Podcasts about avalara

Tourists flew in for the World Cup and went viral filming trips to Buc-ee's and Waffle House. Rick Watson and Jessica Lesesky unpack what that attention is actually worth, then move to two bigger bets.The Watson Weekly Weekend episode is sponsored by Avalara. Its Agentic Tax and Compliance automates behind-the-scenes work for ecommerce brands, enabling accurate checkout tax calculation, clearer tariff and duty visibility, and fewer customer surprises. Avalara integrates with platforms like Shopify, BigCommerce, and WooCommerce. Learn more at avalara.watsonweekly.comOpenAI is selling ChatGPT as an ad platform, with claims of 900 million weekly users and a target of a $100 billion ad business by 2030. The pitch is conversational intent. The problem is everything the older platforms already learned the hard way about guardrails, minors, and regulated categories.Then Shopify Editions Spring 2026, where the catalog is suddenly the whole strategy. Shopify wants to be the feed AI shopping agents read from, and Shop Pay is now available on any platform, anywhere. Rick makes the case that this is Shopify finally aiming at Amazon#watsonweekly #bucees #wafflehouse #worldcup #openai #shopify #ShopifyEditionsSpring2026

Most brands still evaluate enterprise Shopify on license cost. The operators in this conversation evaluate it on opportunity cost, and that reframe changes the whole decision.Rick Watson opens a three-part series on the business case for enterprise Shopify with three people who have actually run the migration. Elara Verrett, Chief Digital and Customer Officer at Reitmans made the move to get closer to the customer without standing up an army of engineers. Renee Halverson, CMO at Marine Layer, has run on the platform for more than a decade and scaled the brand without hiring a CTO to babysit the stack. Scott Lux, VP of Digital Commerce at Stanley 1913, came from the Salesforce and Demandware world and now uses Shopify to survive high-heat drops, where the only question that matters is how many orders per minute the platform can clear.The number that came up: one brand cut its tech partner count from 40 to 10. The argument underneath it: a fashion retailer's core competency is retailing, not running a development shop.It isn't all upside. Scott's warning is blunt. The front end is nimble, but the downstream integrations into OMS and ERP are where "easy" goes to die, so pressure test them before anyone signs. Lara's warning is about people, not software. The agility is real, and most large organizations are not built to absorb it.One point they all landed on, and it cuts against instinct: standardization beats customization where it counts. Checkout is the example. Shoppers trust the flow they already know, and rebuilding it rarely pays for itself.The Big Green Bag Of Promise: Enterprise Shopify Webinar Series is sponsored by Avalara, Domaine, and Pattern.

Shopify wants to be the checkout layer under every AI agent, and its Spring 2026 edition shipped 150-plus updates to prove it. Meanwhile air freight spot rates climbed 41% year over year while demand grew 4%. Somebody is paying for that gap.Shopify Spring 2026: building the plumbing for agents Checkout now runs inside Microsoft Copilot, paid with Shop Pay. There's a universal commerce protocol built with Google. A new agentic commerce plan lets brands sell across ChatGPT and the Shop app without ever being on Shopify. Native B2B is getting pushed down to every plan, aimed at a $36 trillion market. The bet is clear: own the merchant-of-record layer before the agents do.Kimberly-Clark: $3 billion to fix the supply chain Two years into a five-year productivity program. CFO Nelson Urdaneta points to simpler manufacturing, a redrawn distribution network, and more automation. A $1 billion automated DC is going into Beech Island, South Carolina, plus an advanced plant in Ohio. The Kenvue merger closes in the back half and lets them pack trucks tighter by mixing heavy and high-volume goods.Amazon's Peter DeSantis at VivaTech: AI is nowhere near done DeSantis says models need to get 100 to 1,000 times more efficient before they're genuinely useful. The next leap comes from speed: a 40-millisecond reaction time to match human conversation. His fix is a flywheel where chips and models get designed together to drop cost and lift performance.Air freight: 41% up on 4% demand Spot rates hit $3.40 per kilo in May. Surcharges, fuel swings, and Middle East instability are doing the work, not volume. Northeast Asia is up 39%, Southeast Asia up 33%, and Europe to North America has softened. Most of that cargo is data center hardware and semiconductors.The Investor Minute contains 5 stories this week.The Watson Weekly is sponsored by Avalara. It works with platforms like Shopify, BigCommerce, and WooCommerce, helping teams manage compliance faster and scale with confidence. Learn more at avalara.watsonweekly.com.

TikTok Shop moved $4.4 billion in beauty and wellness. Saks wants $9 billion by 2030. Castle claimed $1.4 billion and was worth $16 million. This week is about which numbers actually hold up.Three companies put big figures on the table. Only one of them earned it, and even that one comes with an asterisk. Rick Watson and Nick Kaplan have a thought provoking conversation on these 3 stories. TikTok Shop: reach without trustRoughly $4.4 billion in wellness and beauty sold since the 2023 launchBrand executives call it a "mafia" because of the traffic it forces through them. The honest scorecard is the halo it throws onto Amazon and Ulta, not the checkouts happening inside the appAwareness is the strength. The weakness is trust: missing shipping confirmations, sellers you can't place, a buying experience that still feels provisionalThe Watson Weekly Weekend edition is sponsored by Avalara. Its Agentic Tax and Compliance automates behind-the-scenes work for ecommerce brands, enabling accurate checkout tax calculation, clearer tariff and duty visibility, and fewer customer surprises. Avalara integrates with platforms like Shopify, BigCommerce, and WooCommerce. Learn more at avalara.watsonweekly.comSaks Global: out of bankruptcy, into a targetA Texas court approved the Chapter 11 exit plan. Debt cut 75% to about $1.2 billion$500 million in fresh financing, paired with a mandate to reach $9 billion in GMV by 2030The model that got Saks here is still intact: leveraged, low-margin, carrying expensive real estate. And the vendors who went unpaid earlier this year are not feeling generousCaaStle (Gwynnie Bee): a $1.4 billion fictionThe rental subscription business once known as Gwynnie Bee was sold as a $1.4 billion company. The real number was around $16 millionFounder Christine Hunsicker admitted to securities fraud in MarchThe part that should worry everyone: professional investors and auditors missed invented financials. One investor was reportedly paid off to stay quiet, and audit documents from a recognizable firm were falsifiedWhat ties these together is how cheap a number is to produce and how hard the thing underneath it is to fake. TikTok has the reach but hasn't built the trust. Saks has the target but not yet the model to hit it. CaaStle had neither and sold the story anyway. The question worth sitting with: how many of the valuations you read this week are closer to Saks, and how many are closer to CaaStle?

Salesforce renamed Commerce Cloud to Agentforce Commerce and calls this its biggest release in years. Rebrand, or substance? Nitin Mangtani makes the case.Every enterprise vendor is bolting "agentic" onto its roadmap this year. Salesforce went further and renamed the whole product. Nitin Mangtani, who runs Commerce and Retail Cloud, came on to defend the release line by line.We get into Storefront Next, the new storefront meant to serve both the merchant who wants clicks and prompts out of the box and the developer writing code with AI-native tools. The agentic layer: a search engine built on shopper intent instead of keywords, native chat, a ChatGPT catalog integration going live in June, and a shopper agent that's supposed to behave like the associate you'd get in a good store. The B2B story the B2C headlines tend to bury, including round-trip quoting, multicart, and a buying flow that runs on WhatsApp. And modern POS, where the bet is that systems nobody has rethought in twenty years are finally worth rebuilding.Nitin came in through the PredictSpring acquisition two years ago and ran Google's shopping team back in the early 2000s, so he's watched the discovery layer move before. His line throughout: technology for its own sake is worthless. Tie it to ROI and a better customer experience, or don't ship it.So I pushed on the question every merchant on the platform is actually asking. Hear Agentforce Commerce, Storefront Next, and a ChatGPT integration in the same week, and what changes for you, and how soon? Listen and decide whether the rebrand earns the airtime.The Watson Weekly interview is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com.

This week on the Watson Weekly weekend edition, Rick Watson and Jessica Lesesky discuss: Shopify pushes its buyback to $5 billion while every other tech giant pours cash into AI. We ask the obvious question: built for the AI era, or built for the next earnings call? Then Apple's new Siri arrives at WWDC running on Google Gemini, a roughly $1 billion-a-year arrangement that sits next to the $20 billion Google already pays to be Apple's default search. And Anthropic drops a memo on three possible AI futures on its way to an IPO, with Rick putting the whole thing on an 18-month-to-two-year clock. The Watson Weekly Weekend episode is sponsored by Avalara. Avalara integrates with platforms like Shopify, BigCommerce, and WooCommerce. Learn more at avalara.watsonweekly.com

Software agents are now the highest-converting shoppers on the web, and most stores are built to lock them out. Rick Watson sit down with Stripe's Danny Smith, who leads global agentic commerce solution architecture, to work through what changes when your buyer is a piece of software.The Watson Weekly interview is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com.They cover why agents convert about 4x better than humans, why two-thirds of agent checkouts fail on sites built for people, and the four ways merchants can let agents pay, from approving every purchase by hand up to agents transacting with each other directly. Danny closes with three concrete moves to make now, starting with treating your robots.txt like a doorman instead of a bouncer.

It's June 8th, 2026, and Rick Watson breaks down the week's e-commerce news with his usual habit: put the press release down and look at the calendar.This week: Amazon yanks Prime Day forward to June 23rd–26th and blames the World Cup and America's 250th birthday. Rick isn't buying it. With Q2 closing June 30th and a nervous consumer pulling back, this looks like a P&L decision aimed squarely at Walmart's grocery turf.Then FedEx Freight starts trading on its own as FDXF and the new CEO promises to "leapfrog" the competition. The stock closed down 7% on day one. Rick stress-tests that word against the actual target: 15% operating margin by 2029, up from roughly 12 today. That's catching up, not leaping.This week's episode is sponsored by Avalara. It works with platforms like Shopify, BigCommerce, and WooCommerce, helping teams manage compliance faster and scale with confidence. Learn more at avalara.watsonweekly.com.Plus Anthropic's confidential IPO filing and why "confidentially" is the word everyone's skipping. The growth is real and genuinely insane, but most of the eye-popping numbers are run rate, the real annual figure is $10 billion, and the gross-margin question under 5 gigawatts of Amazon-funded compute is the one nobody can answer yet.And the ShipStation Global merger: WEX and Auctane combine into a 3-billion-shipment Thoma Bravo roll-up. Rick's read on whether welding a freight desk to label-printing software actually holds together.

In this episode of the AI at ViVE series on The Beat Podcast, host Sandy Vance welcomes back Peter Horadan, CEO of Vouched, for a fascinating and forward-looking conversation about one of the most consequential shifts happening in digital identity right now. Digital driver's licenses are no longer a curiosity at TSA checkpoints. They are becoming a global standard, and healthcare is one of the industries that stands to benefit most.  From eliminating duplicate patient records to defending against deepfake fraud to solving the emerging challenge of AI agent identity verification, Peter lays out a clear and compelling vision for what healthcare identity infrastructure needs to look like in the very near future. If you work in telehealth, healthcare IT, compliance, or patient access, this episode will make you think very differently about something most organizations have never considered a strategic priority.  It is believed that about 7% of people in the United States have a digital driver's license today, with estimates reaching 30% adoption by the end of this year and 50% by the end of 2027. If you aren't having conversations for this shift, learn why it matters and how to incorporate it into your patient intake.  In this episode, they talk about: Seven US states are currently issuing digital driver's licenses, and over 30 have  announced plans to do so California has already issued over two million digital driver's licenses, and the EU mandates adoption across all 27 member nations by the end of this year Digital IDs live in a secure chip on your phone, cannot be copied or forged, and require a live biometric to use Between 5 and 15% of electronic health records either have duplicate records for the same patient or multiple patients sharing one record, and strong identity verification at intake is the fix Vouched dramatically reduces patient drop-off rates at the identity verification step, as evidenced by MyStart Health's 40% net business impact Digital IDs actually enhance privacy because they allow users to share only the specific attributes needed, like confirming age without revealing anything else AI agents are already showing up in healthcare workflows, and healthcare organizations need to think now about how to verify that an agent is trustworthy, authorized by a real patient, and actually who it claims to be Vouched released the MCP-I specification a year ago as an open standard for AI agent identity verification, now adopted by the Decentralized Identity Foundation and expanded under the name KYA-OS By the end of 2026, Vouched predicts 40 to 50% of US adults will have a digital driver's license  A Little About Peter: Peter Horadan is the CEO of Vouched, the AI identity verification platform that's transforming how leading Healthcare and Financial Services companies onboard and verify people—instantly and securely. Throughout his career, Peter has led the charge in replacing slow, manual workflows with scalable, automated systems that unlock efficiency, reduce costs, and create measurable impact. From digitizing expense reporting at Concur to streamlining sales tax compliance at Avalara, Peter has helped modernize core business processes across industries. His leadership reflects a deep understanding of how automation can drive growth, compliance, and customer experience at scale. Peter has also held leadership positions at Alavara, Scout Analytics, Microsoft, Corillian, and BEA Systems.

Rick Watson and Jessica Lesesky sit down to unpack a busy stretch across tech, shipping, and commerce. They open with Anthropic's confidential IPO filing, submitted to the SEC on June 1st, and what it signals about the AI lab's trajectory. After a $65 billion Series H that pushed its valuation to $965 billion, Anthropic now sits ahead of OpenAI on that measure, and Rick and Jessica dig into how it got there: a revenue run rate that climbed from roughly $10 billion a year ago to about $47 billion by May 2026, helped by a developer-first bet through Claude Code that has made it a serious contender for enterprise spend.The Watson Weekly Weekend episode is sponsored by Avalara. Its Agentic Tax and Compliance automates behind-the-scenes work for ecommerce brands, enabling accurate checkout tax calculation, clearer tariff and duty visibility, and fewer customer surprises. Avalara integrates with platforms like Shopify, BigCommerce, and WooCommerce. Learn more at avalara.watsonweekly.comFrom there the conversation turns physical. USPS and DHL have signed a multi-year contract valued at well over $10 billion, with DHL handling pickup, sorting, and transport while USPS covers final-mile delivery. It lands at an awkward moment for the Postal Service, which posted a $9.5 billion loss in fiscal 2025 and whose Postmaster General has warned of a possible cash crisis within a year absent action from Congress.The last segment covers Salesforce's push to wake up a commerce cloud that had been growing under 2%. The reported Contentful acquisition (somewhere in the $1 to $1.5 billion range) fits a long pattern that runs through MuleSoft, Tableau, Slack, and PredictSpring. Rick and Jessica close on whether the integrated Agentforce suite can hold up against focused players like Shopify.

Christina Hagopian has spent 24 years running her own brand strategy and creative practice. In this episode she joins Rick Watson to explain why a brand is far more than a logo: it's what people think and feel about you before your message ever lands, and it has to trace back to a company's actual mission, vision, and values.She and Rick talk through the real and the overstated parts of AI in marketing. It earns its keep on brainstorming, competitive audits, brand voice, and rough first drafts of positioning or naming. It falls down on original, trademarkable work because it leans on the average of what's already out there, and Christina describes a case where it couldn't get something as specific as REM sleep brain waves right for a medical site. Her argument: AI replaces average design, not designers.The Watson Weekly interview is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com.The throughline is differentiation. In a crowded digital space, a clear point of view is what gets you noticed, and a strong brand is the foundation everything else stands on. You have one either way. The only question is whether you've built it on purpose.

Rick Watson runs through a busy week in retail. Walmart posted a $177.8 billion quarter, with revenue up 7.3%, U.S. comps up 4.1%, and global e-commerce up 26%, yet free cash flow landed at negative $1.9B as automation capex climbed. Advertising grew 37%, marketplace sales jumped close to 50%, and new shoppers skewed upper-income. At Sam's Club, more trips but smaller baskets.Authentic Brands Group named a new CEO: founder Jamie Salter moved to executive chairman, and former MGM Resorts chief Matt Maddox took over. ABG holds 50-plus brands, $38B in system-wide sales, and 77% of the company behind Saks, Neiman Marcus, and Bergdorf Goodman. Salter floated an IPO within the year.At Google I/O 2026, the Universal Cart follows shoppers across Search, Gemini, YouTube, and Gmail, AI Mode crossed a billion monthly users, and native checkout opened to UCP merchants. Kroger hit $16B in e-commerce with a first profit in sight, wages past $20, two senior exits, and 70 to 80 stores planned. Plus an Investor Minute on Global-e, Insider, and Brown-Forman.This week's episode is sponsored by Avalara. For e-commerce brands, tax compliance grows more complex with every new channel, state, product, and market. Avalara Agentic Tax and Compliance automates the behind-the-scenes work so merchants can offer a smoother checkout, with accurate tax calculations, clearer visibility into tariffs and duties, and fewer surprises when orders arrive. It works with platforms like Shopify, BigCommerce, and WooCommerce, helping teams manage compliance faster and scale with confidence. Learn more at avalara.watsonweekly.com.

Rick Watson and Jessica Lesesky break down Walmart's Q1 numbers and what they say about where retail is heading. Revenue was up 7.3%, U.S. comps rose 4.1%, and global e-commerce grew 26%, but the more telling figures sit elsewhere: advertising up 37% globally and the U.S. marketplace up nearly 50%. Rick and Jessica make the case that Walmart is quietly becoming a digital services business, pulling in wealthier shoppers with celebrity lines and faster delivery, and backing it all with a $1.7 billion-a-year bet on fulfillment automation that Kroger and others will struggle to match.The Watson Weekly Weekend episode is sponsored by Avalara. Its Agentic Tax and Compliance automates behind-the-scenes work for ecommerce brands, enabling accurate checkout tax calculation, clearer tariff and duty visibility, and fewer customer surprises. Avalara integrates with platforms like Shopify, BigCommerce, and WooCommerce. Learn more at avalara.watsonweekly.comFrom there the conversation moves to Google I/O and the "agentic" pitch, including a universal cart meant to follow you across Search, YouTube, and Gemini through Google Wallet. Then the happiness index returns for a look at a K-shaped economy, where affluent buyers keep spending (Amex reported 10% growth in card member spending) while a lot of people are cutting back on basics like gas. Rick closes with advice for brands: shrink the gap between deciding and doing. Take out the friction, lean on convenience and automation, and you win the customer.#WatsonWeekly #Walmart #Retail #Ecommerce #GoogleIO

In this Watson Weekly interview episode, Rick Watson is joined by Lennart Stevens, VP of Product Management for Agentforce Commerce at Salesforce, who walks through Storefront Next, the latest evolution of Salesforce's commerce storefront.Storefront Next is built for developers and for a world where AI and agentic coding are the default. You can spin up a new storefront inside Business Manager with a click-based setup. Under the hood it runs on Salesforce's Managed Runtime as a hosted headless surface, with an enhanced SCAPI layer that lets apps, kiosks, and other channels pull from the same data. The stack standardizes on React, Shadcn, and Tailwind. Existing customers keep their catalogs, prices, and promotions and surface them through the new API.The Watson Weekly interview is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com.Lennart also gets into the agentic tooling (agent shopper, agentic merchandising), quiet AI like product readiness scores that flag missing info without nagging, reusable content blocks and embedded Page Designer components, and turnkey industry templates for retail, cosmetics, and furniture that convert well out of the box. He covers the upgraded CLI, the growing library of skills, and support for UCP as the channel-selling standard.The whole point: cut the standup busywork so developers spend time on what actually moves the business.#watsonweekly #agentforce #storefrontnext #agentic

Two big retail earnings reports, two very different stories. Home Depot grew total sales 4.8% to $41.77 billion, but comparable sales barely moved (up 0.6%) and net income slipped to $3.29 billion from $3.43 billion a year ago, a sign of margin pressure. Target posted the louder top line, with net sales up 6.7% to about $25.15 billion and comps up 5.6%. The catch: net income fell 24% to $781 million, and the stock dropped nearly 5% after management guided comps down to roughly 1% for the rest of the year.On the tech side, Google and Blackstone are launching an AI cloud company with as much as $25 billion behind it, built on Google's own TPU chips to take on Nvidia and CoreWeave. France's Publicis Group bought the data platform LiveRamp for $2.2 billion in cash, a wager on "data co-creation" for AI agents.And 5 Investor minute stories from the world of venture capital, IPOs, and mergers and acquisitions. The Watson Weekly is sponsored by Avalara. For ecommerce brands, tax compliance gets more complicated with every new channel, state, product, and market. Avalara Agentic Tax and Compliance helps automate the work behind the scenes, so merchants can deliver a smoother customer experience — with accurate tax calculation at checkout, clearer visibility into tariffs and duties, and fewer surprises for customers when their order arrives.Avalara works with ecommerce platforms like Shopify, BigCommerce, WooCommerce, and more, helping teams manage compliance faster and scale with more confidence. To learn more about Avalara's ecommerce compliance solutions, and explore resources built for growing ecommerce brands go to avalara.watsonweekly.com for more details.

Home Depot just told the market it's treading water, and Rick Watson and Jessica Lesesky dig into why the remodeling boom never showed up. People are tapping their home equity to consolidate debt, not rip out the bathroom. Paint and outdoor are fine. Lumber, flooring, mill work? Not so much. So Home Depot is quietly walking away from the consumer and betting the house on pros, HVAC, and a $700 billion market.The Watson Weekly is sponsored by Avalara. Its Agentic Tax and Compliance automates behind-the-scenes work for ecommerce brands, enabling accurate checkout tax calculation, clearer tariff and duty visibility, and fewer customer surprises. Avalara integrates with platforms like Shopify, BigCommerce, and WooCommerce. Learn more at avalara.watsonweekly.com.Then: TikTok is now the fourth largest health and beauty retailer in the country at $4.4 billion, and the action isn't even in the videos. It's in the comments. We break down why brands should build the conversation first and let the comment section do the selling.And the one that broke the internet: Everlane sold to Shein for $100 million, down from a $550 to $600 million peak. Common stockholders get nothing. We get into whether Shein actually paid cash for brand equity or just bought itself a respectable-looking front for a not-so-respectable supply chain. Jessica says the quiet part out loud. Rick's head hurts.Plus a quick read on AI maturity from The Lead conference floor, and why the people who are most "AI-pilled" somehow ended up busier than ever.#watsonweekend #homedepot #remodel #tiktok #comments #everlane #shein

This week we had the exciting opportunity to travel to Anchorage, Alaska, to participate in the Fifth Annual Alaska Sustainable Energy Conference. The conference convenes researchers, industry leaders, entrepreneurs, policymakers, and investors to discuss the future of energy development, infrastructure, technology, and resource leadership across Alaska and the broader global energy landscape. We had the honor of moderating a discussion featuring Governor Mike Dunleavy and Chairman of the National Energy Dominance Council and U.S. Secretary of the Interior Doug Burgum. Given Alaska's strategic importance across energy, critical minerals, infrastructure, and geopolitics, it was a fascinating and timely discussion. In our conversation, Governor Dunleavy emphasizes the dramatically improved partnership between the federal government and the State of Alaska under the current Administration, contrasting it with prior years when Alaska faced significant federal restrictions on development. Drawing on their experiences leading major energy-producing states, Governor Dunleavy and Secretary Burgum reflect on the operational, economic, and political realities of energy development and infrastructure investment. They walk us through renewed lease sale activity, rising investor interest in Alaska, and the broader role Alaska could play in supporting U.S. energy dominance and Western Hemisphere energy security. We explore the increasing importance of affordable, reliable, and secure energy in attracting manufacturing, AI infrastructure, and industrial investment, as well as the rapidly growing electricity demand tied to data centers and advanced technologies. Secretary Burgum provides an overview of the Administration's efforts to accelerate permitting reform and reduce regulatory bottlenecks, including examples of projects receiving approvals in weeks rather than years. We touch on domestic mining and critical mineral development, LNG exports, the role of nuclear, hydro, geothermal, and natural gas in future energy systems, and the Administration's broader push to accelerate infrastructure and resource development across the United States. We cover the transformational potential of the Alaska LNG project, the growing energy needs of U.S. allies across Asia, the importance of codifying regulatory and permitting reforms for long-term investment certainty, and why Governor Dunleavy and Secretary Burgum both believe Alaska is entering a new “golden age” of development and opportunity. Thank you to Governor Dunleavy for inviting us and to Secretary Burgum for joining us for a thoughtful discussion on the future of Alaska, energy, and American economic development and energy security. About Governor Mike DunleavyGovernor Mike Dunleavy arrived in Alaska in 1983 as a young man looking for opportunity, and he found it. His first job was working in a logging camp in Southeast Alaska. Later on, Governor Dunleavy earned his teacher's certificate, and then a Master of Education degree from the University of Alaska Fairbanks. He spent nearly two decades in northwest Arctic communities working as a teacher, principal, and superintendent. Governor Dunleavy and his family moved to Wasilla in 2004, where he owned an educational consulting firm and worked on several statewide education projects. Dunleavy served on the Mat-Su Borough School Board, with two years as Board President, and then as a state senator for five years. Dunleavy was first elected Governor in 2018 and then again in 2022. Governor Dunleavy has kept the health of the economy and jobs at the forefront of his Administration's policy setting initiatives and has been a true champion for the Alaskan business community. Governor Dunleavy's wife Rose is from the Kobuk River Valley community of Noorvik. Together, they have three children who were raised in both rural and urban Alaska. Governor Dunleavy is focused on moving Alaska forward and believes that our greatest years are yet to come if we work together to maximize our potential. About Secretary Doug BurgumDoug Burgum is the 55th Secretary of the U.S. Department of the Interior. Raised in Arthur, North Dakota, Burgum worked as a chimney sweep to help pay his way through North Dakota State University before earning an MBA from Stanford University. In 1983, Doug literally “bet the farm” to provide seed capital for a software startup called Great Plains. Doug led Great Plains through a successful IPO and grew the company to over 2,000 employees before its acquisition by Microsoft. Burgum remained with Microsoft for six years as the Senior Vice President of Business Solutions. Doug later co-founded Arthur Ventures and served as chairman for international software companies including Atlassian, SuccessFactors, and as a board member for Avalara. In 2016, Burgum was elected to serve as North Dakota's 33rd Governor. In 2020, he was re-elected in a landslide. Under his leadership, North Dakota passed the largest tax cut in state history and dramatically reduced red tape. As a testament to Burgum's leadership, Forbes named him “America's Best Entrepreneurial Governor.” During his tenure, North Dakota experienced the highest growth in real GDP and had the lowest unemployment rate in the country. Burgum has three adult children. He is married to Kathryn Burgum, a nationally recognized advocate for addiction recovery. We hope you enjoy today's discussion as much as we did. This certainly won't be our last trip to Alaska. Our best to you all!

The Watson Weekly for May 18, 2026. Amazon launched a 30-minute delivery to take on DoorDash. eBay shuts down GameStop's bid. OpenAI puts $14 billion behind an enterprise AI play. The Watson Weekly is sponsored by Avalara. For ecommerce brands, tax compliance gets more complicated with every new channel, state, product, and market. Avalara Agentic Tax and Compliance helps automate the work behind the scenes, so merchants can deliver a smoother customer experience — with accurate tax calculation at checkout, clearer visibility into tariffs and duties, and fewer surprises for customers when their order arrives.Avalara works with ecommerce platforms like Shopify, BigCommerce, WooCommerce, and more, helping teams manage compliance faster and scale with more confidence. To learn more about Avalara's ecommerce compliance solutions, and explore resources built for growing ecommerce brands go to avalara.watsonweekly.com for more details.Amazon Now is live. Thirty-minute delivery for groceries and household essentials, starting in Atlanta, Dallas, Fort Worth, Philadelphia, and Seattle, with seven more cities queued up. Prime members pay $3.99 an order. Non-Prime pays $13.99. The strategy is direct. Smaller fulfillment centers in residential zones, aimed straight at DoorDash, Uber Eats, and Instacart.eBay's board said no to GameStop. Chairman Paul Pressler called the unsolicited bid "neither credible nor attractive." The rejection wasn't really about price. OpenAI launched the OpenAI Deployment Company, valued at $14 billion, with $4 billion freshly raised under TPG's lead. The investor list reads like a consulting roster: McKinsey, Bain, Capgemini. The mission is forward-deployed engineers embedded inside enterprises to rebuild workflows. We also break down the Watson Weekly's Shopify three-part June webinar series, The Big Green Bag of Promise, with operators from Stanley 1913, Reitmans, and Marine Layer talking honest numbers on enterprise migration. The webinars are not sponsored by Shopify but by Avalara, Domaine, and Pattern, Register here: https://streamyard.com/watch/ibqNx46Z88BfAnd the Investor Minute: Co-pilot Kit ($27M for an AGUI protocol), Cognizant's roughly $600M Australian acquisition, District's $14.7M seed for community marketplaces, Recharge buying Skio for $105M, and PayPal splitting into three new business units.

Three retail moves worth talking about this week.Amazon is retiring the Rufus name. The shopping chatbot has hit roughly 300M users since its 2024 beta, but Amazon is folding the whole thing into Alexa and calling it "Alexa for shopping." We get into why that branding choice is risky given Alexa's history with kids accidentally ordering things and the privacy lawsuits, and what it signals about an "Alexa for healthcare" or "Alexa for law" coming next.The Watson Weekly Weekend edition is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.comThen GameStop's Ryan Cohen and his $56 billion unsolicited bid for eBay, half cash, half stock. The eBay board's response was a 216-word letter calling the offer "neither credible nor attractive." We dig into whether Cohen ever expected a yes, or whether the whole thing was theater aimed at GameStop's stock price and the $100 billion valuation target tied to his own bonus plan.Finally, Lululemon. Heidi O'Neill, 30 years at Nike, took the CEO job on April 22. Founder Chip Wilson is already on record saying she's not the transformation the company needs. We talk about why Alo Yoga and Vuori are pulling away on the celebrity side, why the men's line feels over-assorted, and what it means when Amazon, Costco, and Target all stock convincing dupes of your core product.

Rick Watson talks with Alan Gaffney (CEO, Townchest), Nick Boetcher (Avalara), and Justin Samakow (Mirakl) about what breaks when a marketplace scales.Townchest runs a "shopping for good" program where schools partner with manufacturers to fund themselves through retail sales. A regional launch created nationwide Nexus exposure within weeks, because supporters of a school in Ohio live in Texas, California, and everywhere else. Alan unpacks the hybrid seller-of-record setup that followed: Townchest carries that role for some partners, not others, and the operational cost runs both ways.Justin and Nick cover the back-end. Mirakl's Catalog Transformer normalizes supplier data and pushes it into thousands of school storefronts. Avalara's Avi agent assigns tax codes from a global library against the data Mirakl sends through. The two also get into where strict SLA automation earns its keep (auto-deactivating sellers who miss order acceptance) versus where alerts suffice (high return rates).The Private Storefronts, Shared Suppliers, One Compliance Nightmare webinar was sponsored by Avalara and Mirakl.

Shopify posted its strongest quarter in four years and the stock fell 7%. Rick walks through why Wall Street wasn't impressed, what the LVMH signing actually means for the "Shopify is only for startups" narrative, and the credit-loss line item that's quietly getting bigger.Also this week:Amazon Q1: three numbers Wall Street missed, including a $150B grocery run rate and free cash flow down 95%The Watson Weekly is sponsored by Avalara—the agentic AI platform automating global tax and compliance for leading eCommerce brands. Go to avalaratax.watsonweekly.com for more details.Alphabet's Universal Commerce Protocol, now signed by Kingfisher, Target, and WayfairGameStop's $55.5B bid for eBay, with Ryan Cohen pitching it as "Chewy on steroids"Investor Minute: PayPal restructure, Recharge buys Skio for $105M, Cognizant grabs Astreya for $600M, Lipton takes a $245M CVC investment, District raises $14.7M seed

Three stories on the table this week, and none of them small.Saks Global plans to exit Chapter 11 on June 22nd carrying $1.2 billion in debt, with a reorganization plan targeting $9 billion in GMV by fiscal 2030. That's nearly double where they sit today. Rick Watson and Jessica Lesesky walk through the vendor mess (720 brands stopped shipping at the worst of it), the repair work underway, and why exiting bankruptcy this leveraged sets up another round of trouble down the road.The Watson Weekly Weekend edition is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.comOver at Victoria's Secret, Australian investor Brett Blundy's BBRC Worldwide has built a roughly 13% stake and is pushing to remove two directors: chair Donna James and Miriam Naficy. The complaint is acquisitions like Adore Me. CEO Hillary Super is running a "path to potential" plan built around body positivity and a return to the Angels heritage. Fiscal 2025 sales are up 5%. The question is whether that's enough to keep the activist quiet.Then earnings. Alphabet did $109B in Q1, with Google Cloud growing 63% YoY to a $20B run rate and a $462B backlog. Amazon hit $181B, AWS grew 28% to $37.5B, and the chip business crossed a $20B run rate of its own. Shopify cleared $100B in quarterly GMV for the first time, with operating income up 88% on the back of all the layoffs and restructuring.The thread underneath all of it: AI compute is getting more expensive, not less. The pricing power is sitting with the infrastructure layer. Amazon, Nvidia, and the LLM owners are collecting the rent. The businesses adopting AI are paying it.

Rick Watson sits down with Mike Hogenmiller, who has spent more than forty years inside home improvement retail and watched the consumer reinvent themselves at least three times.Mike was at The Home Depot in 2001 when the company quietly acquired a 4,000-customer wholesale distributor in Baton Rouge, LA called Your Other Warehouse. That distributor was, at the time, Amazon's biggest and most profitable home-improvement supplier. The acquisition (plus a later decision to stop opening new stores and make existing assets more productive instead) is how Home Depot got roughly 15 years ahead of its closest competitor on digital fulfillment without ever calling it e-commerce.The Watson Weekly interview is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com.The story Mike tells about then-CEO Craig Menear is the part most people miss. Home Depot wasn't building an e-commerce business. They were building commerce. The customer decided what they bought, when, where, and how it arrived. Everything else followed from that.We also get into:• Why Walmart's culture survives and Target's didn't • The Sprouts problem and what happens when a specialty grocer stops buying with confidence • Why every "Amazon of [insert vertical]" pitch ignores the customer • Where CPG brands keep going wrong inside the store • The advice Mike gives DTC founders thinking about their first physical stores

H&M just listed on a US online marketplace for the first time, and they picked Nordstrom. Rick Watson and Nick Kaplan break down what that signals about both brands, and why marketplaces with no inventory commitment keep working when standalone marketplaces keep dying.Next up, GLP-1 hits the bridal industry. 10% of couples planning weddings this year are on a GLP-1, and more than half started the medication specifically for the wedding. Some users drop a clothing size every two to three weeks, which is a problem when a wedding dress takes nine months and costs five figures. Bridal shops are now asking buyers to sign waivers. Rick and Nick widen the conversation into plus-size assortments, the longevity boom in CPG, and why protein and creatine are having a moment.The Watson Weekly Weekend edition is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.comThen the big one: the e-commerce organization of the future. Unilever cut from 3,000 agencies to under 800, saving half a billion dollars. P&G in-housed media for $750M in fee reductions. A retail "season" is now two weeks. Where does the merchant sit in all of this, and is ChatGPT a better buyer than a human? Nick argues the merchant role contracts but never disappears. Rick pushes on whether the 2026 merchant is really just one person editing algorithms instead of product.Subscribe to the Watson Weekly newsletter at watsonweekly.com.

What does B2B digital transformation look like when your end user is an HVAC contractor standing on a rooftop in 95-degree heat? In this episode of The Watson Weekly, we sit down with Lindsay Althouse(Johnstone Supply), Bryan House (Elastic Path), and Lee Trotter (Data Realm) for a candid panel discussion on modernizing legacy B2B businesses without breaking what already works.Johnstone Supply—a $4 billion HVAC distributor with 450 stores—offers a fascinating case study in real-world transformation. After shifting from a co-op model to an LLC, the company faced a daunting challenge: building a unified digital experience on top of 72 store groups, each running its own ERP system. Lindsay walks us through how a headless commerce architecture made a modern mobile app possible, why deep customer discovery (including interviews with contractors in the field) shaped every design decision, and how a phased alpha-to-beta rollout helped them validate the product with real users.The conversation also dives into Johnstone's AI assistant rollout, where the stakes go beyond bad recommendations—suggesting the wrong furnace part could cause physical harm. Lindsay explains why they chose a private LLM in a restricted environment, limited to verified product data, to keep trust and safety at the center.This B2B webinar is sponsored by Avalara , Elastic Path , and Data Realm.Beyond the case study, the panel unpacks the strategies that separate successful B2B modernization from expensive failures:Why customer-centric design beats feature checklists every timeHow commerce platforms can abstract legacy ERP complexity without a rip-and-replaceChange management tactics for aligning sales teams with digital channels (hint: give reps credit for digital orders)Why every project decision should ladder up to a clearly defined goalWhether you're leading a digital transformation, building B2B products, or just curious about how a 70-year-old distributor competes with Amazon-era expectations, this conversation is packed with practical insight.#B2BCommerce #DigitalTransformation #HeadlessCommerce #HVAC #UX #AI #WatsonWeekly

This week on the Watson Weekly, Rick Watson breaks down the biggest stories shaping commerce, technology, and AI infrastructure.Tim Cook is stepping down as Apple CEO after 14 transformative years that took the company from a $300B market cap to $4 trillion. John Turnis takes the helm September 1st.The Watson Weekly is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.comAnthropic just inked a $100 billion, 10-year infrastructure deal with AWS for 5 gigawatts of compute, while Amazon pours another $5B (potentially $20B more) into the AI lab. Brad Jacobs strikes again: QXO is acquiring Top Build for ~$17B, his third deal in under a year.Plus, a tribute to industry leader Jon Panella.The Investor Minute with 5 items this week from the world of venture capital, acquisitions, and IPOs.

On this weekend edition of The Watson Weekly, Rick Watson and Jessica Lesesky break down the biggest stories shaping tech, retail, and AI.Amazon is doubling down on its Anthropic bet — with a new deal that has Anthropic committing $100B to AWS over the next decade, while Amazon pumps in an additional $5B(with up to $20B more on the table) and locks in guaranteed compute capacity. With over 100K customers already using Claude on Bedrock and Amazon holding a reported 15% stake, this partnership is reshaping the cloud AI landscape.Home Depot quietly acquired SIMPL Automation, a scrappy robotics startup that had raised just $100K before piloting its warehouse density technology at Home Depot's Locust Grove DC. Rick and Jessica unpack what this signals about the arms race between Home Depot and Lowe's to modernize supply chain and distribution.The Watson Weekly Weekend edition is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.comPlus, the end of an era at Apple: Tim Cook is stepping down as CEO after 15 years to become executive chairman, handing the reins to 25-year Apple veteran John Ternus. Cook leaves behind a company transformed — from a $350B market cap to $4T, and a services business that now tops $100B. What does a hardware-focused CEO mean for Apple's AI strategy and search partnerships?

When Helen Lo founded Lo & Sons at 65, she was solving her own travel problem. Fifteen years later, her family-run DTC brand is navigating one of the toughest environments in consumer goods: a flood of dupes, shrinking development windows, and a rapidly shifting AI landscape.Rick Watson is joined by Katie Omstead, President at Lo & Sons, and Sonal Gandhi, Chief Content Officer at The Lead. The Watson Weekly interview is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com.In this Watson Weekly interview, we dig into how Lo & Sons compressed its product development cycle from two years to nine months (with four to five months on the horizon), why 90% of the business remains direct-to-consumer, and how AI is reshaping everything from ideation to inventory. We also preview The Lead, the commerce summit landing in New York on May 20–21, where 3,000 operators and 150 speakers will gather — no vendor spin, just real talk on building brands in 2026.

Today on the Watson Weekly: Google treats compute like a moat, Amazon finally figures out groceries, Vinted runs the Amazon playbook in Europe, Apple shows up late to the glasses party — and finally, The Investor Minute with 5 items this week from the world of venture capital, acquisitions, and IPOs.The Watson Weekly is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.comGoogle's Compute Discipline — Compute isn't just infrastructure anymore, it's the moat.Amazon's Grocery Crystallizes — The 2025 shareholder letter dropped a $150 billion gross grocery number. Vinted's Breakout — 47% GMV growth to €10.8 billion. Apple's Glasses Play: Late but Lethal

Rick Watson and Jessica Lesesky break down three stories reshaping the consumer and tech landscape. First, why GLP-1 drugs like Ozempic, Wegovy, and Mounjaro are expected to unlock $13B in new retail spending — and which brands stand to win as 80% of users size down. Then, Nike's latest innovation shake-up: new chief Andy Caine steps in as the stock slides 32%, with Project Amplify, Nike Mind, and Aerofit on the horizon. The Watson Weekly Weekend edition is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.com/Finally, Amazon's $200B and Google's $185B infrastructure bets — and why Sundar Pichai spends an hour a week personally rationing compute.Subscribe to the newsletter at watsonweekly.com.

The Agentic Debate Series Lunch @ Shoptalk Las Vegas 2026, Presented by Logicbroker. Recorded live in Las Vegas on March 24, 2026. Rick Watson hosts an agentic commerce debate with three retail practitioners who aren't selling anything — just calling it like they see it.Chris Silver (CTO, JustFoodforDogs), Gina Lombardo (VP of Digital, Retrofête), and Dave Finnegan (Managing Director, BlackFinn Partners) go head-to-head on three questions the entire industry is dancing around:Will ads ever work inside AI agents — or does injecting ads into a trusted conversation destroy the whole model? Is agentic commerce actually going to drive incremental revenue, or is it a hype cycle with a nice deck? And the big one: are websites doomed when an AI agent can just buy for you?The answers are more nuanced — and more honest — than what you're hearing from the main stage. Topics include cost-per-action ad models, why "retail therapy" isn't going away, how luxury brands could use agents to increase AOV, the consumer trust crisis around hallucinations, and why your product data strategy matters more than your payments infrastructure right now.If you're a merchant trying to figure out what to actually do about agentic commerce in 2026, this is the conversation.The Agentic Debate Series Lunch @ Shoptalk Las Vegas 2026, Presented by Logicbroker, was sponsored by Logicbroker, Avalara, SCAYLE, and Fortier.Timestamps0:00 - Introduction01:45 - Rick Watson setting the scene/background05:10 - Panel members welcomed07:35 - Will ads ever work in a trusted medium?24:43 - Sponsor message from Logicbroker CEO Omar Qari24:13 - Agentic commerce: a nothingburger or incremental?49:38 - Sponsor message from SCAYLE Commerce Engine, Jake Wright52:07 - Are websites doomed?#watsonliveatshoptalk #agenticcommerce #nothingburger #advertising #website

Amazon cuts USPS volume, BNPL shapes where Gen Z gets their teeth cleaned, and why your product data is now an AI infrastructure problem.This Watson Weekly episode covers: The Amazon-USPS tentative deal and what a 20% volume reduction actually signals about Amazon's logistics endgame. The Watson Weekly is sponsored by Avalara - the agentic AI platform automating global tax and compliance for leading eCommerce brands. For more details: https://avalaratax.watsonweekly.comNew April 2026 data on Buy Now Pay Later — not an acquisition tool, a retention weapon. Walmart-backed Eko and the quiet war for AI-ready product catalogs. How Revolve turns an absurd return rate into a full-price sales machine. The Investor Minute with Accenture's Ookla acquisition, ProfitMind's Series A, Lio's $30M procurement automation raise, and OpenAI buying Promptfoo.

Rick Watson and Jessica Lesesky break down three retail stories that challenge conventional wisdom this week.Revolve runs a 60% return rate — triple the online average — and just posted a 60% profit surge. They explain how baking return costs into margins and offering frictionless two-day shipping produces 80% full-price sell-through and a customer base that treats their bedroom like a fitting room. Physical storefronts in Aspen and LA are next.The Watson Weekly Weekend edition is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/Lowe's just launched Home Care Plus: $99 a year gets you two Red Vest associate visits for dryer vent cleaning, HVAC filter swaps, smoke detector batteries, and water heater flushes. The real story is what Lowe's gets in return — appliance age data and a direct line to upsell the aging homeowner market.And Buy Now, Pay Later is no longer just a checkout option. Millennials and Gen Z are 13x more likely than Baby Boomers to choose a merchant based on available financing. Fifty-five percent of Gen Z say installment options influence their choice of healthcare provider. BNPL is now a customer acquisition channel — and merchants paying 4.5–5% in fees may be getting the better end of the deal.

Rick Watson breaks down four stories shaping e-commerce and retail this week: Shopify's partner town hall reveals a company that treats API chaos as a brand attribute — and why that's a problem for any hyperscaler ambition. Lowe's bets $99 can put a red vest inside your home twice a year, and why that physical touchpoint is worth more than any app can replicate. The Watson Weekly is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/USPS wants an 8% fuel surcharge — the first in its history — and what the gap between that and Amazon's 3.5% tells you about structural efficiency. And Allbirds is done: not restructuring, not pivoting — dissolved, with a $4 billion brand selling for $39 million. Plus the Investor Minute: Zipline's $200M Series H, Cintas acquiring UniFirst for $5.5B, OpenAI snapping up Astral, Puratos buying Dawn Foods, and why Bark isn't going private yet.

Apple just turned 50. Amazon quietly acquired two robotics companies. And Allbirds — once valued at $4B— sold for $39M. Rick Watson and Nick Kaplan work through what these three stories have in common: the relentless pressure to find a next act before the first one runs out.The Watson Weekly Weekend edition is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/Topics this week: whether Tim Cook's Apple needs a visionary or just needs to win in AI, what Amazon's Rivr and Fauna acquisitions tell you about where last-mile delivery is actually going, and why Allbirds is a cautionary tale that applies to almost every DTC brand built on a single product. Plus: ambient AI through AirPods, the Rounders theory of the AI market, and why Rick switched from ChatGPT to Claude.Subscribe for weekly retail and commerce analysis: watsonweekly.com

Rick Watson is out. Nick Kaplan is in — and he's not giving the mic back.In this special Kaplan Wednesday episode, Nick takes the research prompts Watson built for his agentic commerce analysis and turns them on the very stories they were designed to interrogate.On the docket: Adyen's white paper claiming infrastructure is the constraint on agentic commerce (it isn't — and their own 95% AML false positive rate says why). Shopify's one-toggle Agentic Storefront promise and the data ownership problem it quietly creates. Klaviyo and Reebok Europe's Locale Aware Catalogs announcement — and the 149,999 merchants who aren't Reebok. The EU AI Act, which starts enforcement in five months and would like a word with every agentic protocol on the market. And the number that breaks every GMV projection: only 14% of shoppers trust AI recommendations enough to transact.The Kaplan Weekly is sponsored by Avalara. — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/The constraint isn't infrastructure. It's trust. Build that first.Happy April Fools. Rick will be back next week.Subscribe for weekly retail and commerce analysis: watsonweekly.com#ecommerce #kaplanwednesday #AIact #watsonwednesday

Live from the chaos of Shoptalk 2026 — where every booth promised an AI future and the floor proved retail is still fundamentally a contractual promise to a customer. Retail and e-commerce influencer Rick Watson is out on assignment in Las Vegas.This episode cuts through the agentic commerce noise. We get into what AEO (Agentic Commerce Optimization) actually requires operationally, why Shopify continues to eat the market while facing real limits at enterprise scale, and what the Stripe-Shopify relationship tells you about where payments infrastructure is heading.The Watson Weekend is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Plus: the honest conversation about AI ads, MCP protocols, and why building an AI Council too early might be the fastest way to slow your company down.Fix your margin problem first. Agentic commerce will not rescue a broken business model — it will just surface the damage faster.Subscribe to the Watson Weekly newsletter: https://www.watsonweekly.com

Darren Heaphy has spent his career at the intersection of e-commerce and logistics — AOL, Scurry, and now eDesk, where he leads product. His take on AI-driven support is blunt: brands are holding AI to a standard they never applied to their seasonal hires, and that double standard is costing them.In this episode, Rick Watson interviews and discusses the real shift happening in customer support — not chatbots replacing agents, but human teams moving from execution to orchestration. Darren calls it the "digital colleague" framework: start AI on low-risk work, build trust through auditability, and expand its scope as it earns it.The Watson Weekly interview is sponsored by Avalara — automated tax compliance built for Shopify merchants, from calculation to returns. For more details: https://avalara.watsonweekly.com/We also dig into a number most brands are sitting on without realizing it: 30–40% of support tickets are pre-purchase questions. Not complaints. Buying signals. And AI can convert those around the clock.What you'll hear:Why AI mistakes feel scarier than human mistakes — and whether that fear is rationalThe "glass box" approach to AI transparency that actually builds team trustHow support roles are evolving from typing to judgmentWhy the fundamentals — speed, accuracy, reduced uncertainty — haven't changed and won'tIf you've been watching AI take over the support conversation and wondering where your team fits, this one's for you.#CustomerSupport #AIinEcommerce #watsonweekly #interview

Dollar stores are quietly winning, Prime Day is jumping the calendar, and the AI arms race just hit its first major reboot. Rick Watson and Jessica Lesesky break down what actually moved this week in retail and commerce.Dollar General doubled its operating profit, Dollar Tree shed Family Dollar and beat estimates, and Five Below kept growing — while 99 Cents Only filed for bankruptcy. The value shift is real, and it's not just low-income shoppers driving it.Amazon is moving Prime Day to June. Is this a Q2 earnings play, a back-to-school land grab, or both? And what does that mean for Walmart, Target, and everyone else chasing the same wallet?The Watson Weekly Weekend edition is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Then: the agentic reboot. Adyen's co-CEO drops a white paper on infrastructure problems in agentic commerce. OpenAI's applications chief reportedly called a "code red" on internal focus. Amazon is adding senior engineer oversight to rein in autonomous code. Anthropic is quietly picking up enterprise market share — and OpenAI's people. Rick's verdict: we are in the early innings, and the wholesale strategy changes are just beginning.Chapters00:00 — Welcome & Intro01:14 — Dollar Store Earnings: Why Dollar General, Dollar Tree, and Five Below are winning — and who isn't04:24 — Amazon Prime Day Moves to June07:23 — The Agentic Reboot: Adyen's white paper, OpenAI's "code red," Anthropic's enterprise surge, and what it all means for brands building on AI

Tom Schmitt is CEO of Radial, North America's largest third-party fulfillment provider — and a company about to become something bigger. As part of the Bpostgroup's rebranding to Paxon, Radial is merging with its sister companies into a single global logistics brand built on decades of e-commerce infrastructure.The Watson Weekly is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Tom sat down with Rick Watson to talk about what he's actually seeing on the ground as AI enters supply chain — and the answer is more nuanced than most headlines suggest.Three things worth your time from this episode:The trust gap is real and measurable. Radial surveyed 1,000 US consumers: nearly two-thirds are uncomfortable sharing payment information with AI agents. That's not a technology problem — it's a brand problem operators need to solve first.Most AI projects are failing their ROI test right now — and that's expected. Tom's crawl, walk, run framework isn't a hedge; it's a diagnosis. Demand forecasting and pick-path optimization have measurable returns today. Fully autonomous warehouse orchestration does not — yet.Agentic commerce has a data standards problem nobody is talking about. Radial is a founding member of ONX — the Order Network Exchange — an open industry standard for how order, inventory, and fulfillment data moves between systems. Agentic commerce only works if agents read the same language. That work is already underway.Plus: the history of GSI Commerce, how Michael Rubin invented the direct-to-consumer industry, and why Fred Smith's old line about FedEx still tells you everything about where supply chain AI is headed.Subscribe to the Newsletter: Get it at https://www.watsonweekly.com/subscribe

Stripe just released an Agentic Technology Suite and positioned it as the infrastructure layer for the next era of commerce.]So who is Stripe actually building this for?The Watson Weekly Interview is sponsored by Avalara. For more information on Avalara, visit - https://avalara.watsonweekly.com/Salesforce Marketing Cloud posted -1% growth in Q4 FY2026 — the end of four years of deceleration and the start of something worse. Rebranding to Agentforce doesn't fix a product growth problem, and acquisitions are a slower fix than they look.The Watson Weekly is also sponsored by Mirakl. You don't need another tool; you need a growth partner. The Mirakl platform is powering the next era of retail for brands and retailers who are ready to move, powered by AI and built for what's next.Costco reported $2B in revenue, up 13.8%, driven by a limited SKU model and a merchandising strategy that creates genuine discovery. Digital is working too — personalized carousels drove $470M in e-commerce sales. The CEO is watching tariffs closely for the next 150 days.And the big structural story: retail's share of total consumer spending dropped from 34.3% in 2022 to 30.8% in Q4 2025. Amazon is absorbing the majority of what remains. The market is consolidating around Walmart and Costco for necessities and Amazon for everything discretionary — leaving mid-market and specialty retail in a structurally difficult position.Investor minute covers 5 stories from the world of IPOs, funding, private equity and more.#watsonweekly #stripe #costco #salesforcemarketingcloud #walmart #amazon

In this week's Watson Weekly weekend edition, hosts Rick Watson and Jessica Lesesky talk about Dick's Sporting Goods' viral Move moment, Elliott Hill in the New York Times, and the gap between consumer spending at Amazon and Walmart. Dick's Sporting Goods is number three in the App Store. Nike is running a PR campaign dressed as a turnaround. And the consumer spending data has already picked the winners of the next decade of retail — most people just aren't reading it correctly.The Watson Weekend edition is sponsored by Avalara. This week: what Dick's Move app gets right that every other retailer gets wrong about loyalty, why Elliot Hill's "innovation platforms" are a story for investors and not consumers, and what a nine-point drop in retail's share of consumer spending actually means for Amazon, Walmart, and everyone else fighting for what's left.The short version: utility beats AI features. NPS doesn't fix itself with a robot shoe. And if you're not Amazon or Walmart, you need a reason to exist — not a broader assortment.#watsonweeklyweekend #dickssportinggoods #nike #amazon #walmart

The AI shopping revolution is here — but who actually controls it? In this week's Watson Weekly, Rick Watson breaks down four stories reshaping the future of e-commerce.The Watson Weekly is sponsored by Avalara. For more information on Avalara visit - https://www.avalara.watsonweekly.com/

Welcome to this weekend edition of Watson Weekly with Rick Watson and Jessica Lesesky! Today, we're breaking down the biggest moves in retail and e-commerce from the past week..We start with Target's latest earnings, where a 1.7% dip in net sales has triggered a major turnaround strategy focused on beauty, food, and the Target Circle 360 premium membership. Then, we dive into Shopify's investor event to discuss Agentic Commerce—is AI the new front door for online shopping? Finally, we analyze the massive $50 billion investment/partnership between Amazon and OpenAI. Why is Amazon mandating the use of its Trainium chips, and what does this mean for the future of AWS?The Watson Weekly Weekend edition is sponsored by Avalara.Key Chapters0:00 - Introduction 0:49 - Target Earnings: Sales Slump & The 2026 Turnaround 6:09 - Shopify's Agentic Commerce Front Door 9:50 - Amazon & OpenAI: The $110 Billion Funding Round #retailtech #Amazon #OpenAI #Shopify #TargetEarnings #EcommerceNews #AICommerce #AWS #WatsonWeekly

Avalara's Chief Architect Tim Diekmann reveals how AI and agentic technology are transforming tax compliance and accuracy across 40,000 jurisdictions leveraging AWS.Topics Include:Avalara provides tax compliance software across North America, Europe, and beyond.They operate between commerce and government, covering 40,000+ jurisdictions.Services span registration, sales tax calculation, and certificate management.Avalara was the only company keeping pace with rapid tariff changes.AI is used to parse unstructured documents like tax notices and publications.Intelligent mapping automates ERP integration across vastly different system configurations.GenAI lets customers query billions of transactions using plain conversational language.Avalara and AWS are now engaged in a promising co-selling motion.Time-to-go-live and transaction accuracy are the key success metrics tracked.Amazon Q was rolled out company-wide, achieving 95% developer adoption.AI literacy is now prioritized across legal, HR, and engineering teams alike.Agentic AI will embed Avalara directly inside customer ERP systems going forward.Participants:Tim Diekmann – SVP of Engineering, Chief Architect, AvalaraSee how Amazon Web Services gives you the freedom to migrate, innovate, and scale your software company at https://aws.amazon.com/isv/

This episode is sponsored by Avalara. Every year brings tax changes at the local, state, and national level, and Avalara has captured the latest updates in their newest tax changes report, which is available now. Avalara's vice president of government relations, Scott Peterson, joins us to discuss some of the report's findings and major themes, including what Scott calls 'off the charts' levels of change in terms of transaction taxes in the US. At the federal level, income tax changes are set to have a direct impact on state income taxes ,and Scott explains how states will react based on own funding needs.  And we discuss why states are expanding their sales tax base into digitawl good and servicees, including taxing digital equivalents and B2B services. Scott also shares his guidance on the role of AI in international tax compliance and what our listeners can take away from this year's report. To learn more, contact Avalara: microsoft@avalara.com.

Is retail suffering from "buzzword fatigue"? In this 25-minute deep dive, Nick Kaplan and Rick Watson debrief the biggest themes, surprises, and reality checks from NRF 2026: Retail's Big Show. From the noise surrounding "agentic commerce" to the practical startups actually moving the needle, we break down what brands need to know to survive the next era of retail.Key Takeaways:The Buzzword Barrier: Why brands are feeling lost in a sea of repetitive jargon and how to spot the difference between hype and high-impact tech.Practical Innovation: A look at the NRF Innovation Hub, featuring startups like Marpipe that are solving real-world problems in product feed and ad optimization.The Virtue of Patience: Navigating the rapid release cycle from giants such as OpenAI and Google requires a steady hand and a long-term view.The NRF Debrief is sponsored by Avalara and Freshmint.

Damien Martin and Tony Nitti of EY analyze the first three of their top six tax cases from 2025, focusing on what constitutes income in CF Headquarters Corp. v. Commissioner, Franklin v. Commissioner, and Feige v. Commissioner.***CreditsHost: David D. StewartExecutive Producers: Jeanne Rauch-Zender, Paige JonesProducers: Jordan Parrish, Peyton RhodesAudio Engineers: Jordan Parrish, Peyton Rhodes****This episode is sponsored by Crux. For more information, visit cruxclimate.com/contact. This episode is sponsored by Avalara. For more information, visit avalara.com. This episode is sponsored by the University of California Irvine School of Law Graduate Tax Program. For more information, visit law.uci.edu/gradtax. Nominate someone for the Tax Analysts Award of Distinction in U.S. Federal Taxation! For more information, visit awards.taxanalysts.org.

Philip Hwang, national chair of the Taxpayer Advocacy Panel, discusses the issues the IRS and return preparers could face this filing season following the passage of the One Big Beautiful Bill Act. For related tax news, read the following in Tax Notes:IRS Prepared to Meet Service, Collection Goals, Bisignano SaysProposed IRS Funding Cut Draws Concern From Tax WatchersIRS Sets Filing Season Start Date Amid Lofty Refund Expectations***CreditsHost: David D. StewartExecutive Producers: Jeanne Rauch-Zender, Paige JonesProducers: Jordan Parrish, Peyton RhodesAudio Engineers: Jordan Parrish, Peyton Rhodes****This episode is sponsored by Crux. For more information, visit cruxclimate.com/contact. This episode is sponsored by Avalara. For more information, visit avalara.com. This episode is sponsored by the University of California Irvine School of Law Graduate Tax Program. For more information, visit law.uci.edu/gradtax. Nominate someone for the Tax Analysts Award of Distinction in U.S. Federal Taxation! For more information, visit awards.taxanalysts.org.

Jaye Calhoun of Kean Miller discusses key tax issues that states will likely address in 2026, including One Big Beautiful Bill Act provisions and the adoption of artificial intelligence tools. For related tax news, read the following in Tax Notes:Iowa DOR Issues Withholding Guidance on OBBBA Tax DeductionsU.S. Chamber Backs Florida Bid to Challenge California Apportionment RuleStates to Face Budget, Tax Policy Questions in 2026 Conformity Debate***CreditsHost: David D. StewartExecutive Producers: Jeanne Rauch-Zender, Paige JonesProducers: Jordan Parrish, Peyton RhodesAudio Engineers: Jordan Parrish, Peyton Rhodes****This episode is sponsored by Crux. For more information, visit cruxclimate.com/contact. This episode is sponsored by Avalara. For more information, visit avalara.com. This episode is sponsored by the University of California Irvine School of Law Graduate Tax Program. For more information, visit law.uci.edu/gradtax. Nominate someone for the Tax Analysts Award of Distinction in U.S. Federal Taxation! For more information, visit awards.taxanalysts.org.