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: 12/14/2018

    Does Starbucks have a big delivery opportunity?

    Is it the normal $2.50 delivery fee? I can tell you there are plenty of folks in my generation (in cities) that order Uber Eats or Grubhub from food outlets that are a stone’s throw from their condo or apartment. I’m curious to know the delivery fee (Uber Eats standard $2.50-$3.50?), but I don’t see coffee being any different pending the product arriving in the optimum condition.
  • Posted on: 12/13/2018

    Retailing success doesn’t depend on silver bullets

  • Posted on: 12/13/2018

    Retailing success doesn’t depend on silver bullets

    Yes Rich! Turn compliance and tasks into energy creating activities for the in-store teams to love, and in-turn transfer that energy to customers. Sounds like a great plan.
  • Posted on: 12/13/2018

    Retailing success doesn’t depend on silver bullets

    Agreed Ralph. Products are always changing, and the consumer has instant access to product details at all times. I think the emphasis is (and has always been) solving problems for customers through expert human connection, in addition to basic sales and service skills. I view products and transactions as the outcomes of that. We've all seen the car salesman who can rattle off the horsepower and 0-60 metrics, but not actually understand the buyer in the slightest.
  • Posted on: 12/13/2018

    Retailing success doesn’t depend on silver bullets

    So true Georganne!
  • Posted on: 12/13/2018

    Retailing success doesn’t depend on silver bullets

    Congrats on the book Peter — mine just arrived earlier in the week!
  • Posted on: 12/13/2018

    Retailing success doesn’t depend on silver bullets

    Love the QB reference. I totally agree.
  • Posted on: 12/13/2018

    Retailing success doesn’t depend on silver bullets

    Thanks Bob.
  • Posted on: 12/12/2018

    Where will Amazon go with its cashier-free concept?

    There is huge potential in office buildings, airports, and international locations. I'm more interested in how Amazon goes about it. Do they acquire a Rite-Aid like player? Launch a franchise model in order to initially attain scale -- particularly in more rural and suburban markets?
  • Posted on: 12/11/2018

    Will ‘Practice’ make for perfectly loyal customers at Lululemon?

    At $128 it's an offer filled with value that Lululemon's customers are already all about. It's more than just product (personal development courses, events, and yoga sessions) which on its own costs way more than $128 a year.
  • Posted on: 12/06/2018

    Walmart: Floor cleaning robots will give associates more time to serve customers

    Earlier this week we were concerned associates at Walmart would be preoccupied fulfilling out of stock orders on mobile apps. And just like that -- Walmart responds with the answer. I think this is more smoke and mirrors from Walmart, and I’m not buying that having an autonomous floor scrubber will therefore improve in-store customer service, or effectively free up associates to serve shoppers.
  • Posted on: 12/04/2018

    Walmart gives associates a tool to deal with out-of-stocks

    A tool for this and a tool for that. Technology is intended to amplify human capacity, so in the narrow function of enabling out-of-stock merchandise, this is great. However, retailers of all shapes and sizes need to be thoughtful about the overall utility of technology they are providing store associates. Too many tools create little engagement, and a ton of cash laid out for little ROI. I don't see this requiring Walmart to increase staff; they can easily get a kiosk that can automate this entire process after testing its success with live team members.
  • Posted on: 12/03/2018

    Can Gap cut its way to profitability?

    Nope. They need to rationalize the store portfolio, get better clothes to sell (closer to Intermix), and invest in their people to differentiate Gap as a retail employer with growth opportunities.
  • Posted on: 11/30/2018

    Is J.Crew’s new Amazon relationship already over?

    +9 percent on a previous -8 percent is no cause for celebration. So after a flat trade period, J.Crew is making some (hopefully) positive changes in the merchandise area. I can't imagine there's much more patience left in the tank as the capital expenditures related to the Nervereven and Mercantile projects would not have been insignificant.
  • Posted on: 11/29/2018

    Store employees of the future will be affiliates, not associates

    There's a split on this trend. In multi-brand high-touch retail, where there is a sense of artistry such as high-fashion, hair/beauty, and cosmetics -- it is a critical distinction that people not only visit stores for those products, they buy from people they generally like. The retailer is in a balancing act between supporting the team member who is driving revenue and maintaining control over their customer.

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