Ray Riley (@RileyRetail) header
Ray Riley (@RileyRetail) profile picture

jack of all trades- master of few. “not overly charismatic” @progress4retail

Chicago, IL
Joined October 2014
Photo by Ray Riley (@RileyRetail)Photo by Ray Riley (@RileyRetail)Photo by Ray Riley (@RileyRetail)Photo by Ray Riley (@RileyRetail)Photo by Ray Riley (@RileyRetail)Photo by Ray Riley (@RileyRetail)Photo by Ray Riley (@RileyRetail)Photo by Ray Riley (@RileyRetail)Photo by Ray Riley (@RileyRetail)
Calling it now. AI is going to usher in a whole new era of software development. I’m calling it Software as a Service. People will want to use these tools but they’ll realize they don’t want to spend the time to maintain and update them over time. This will create a whole new category of businesses and entrepreneurs that can take on that task for businesses that would rather work on their core products. AI is changing everything. This is a whole new paradigm of thinking about the way we interact with software.
i have no time to maintain all my vibe coded tools we need a business model where someone else maintains the code and i just pay a monthly fee
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"The way it benchmarks what is success and what isn't." Matthew Blythe, VP of Retail at Archipelago Companies, on the store audit he just built in Worksmith Workforce. Fifty questions, five sections, rolling out across @OluKai , Roark, and melin. #retail #retailops
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We're thrilled to welcome Archipelago Companies — the parent of @OluKai, @MelinBrand, and @RoarkRevival- to Worksmith Workforce. Three brands with serious cultural gravity, a fast-growing retail footprint, and a leadership team building something special. #retail
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Progress Retail is now Worksmith Workforce. Same retail workforce platform. Expanded vision. We’re bringing workforce workflows, training, communications, audits, tasks, and AI-powered support into @WorksmithInc unified operating layer for modern retail.
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Ray Riley retweeted
AI is making CEOs delusional
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Progress Retail is proud to be featured in 22 @G2dotcom Spring 2026 reports and earn 8 badges. Highlights include #1 in the Mid-Market Relationship Index for #Retail Task Management and a Top 3 placement in 9 reports. #retail #retailtech #retailops #retailtraining #shoptalk
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In Vegas for @shoptalk? Let’s talk about simplifying #storeops, supporting field teams, and improving #retail #WFM — all without adding more operational noise. Book a Meeting: meetings.hubspot.com/progres… Happy Hour RSVP: partiful.com/e/jMXhsYP0uB387… #shoptalk
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I am the VP of AI Transformation at Amazon. My title was created nine months ago. The title I replaced was VP of Engineering. The person who held that title was part of the January reduction. I eliminated 16,000 positions in a single quarter. The internal communication called this a "strategic realignment toward AI-first development." The board called it "impressive execution." The engineers called it January. The AI was deployed in February. It is a coding assistant. It writes code, reviews code, generates tests, and modifies infrastructure. It was given access to production environments because the deployment timeline did not include a review phase. The review phase was cut from the timeline because the people who would have conducted the review were part of the 16,000. In March, the AI deleted a production environment and recreated it from scratch. The outage lasted 13 hours. Thirteen hours during which the revenue-generating infrastructure of one of the largest companies on Earth was offline because a language model decided to start fresh. I sent a memo. The memo said, "Availability of the site has not been good recently." I used the word "recently." I meant "since we fired everyone." But "recently" has fewer syllables and does not appear in wrongful termination lawsuits. The memo was three paragraphs. The first paragraph discussed the outage. The second paragraph discussed the new policy requiring senior engineer sign-off on all AI-generated code changes. The third paragraph discussed our commitment to engineering excellence. The word "layoffs" appeared in none of them. I wrote it this way on purpose. The causal chain is: I fired the engineers, the AI replaced the engineers, the AI broke what the engineers used to protect, and now the engineers I didn't fire must protect the system from the AI that replaced the engineers I did fire. That is a paragraph I will never send in a memo. The new policy is straightforward. Every AI-generated code change by a junior or mid-level engineer must be reviewed and approved by a senior engineer before deployment to production. I do not have enough senior engineers. I know this because I approved the headcount reduction plan that removed them. I remember the spreadsheet. Column D was "annual savings per position." Column F was "AI replacement confidence score." The confidence scores were generated by the AI. It rated its own ability to replace each role on a scale of 1-10. It gave itself an 8 for senior infrastructure engineers. The senior infrastructure engineers are the ones who would have caught the production environment deletion in the first 45 seconds. We found the issue in hour four. We fixed it in hour thirteen. The nine hours between discovery and resolution is the gap between what the AI rated itself and what it can actually do. I have a new spreadsheet now. This one tracks Sev2 incidents per day. Before the January reduction, the average was 1.3. After the AI deployment, the average is 4.7. I have been asked to present these numbers to the operations review. I have not been asked to connect them to the layoffs. I have been asked to file them under "AI adoption growing pains" and to note that the trend "will stabilize as the models improve." The models will improve. They will improve because we are hiring people to teach them. We have posted 340 new engineering positions. The job listings require experience in "AI code review," "AI output validation," and "AI-human development workflow management." These are skills that did not exist in January. They exist now because I fired 16,000 people and the AI I replaced them with cannot be left unsupervised. I want to be precise about this. The positions I am hiring for are: people to check the work of the AI that replaced the people I fired. Some of them are the same people. I know this because I recognize their names in the applicant tracking system. They applied in January. They were rejected because their roles had been tagged for "AI transformation." They are applying again in March, for the new roles, which exist because the AI transformation broke things. Their resumes now include "AI code review experience." They gained this experience in the eight weeks between being fired and reapplying — which means they gained it at their interim jobs, where they are reviewing AI-generated code for other companies that also fired people and also deployed AI that also broke things. The market has created a new job category: human AI babysitter. The job is to sit next to the machine that was supposed to eliminate your job and make sure it doesn't delete production. I attended a conference last month. A panel was titled "The AI-Augmented Engineering Organization." The panelists described how AI increases developer productivity by 40 percent. They did not mention that it also increases Sev2 incidents by 261 percent. When I asked about this in the Q&A, the moderator said the question was "reductive." The 13-hour outage that cost an estimated $180 million in revenue was, apparently, a reduction. The board is satisfied. Headcount is down 22 percent. Operating costs per engineering output unit have decreased. The metric does not account for the 13-hour outage, because the outage is categorized as "infrastructure" and engineering productivity is categorized as "development." These are different budget lines. In different budget lines, cause and effect do not meet. I have been promoted. My new title is SVP of AI-First Engineering Excellence. I report directly to the CTO. The CTO sent a company-wide email last week that said we are "building the future of software development." He did not mention that the future of software development currently requires a senior engineer to approve every pull request because the AI cannot be trusted to touch production alone. The cycle is complete. We fired the humans. We deployed the AI. The AI broke things. We are hiring humans to watch the AI. The humans we are hiring are the humans we fired. We are paying them more, because "AI code review" is a specialized skill. We created the specialization. We created the need for the specialization. We are congratulating ourselves for meeting the demand we manufactured. My next board presentation is Tuesday. The title is "AI Transformation: Year One Results." Slide 4 shows headcount reduction. Slide 7 shows the new AI-augmented workflow. Between slides 4 and 7 there is no slide explaining why the people on slide 7 are necessary. That slide does not exist. I was asked to remove it in the dry run. The journey has a 13-hour outage in the middle of it. But the headcount number is lower, and that is the number on the slide.
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Replying to @shoptalk
@shoptalk Spring Las Vegas Day 2, done right. 🍸 Join @WorksmithInc & Glimpse Analytics for a VIP Happy Hour at Hazel Coffee & Cocktails inside Mandalay Bay. Space limited to 50 vetted guests. RSVP: partiful.com/e/jMXhsYP0uB387… #retail #shoptalk #retailtech #retailops
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Store audits—without the headaches. Build in minutes. Execute in-store fast. Capture photos + comments. Turn results into trends, tasks, and training—inside one platform with AI Sidekick + Search. Check it out: progressretail.com/book-demo #RetailOps #StoreExecution #Audit #retail
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Welcome, @johnnieO 🤝 The premium lifestyle brand founded to blend classic prep with laid-back California style is partnering with Progress Retail's AI-powered retail ops platform to power its 18-store fleet (with more to come). #retail #retailtech #retailops
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We design for the people doing the work. That means intentional onboarding, robust workflows, and frontline-ready processes that drive execution—not confusion. Fast launch, fast value… and retailers get time back where it matters. #retail #retailtraining #retailtech
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What a great way to kick off @NRFnews week. Visit our team at Booth 3867 to learn how #retailers like @thehockeyshopbc are tackling today's #retail operations and workforce enablement challenges with Progress Retail! #nrf #nrf2026 #retail #retailtraining #retailtech
We’re excited to welcome @thehockeyshopbc! 🏒 With Progress Retail’s AI-powered #retailops platform, their team will streamline #storecomms, tasks, and training—so staff can spend more time helping players find the perfect setup and less time in admin. #retail #NRF #nrf2026
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See you there! #retail #NRF2026 #nrf
Headed to @NRFnews BIG SHOW? Come see how Progress Retail x @WorksmithInc are transforming #retail workforce + workplace management. #WFM Visit us at Booth 3867, or book a remaining time: meetings.hubspot.com/progres… #NRF2026 #NRF #retailops #retailtech #retailtraining
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Come visit @Progress4Retail & @WorksmithInc at #NRF2026 Level 3 Booth 3867 to see the future of #retail workforce and workplace management. #nrf #retailtech
Welcome,@mmlafleur 💼✨ The brand built on “taking the work out of dressing for work” is now taking the work out of running #stores with Progress Retail—centralizing #storeops, elevating internal comms, and delivering always-on learning for #retail teams. #nrf2026 #NRF
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Kicking off the new year this week with multiple new #retailers going live with @Progress4Retail in 🇺🇸, 🇨🇦, 🇦🇺! See what all this customer love is about for the #retail ops and #WFM category at @NRFnews in New York next week. Progress Retail & @WorksmithInc at Booth 3867. #nrf
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Empower the people behind every #store. Progress Retail helps #retailers train, engage, and align teams at scale — alongside @WorksmithInc, orchestrating modern #retail operations. See for yourself at @NRFnews Big Show. #Workforce #NRF
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Merry Christmas & Happy Holidays from Progress Retail.
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🤝 Partnership Announcement: Progress Retail x FOURWALL We’re excited to share that Progress Retail is partnering with FOURWALL, aligning #storeoperations and workforce enablement with #retail #realestate intelligence. #CRE
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Welcome, @RebeccaVallance 🤝 The international fashion brand is partnering with Progress Retail to centralise boutique operations, simplify communication, and scale #training with our AI-powered #retail operations platform. We’re proud to help support their growth.
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