Ray Riley

Chief Executive Officer, Progress Retail
Ray Riley is the Chief Executive Officer of Progress Retail, an operations and learning platform for retailers and brands. 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 Terry Hawkins & Ray Riley, and is principally headquartered in Chicago, Illinois, with an office in Sydney, Australia. To learn more, visit: <a href=""> </a>
  • Posted on: 06/06/2022

    Allbirds is no longer flying solo after deals with Dick’s and Nordstrom

    It's tough for single-category retailers to make it strictly with owned physical stores and online. Like all the "DTC darlings" Allbirds needs to get to profitability. Following in the footsteps of Casper opening up wholesale, expect others (Away as an example) to follow suit.
  • Posted on: 03/24/2022

    Has Warby Parker reinvented its business model?

    Warby has raised over $500 million in the past 12 years to reach $250 million in revenue, and a loss last quarter of $45 million. Its business model is under pressure to demonstrate profitability, and they clearly view stores as a vehicle to drive that initiative. Pricing and product (i.e. moving towards progressive lenses) is only one piece of that strategy as this cache of brands (e.g. Allbirds) are all having to settle into the reality of being a traditional retailer that has exhausted private capital.
  • Posted on: 10/05/2021

    Is consumer-direct less profitable for brands than selling wholesale?

    I didn't think "omnichannel" as a buzzword could be eclipsed in retail circles, but DTC has taken that prize. The decision for direct versus wholesale has many factors. Gross margins, variable fulfilment costs based on weight of products, and purchase frequency come to mind. In other words, if you're a DTC mattress company (lower purchase frequency), do you really want 100+ of your own shops in the U.S., or will having a more balanced wholesale presence in places like Costco or Bed Bath & Beyond where physical customer traffic aggregates make more sense? In this case, we're already seeing this one play out on both ends of the spectrum with Casper.
  • Posted on: 09/27/2021

    Will reducing seasonal hires pose a big risk for Target?

    Based on Target's 2020 Q4 metrics, they've likely right-sized their bet on where they will need support (in-store digital fulfillment), and can best leverage those capabilities with trained and seasoned existing staff.
  • Posted on: 08/19/2021

    Has Target ‘only begun to scratch the surface of what’s possible’ for its business?

    Target is Mall 3.0. With the stores-within-a-store from mammoths like Ulta and Apple to emerging growth stories like the ear-piercing hit Rowan (in ~200+ locations). It's *the place* to acquire curated brand and off-brand across such a swath of categories in a convenient and efficient way. How and where Target integrates these concepts shows a lot of runway for additional revenue opportunities.
  • Posted on: 08/17/2021

    Are over-attentive associates creeping shoppers out?

    The headline could read: "Stores that don't comprehensively invest in developing their teams risk creeping shoppers out." The skills of deep listening, tonality, accurately reading the customer's body language, and being aware of *our own* body language go a long way towards ensuring that the needs of the customer are met when they are in our store. Irrespective of store format or channel.
  • Posted on: 08/12/2021

    Does retail have a problem with how it recruits and hires workers?

    A compounding problem requires a compounding solution. Let's start with the three Ts: Tools, Talent, and Training.
    1. In terms of talent, are the multi-site leaders and store leaders developed to effectively induct and develop new hires that have met the criteria and standards of the brand?
    2. In terms of tools, does the organization provide its team and prospective team the tools and resources to onboard efficiently, remove friction from the onboarding cadences, and maximize that team member's "time to productivity"?
    3. In terms of training, does the organization provide that team member with another 50-page PDF or tattered employee handbook that hasn't been updated for the past 5+ years? Or do they provide dynamic and measurable, video-based induction content that can inspire, as well as set the standards of what teams must *know and do* on the shop floor?
  • Posted on: 08/04/2021

    Prime members will have to pay for grocery deliveries from Whole Foods

    I would expect this is Amazon's way of driving delivery business to their Fresh banner where more and more items are private label with higher margins. As a weekly Fresh customer in Chicago, I love the free delivery within two-hour windows. This delivery fee via Whole Foods allows Amazon to strengthen margins on fulfillment by creating more efficiency with delivery cadences from Whole Foods locations - where the volume of in-store fulfillment has marred their in-store experience (a frequent complaint from customers and analysts alike). It will be very telling should Amazon apply the same fee to their Fresh delivery business with the two-hour windows currently being free.
  • Posted on: 07/29/2021

    Store associates shouldn’t have to be the mask or vaccine police

    If each retailer was capable of having their own trained security on staff, then proof of vaccine to shop unmasked is reasonable. However that is not practical, thus the CDC needs to recommend a policy that isn't ambiguous, practical, and considers the realities of the often younger and vulnerable front-line workforce that aren't trained nor expected to be on-staff security.
  • Posted on: 05/20/2021

    Can Wayfair fend off the bigger guys?

    Right? I understand we're coming off a very challenging year - albeit not in the homewares category - so some spin is natural, but a highlight such as this is plainly yawn-inducing: "In the first quarter of 2021, 60.0% of total orders delivered were placed via a mobile device, compared to 54.8% in the first quarter of 2020."
  • Posted on: 05/20/2021

    Can Wayfair fend off the bigger guys?

    Consumer demand is one (important) element of a viable business. While gross margin improved from 2020 to Q1 2021, there are a number of vanity metrics in the Q1 report that makes one wonder what's not being shared. Revenue had to jump $1.1 billion to escape the $285 million loss on the last quarter. If I'm at Wayfair I'm praying consumer demand doesn't wane as the pandemic fades.
  • Posted on: 05/13/2021

    Simon says J.C. Penney is ready to become a 21st century retailer

    Outside of cutting costs and emerging from bankruptcy less debt-laden, it remains unclear what will generate growth. At nearly 22 years into the 21st century, even with "new brands," there needs to be a radically different value proposition for why new droves of customers would visit a J.C. Penney physically or digitally.
  • Posted on: 11/24/2020

    To furlough or not to furlough?

    There were dozens and dozens of instances where retailers immediately and inhumanely laid off teams as of March 15-16; the onset of the shutdowns. Regardless of the balance sheet realities for any of these companies, the ability to deal with the situation in an empathic manner was lost, in addition to team member good will.
  • Posted on: 11/13/2020

    Should C-suite execs keep their opinions to themselves on store visits?

    On one hand it is critical for retail organizations to develop a resilient, feedback-oriented culture at all levels and roles within the business. On the other hand, if the C-suite is finding themselves critiquing in-store behavior, operations, or execution, they should look internally first, and then at the divisional retail heads, multi-site or district teams that they've employed.
  • Posted on: 10/07/2020

    Apple removes other brand audio products from its store shelves

    Apple has had third-party products in its store in nearly all categories outside of desktop, phone, and laptop for years, and clearly they identified in the audio category what was working and what wasn't - mind you at full MSRP. They now have an opportunity to introduce product lines reflective of that data that are likely better in quality and higher in margin within their coveted four-wall physical environments.

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