store: are your front-line team members skilled to relate and understand to customers at various stages of their journey to maximize opportunity?
  • Posted on: 01/17/2020

    NRF 2020 Review: Human vs. Machine

    The spectrum involving robots and humans is paralleled by the spectrum of low-touch to high-tough retail where the in-store team member is a critical component. Contextually, robots and other incredible technologies did not appear to be a primary concern for retailers (that we met with) of higher-touch categories - particularly when in relation to in-store operations. No doubt in lower-touch retail environments robots, machines, and other artificial human intelligence will continue to grow. “Amazon Go”- like stores will continue to open and be successful, and we will no doubt see some form of virtual help within these retail environments.
  • Posted on: 12/27/2019

    Holiday bonuses are tricky (or nonexistent)

    The overall nature of compensation is changing with the makeup of the retail workforce, but simply put: sales teams in specialty retail should be incentivized to sell. There’s a greater opportunity that will lead to more positive behaviors on the store floor - when aligned with the right package of training and development, which is for managers and multi-site managers to be given bonuses based on a composite read of performance of their store or group outside of just revenue or profit targets. For example: bonus thresholds that include the store (or group) running at less than “x number of weeks” understaffed, or achieving a percentage of “ready” assistant managers, or aligned with a positive CX metric. With many digital factors influencing store performance, it’s time to review the roles and the associated bonus compensation to attract and retain the best players.
  • Posted on: 12/16/2019

    Will Hudson be more than just a newsstand with a new look?

    An old model with low ATVs in a high potential retail environment needs more than a new look. I stopped in a Hudson two weeks ago and couldn’t even tap to pay with NFC/Apple Wallet. Rifling through my bag post security to grab a card for a $4 bottle of water isn’t ideal.
  • 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.

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