Diginomica co-founder + Enterprise Irregular who blogs/videocasts on the enterprise, w/ dash of bootstrappin' + media hacks. OK, I rant sometimes.
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Articles by Jon Reed
Enterprise hits and misses - AI outcomes are elusive, the human review tax is BS, and enterprises need an AI playbook
Main content diginomica picks - my top stories on diginomica this week: Connecting with the store - how Kroger has avoided the mistake of neglecting the offline asset aspect of the retail omni-channel equation - Stuart checks in on Kroger's omni-machinations, and finds them...
Oracle AI World 26 - how do we assess Oracle's AI progress versus customer realities? Podcast show review highlights
Main content One of the best ways to put a show to the test? Grab sneak into an empty room and hash out a podcast. At the close of the second day of Oracle AI World, I did just that - with Rebecca Wettemann of Valoir. (The Oracle AI World podcast review - with Rebecca Wettemann). No question, the biggest issue at enterprise events is the gap between the vendor's AI pursuits and the customers' readiness for adoption.
Oracle AI World 26 - if Fusion Claw changes enterprise work, does it change cost also? Oracle leaders reveal Fusion Claw economics
Oracle's Chris Leone and Mike Sicilia onstage I've held vendors' feet to the fire all year - for getting too far out in front of customers on their agentic AI visions, When the gap between customers and vendors is aspirational, that's a good thing. But when customers say, "I don't where to begin," then that's not so wonderful. How did Oracle fare on day one of AI World 2026? Well, there's a pretty big plot twist.
Enterprise hits and misses - agentic automation, or building things that matter? The hackening has begun - is enterprise security ready?
Main content Lead story - When AI can build anything, these are the things you should ship – and how I'm fixing to blow an agentic gasket. Why? Because I think the automation storyline is overdone. Yeah, I said it: I don't think it's going to be as easy to automate deterministic systems with probabilistic technology as so many of my peers do, however much "context" we attempt to apply. 2. Routine work should have already been automated by (more affordable) rules-based automation.
Enterprise hits and misses - buyers need better AI contracts - but is that enough? AI bubble talks get real and yeah - events events events!
Main content Lead story - No silver bullet for AI contracts - what buyers need to do instead - We are in dire need of better data on AI contract negotiations. During this madcap bonkers AI carnival event cycle, there's no question that customers have AI pricing and ROI high on their burning questions list. And: if you're a customer, you're not locking any of that in without better AI contracts - and savvier vendor negotiations.
Workday Rising - customers press customers on AI adoption and ROI, and get answers
Workday Rising '26 customer panel In my last post, I shared my dives into the four hottest AI topics: context, guardrails, pricing, and the skirmish for enterprise UX control (the "headless" developments). But what do Workday customers think on the ground? My customer interviews have been instructive - but nothing beats customers asking other customers for their AI adoption lessons.
Workday Rising - the hot topics of enterprise AI come to a head: it's about pricing, context, and (giving up) UX control
Workday Rising keynote - with Gerrit Kazmaier No sign of the SaaSpocalypse here. Workday entered the first full day of Workday Rising 2026 in uber-confident mode, talking up the re-invention of work and "The new Workday." What gives Workday that swagger? I believe underneath is a growing confidence that a multi-SaaS application and data footprint turns out to be an asset, not an impediment, to the "lawful" agents enterprises need.
Enterprise hits and misses - agentic harnesses need a (human) gut check, architectures need resilience, and event season rolls on
Main content (© Iconic Bestiary - Shutterstock) Lead story - Harness Unscripted - AI agents may be cool, but firms aren’t taking humans out of the loop I've spent more time on context than harnesses in this column, but they both matter. We could quibble over the definitions. Mine: "Context" - the umbrella term for how to get the right data into the LLM agent at the point of inference, so it can give responses and proposed actions that appear (mostly) smart and not tone deaf or missing vital info.
SAP Connect 2026 - SAP leadership responds to hot AI issues, and explains why "generic models" fall short
SAP's Christian Klein and Marielle Ehrmann SAP Sapphire is the splashiest SAP show - and few Sapphires were splashier than Orlando 2026. This year, SAP staked its claim to the so-called "autonomous enterprise" - with much exuberance. But here at the line-of-business event known as SAP Connect, things got real. The SAP Connect keynote was vastly superior to Sapphire's (hear our live review if you want).
The SAP Connect 2026 burning questions preview - how will human talent and AI agents fare in the end-to-end mix?
Main content Lara Albert - CMO of SAP SuccessFactors SAP Connect 2026 moves into high gear Tuesday, October 6. I'm on the ground at an analyst deep dive, and the burning questions are piling up. What should we be asking of SAP at this moment in time? Start here: How has SAP progressed in its "autonomous enterprise" framework since the SAP Sapphire keynotes in Orlando?
Enterprise hits and misses - AI, analytics are metrics - what are we missing? Enterprises confront AI Doomsday narratives, and event season rolls on
Main content Lead story - Does AI + analytics equal value? And can metrics lead us to outcomes? Barb tackled these issues in a two-parter. Start with: AI + analytics = value? (2/2) - why are we still having problems getting the data foundation right. (And does it really matter?). Problem statement?
Executive Intelligence podcast - Workday's Gerrit Kazmaier on facing down the SaaSpocalypse, and why Workday had to change before agentic AI took hold
Main content I believe the margin for success is enterprise AI projects is still narrow. All the more reason to learn from vendors getting traction with AI agents. But make no mistake, this is not the rogue agent approach that is dominating tech headlines with sensational scares. No, this is a different type of enterprise AI, propelled by what Workday calls "lawful" agents. But: not all customers are ready.
Enterprises hits and misses - are knowledge graphs the missing piece in AI context, and is agentic security broken, or just mismanaged?
Main content (© Black Salmon - Shutterstock) Lead story - Are knowledge graphs the agentic context differentiator? If we are to argue that 'agentic intelligence' is a real thing and not an oxymoron, then is anything more important to that intelligence than proper data context? I call this quest for proper context real-time organizational truth. In my stake in the ground on that topic, I emphasized context graphs as one key potential component of the required context layer.
Cloud ERP and AI disruptions - where are the real moats, and is a partner ecosystem one of them? Acumatica makes its case
On July 14, 2026, Acumatica acquired ISV partner Vertrax. Why does this matter? While most cloud ERP vendors talk about extensibility, Acumatica has a history of cultivating industry partners to the point of acquisition. A classic example? The 2020 acquisition of JAAS Systems, which built an entire manufacturing vertical on the Acumatica platform (I wrote about the run-up to this acquisition in 2019).
Enterprise hits and misses - AI needs more than ROI - it needs buyer trust. AI leadership needs a rethink, and Dreamforce is a wrap
Main content Lead story - Earning AI buyer trust - where do we go from here? My last piece sparked some discussion on the dilemmas of building AI trust. (What are the components of buyer trust for AI services? Time for an enterprise rethink!) My goal? Advance the discussion on buyer trust by compiling a list of trust requirements that would sufficiently challenge vendors - and customers.
What are the components of buyer trust for AI services? Time for an enterprise rethink!
Main content Folks, we have a maddening enterprise puzzle to solve. On the one hand, there is the vague blandness of "trust." As in: "enterprises buy from vendors they trust" - a totally useless, mind-numbing cliche. On the other, has trust ever been more important as a buying criteria than it is for AI software/services? Potent upside? Perhaps - but you're not getting that upside without embedding or fusing AI into mission-critical processes. And therein lies the risk.
Enterprise hits and misses - are AI agents employees, or not? Are enterprise harnesses ready, and are transfomer loops a security fail?
Main content Lead story - Are agents the equivalent of human employees - and should they be treated like one? It's a potent question - and my take may surprise you, at least a little bit. But first, let's have a look at Cath's two part series. We'll start with Treating AI agents like employees doesn't work - here's why! What is the argument in favor of treating AI agents as employees?
Enterprise hits and misses - bad data gives Marketing an AI hangover, Jensen Huang gives LinkedIn an AGI viral infusion, and fall events are here
Main content (Pixabay ) Lead story - How poor CRM data continues to plague Marketing's AI initiatives, but the board may not see it Hmmm... I'm detecting a boomerang theme here. AGI might be a fun topic for squandering an afternoon on LinkedIn for the weekend, but here in the real (enterprise) world, We're back to the dirty data -> crappy AI conundrum. Barb's on the case... Her focal point?
Time to get real about outcome-based pricing - can Genpact change the AI risk-reward equation for customers?
As I type, the enterprise software market is grappling with the most potent pricing/value confrontation it has faced. The instigator, of course, is agentic AI - a technology that brings eye-opening use cases, but not at what you'd call bargain-basement pricing. User seat licensing looks inadequate for what lies ahead. So do we shift into the promised land of outcome-based pricing, where customers pay based on results, not on market dictates?
Enterprise hits and misses - Salesforce and Workday defuse the SaaSpocalypse, tokenomics is a turning point, and prompt injections are a drag
Main content Lead story - Tokenomics - where are we now? Another day, another one million AI token(s). But what are we learning? The diginomica tokenomics megaseries rolls on. Start with Stuart's Tokenomics - "It was never about tokenmaxxing," insists Snowflake CEO Sridhar Ramaswamy.
How John Boos & Co. escaped the ERP customization trap, and built a 'perpetual platform' instead - an SAP cloud ERP story
(Maple Butcher Block from John Boos & Co.) ERP business cases have never been a cakewalk. Now, it's pressure cooker time. Consider these market conditions - and so many shiny new tech toys to choose from. You're not talking your CEO/board into an ERP migration on the back of a napkin. But there are indeed modern - and compelling - ERP business cases (analyst Josh Greenbaum and I have even developed a workshop format to flesh them out... See: Can LLMs spark team collaboration?
Enterprise hits and misses - agents need meaning, not just data. Anthropic grapples with model pricing, and retailers get an economic gut check.
Main content Lead story - Meaning, meet action! Why context engineering needs context We said "no good AI without data quality" - we were wrong (kind of). We thought "you need to serve up the right context for thx LLM" - wrong again, kind of. The most effective type of enterprise AI is about context, but the right context architecture is no small feat. And: even the right context doesn't necessarily lead to the right outcome, despite what some over-excited vendors may imply.
Executive Intelligence - can we build an agentic system of work? Oracle's Chris Leone on why enterprise AI can (and should) be different
Main content When I met Chris Leone at Oracle AI World New York City, he had some provocative things to say about the flaws in the AI market. My only regret was not getting him on a podcast then. But this summer, the timing worked. Our podcast coincides with a notable shift in the enterprise AI market: from 'intelligent automation' to building new agentic applications. Cue Oracle's July news on AI-native agent building.
How Essity transformed their B2B e-commerce platform on a global scale - an SAP Commerce Cloud story
Essity's Kiet Nhu and Daniele Tedesco Let's say you are a global consumer products brand - and you see big opportunities in transforming B2B e-commerce, while adding B2C channels. Ah, but there's a catch. You're already knee-deep in a global, ERP-driven transformation - in this case, SAP S/4HANA. And: you've learned the hard way that there are big downsides to a local approach to CX. You need a global CX template that makes new experiences viable across regions. But how do you get buy-in?
Enterprise hits and misses - tokenomics isn't going away, and neither is human talent. Bring on the expertise-as-commodity debate!
Main content Lead story - Tokenomics field lessons - where are we now? Tokenomics rolls on because, well, tokenomics rolls on. But let's see what we can learn from bruising AI pricing lessons, shall we? Start with Tokenomics - how Moody's AI fiscal discipline is setting its clients a needed exemplar. As Stuart notes, Moody's has a couple things going for them: a strong proprietary data edge, and token costs discipline.
Zero trust and breach containment in an agentic world - Zscaler CEO Jay Chaudhry on the new stakes of threat defense
Main content (Pixabay) As AI security drama hijacks enterprise news cycles with unsettling regularity, I keep coming back to my conversation with Zscaler. Billed as an "AI security platform built on zero trust," Zscaler is the perfect foil for everything that is preoccupies me with AI security: Will AI ultimately help defenders as much as attackers? (Even with the concerning Hugging Face attack from an OpenAI agent run amok, Hugging Face's defense included a Chinese AI model).
Enterprise hits and misses - OpenAI's agent hacks Hugging Face: enterprise takeaways and mythbusting. Plus: NVIDIA, Meta and MIcrosoft back open weight models
(© Pavel Danilyuk - Canva.com) Lead story - How can organizations best measure the environmental impact of AI across their entire value chain? The environmental impact of AI is one of the most important lingering storylines. It's not a simple issue to wrap heads around - especially when you consider that it's really the generative and agentic AI scaling, inferencing and looping that is driving the exponential energy consumption (and data center buildouts).
Deductions for an investment with and without LLC?
I am converting my primary residence to an investment property and understand the benefits of putting it in an LLC from an asset protection standpoint. I do already have a large umbrella policy. I'm interested in understanding how investor DEDUCTIONS may be handled differently on my tax return with and without an LLC? I believe I can deduct Mortgage interest, taxes, HOA fees, maintenance etc. plus depreciation, (which I don't have a handle on yet).
How Aeropuertos Argentina launched their Snow Agent for airport operations - an SAP AI story
Main content Gustavo Sabato, CIO Aeropuertos In my missive on real-time organizational truth, I argued that enterprise software vendors should apply more data imagination to AI use cases. And: AI agents can't be effectively intelligent without relevant real-time context - wherever that context might live.
Enterprise hits and misses - CIOs respond to the looming EU AI Act, while enterprises break away from frontier model addiction - but there are caveats
Main content Lead story - The EU AI Act needs more CIO attention - research from the diginomica network The European Union is a convergence of AI tensions, where the regulation-versus-innovation debate comes to a head - and the issue of data/AI sovereignty is right in the middle of it. Recently, Mark Chillingworth shared new feedback on the EU AI Act, via our diginomica network of CIOs and enterprise leaders. Why now?
Enterprise hits and misses - fun times with GEO and AEO, brands bring AI in-house, and the (expensive) problem of agentic loops
Main content Lead story - GEO or AEO - where do brands go from here? Reaching buyers matters - always has, always will. But increasingly, we need to reach the buyers and the bots, or reach the bots to reach some of the buyers, etc. Sound fun? Barb has the story in Generative Engine Optimization isn't the new SEO. Here's what brands need to do instead... And it's a good one. First off, re: GEO or AEO, can we just pick a term and be done with it?
Workday Elevate - what kind of AI do you want? Customers share AI success tactics - and how employees bought in
Workday Elevate customer talk with Pfizer I stirred a few pots with my 'context isn't enough' post. I wanted to push vendors (and I mean all vendors) to take context further - into real-time organizational truth. I also urged enterprises to rethink AI success, with some new proof points in mind: Studies have shown that smaller models can reduce LLM operating costs by as much as 90 percent.
Enterprise hits and misses - harness engineering takes over enterprise AI, and tokenomics is in full swing
Main content (Jehyun Sung on Unsplash) Lead story - In enterprise AI, the agent harness you choose matters more than the model Last week, I addressed reader pushback on my real-time organizational truth missive. I also unfurled something of a call to action: Studies have shown that smaller models can reduce LLM operating costs by as much as 90 percent.
Mind the maintenance gap! Christian Pedersen of IFS on how redefining innovation can change industries - and reduce energy consumption
Main content (Christian Pedersen IFS) Too many vendors have put the sustainability focus aside - to their detriment (and to their customers'). Let's be fair: it isn't easy to reconcile the AI imperative with responsible energy consumption. But that topic deserves an airing, not silence. I'm dismayed that ESG topics are viewed as toxic politics.
Enterprise hits and misses - AI context and real-time truth gets a debate, Ford rehires humans, and buyers weigh AI reults to date
Main content Lead story - AI context and real-time organizational truth - hot topics and bones of contention My AI research breakdown was intended to provoke a response, and it did: Why context isn't enough - AI agents need real-time organizational truth. Most of the pushback was of the best kind: the type that makes us (hopefully) smarter and better. What was I after?
Why context isn't enough - AI agents need real-time organizational truth
Main content Enterprise AI is a confounding place to be right now. The frontier model economy brings the unwelcome era of tokenomics, as the diminishing returns of LLM scale loom. Meanwhile, poorly implemented "AI First" mandates from Meta (and so many others) threaten a dystopian workplace. But the markets aren't all-knowing.
Enterprise hits and misses - customers respond to AI tokenomics, and vendors are on notice. Industry analysts get re-invented, and "data primacy" is a thing
Main content Lead story - tokenomics roundup number two - how are customers responding? Last week, I issued a roundup/analysis of tokenomics, and how vendors are rethinking AI pricing. But the story's not over, and Stuart's hits keep on coming. But this time, we have some new angles - including end user perspectives. Start with Stuart's Tokenomics - shift happens! Tech, lies, and FinOps at Prudential.
Where does Analyst Relations get stuck? In legacy events. Here's what enterprise analysts love (and hate) - and how the industry needs to change
Main content Is Analyst Relations disrupted by AI? Well, if you take your cue from analyst firm stock prices, reorgs and layoffs, then obviously yes. But I'd twist that argument: AI added a big jolt to an analyst model that's needed a big ol' jolt for a while. But now that we have a definite nudge towards cliff, what do we do about it? In 2024, I made the case for what I called next-gen analyst relations. The impact of generative AI on research - for better and for worse - hadn't really hit yet.
Enterprise hits and misses - vendors respond to tokenomics, but how well? US versus Anthropic ratchets up the AI regulation debate
Main content (Puppy riding on a unicorn © Michael Windser - LinkedIn) Lead story - Tokenomics and enterprise software - how are vendors responding to AI spend anxiety? At their best, enterprise vendors should be able to shield customers from (some of) their token pricing woes, but the term "at their best" definitely applies. There are pitfalls-a-plenty, both in getting AI pricing right, and talking about it effectively. So let's see what vendors have to say, shall we?
Executive Intelligence podcast - manufacturing is at the AI turning point, with Debbie Baldwin of Acumatica
Manufacturers have a different labor tension than we see elsewhere in AI. Most manufacturers need all the automation - and human talent - they can get. But to understand this AI moment in manufacturing, we need a deeper context. For that, I turned to Debbie Baldwin, Director of Product Management, Acumatica Manufacturing. We'll send you our top articles (and no marketing spam), no more than once a week.
Salesforce Connections 2026 - is Slack becoming Salesforce's best weapon in the pursuit of agentic UX?
Brandon Metcalf, CEO & Founder, Asymbl When Salesforce acquired Slack for $27.7 billion in July 2021, I heard plenty of consternation in the analyst back channel - from sticker shock to head scratching. But have circumstances changed? diginomica gets that feedback firsthand; guarding against excessive skepticism is part of the job. After all, we've heard similar AI talking points across many, many keynotes.
Enterprise hits and misses - can AI fix marketing, or is the treadmill just changing gears? Plus: Bain issues a data wake-up call on the ROI of AI
Main content Lead story - Where do marketers go from here, and can AI fix what ails them? Our Salesforce Connections coverage brought the future of marketers to a head - but there is more. Start with Barb's Marketing teams are being asked to do more with AI, so why aren't they getting the support from their leadership teams? Barb throws down the problem statement: If you’re a Marketer, then you hear every day that AI will make your job easier.
Salesforce Connections 2026 - SEO is out and GEO is here. But can commerce brands up their game?
Salesforce's Adam Levine presents on GEO I have a grouchy high bar for vendor value. This spring, I wanted enterprise software vendors to pull off two things at events: Present an energizing vision for customers to rally around, not a tokenmaxxing workplace dystopia. Show them how to get there, and where the rough edges are in that adventure. Proof points for where the AI results (and ROI) can be found doesn't hurt either.
Enterprise hits and misses - does the agentic enterprise have a friction problem, and is MCP ready for prime time?
Main content Lead story - If agentic AI truly makes every enterprise frictionless, what's left to compete on? Every now and then, I get a rare treat: a piece that requires me to rethink my premise - and re-evaluate my AI views. Last week, Derek du Preez accomplished that, in this must-read think piece on agentic AI friction. Start with the premise: how does AI change the frictionless enterprise, a diginomica methodology coined and developed by Phil Wainewright?
Enterprise hits and misses - Uber and Microsoft put the brakes on the productivity of AI tokenomics, while Google bites the data hand that feeds its AI search
Main content diginomica picks - my top stories on diginomica this week Delivering on fulfilment speeds and AI experience - a Walmart status report from CEO John Furner - Stuart has the Walmart AI and automation update: "Interesting to hear from Walmart’s management on the ongoing importance of tech investment. Target’s quarterly report earlier in the week came and went without a similar level of focus on show." Chris revisits the economics of drone tech in a new series...
SAP Sapphire 2026 - SAP CTO Philipp Herzig on SAP's API policy changes, and why "organizational memory" matters for agentic AI
(Dr. Philipp Herzig, CTO, SAP SE) Around April 23, I knew something was up: I started getting deluged with pings about SAP's API policy changes. I don't know about you, but when I hear about changes to fine print in data access, my bells always go off.
Enterprise hits and misses - AI results research reveal (the news is mixed), and is AI context a differentiator, or a Good Ship Lollipop for marketers?
Main content Lead story - New data from the diginomica network - Q1 2026 sees AI benefits despite a rough economy As we take the regular pulse of our diginomica CIO/CXO network, we can expect to see shifts in AI adoption and results. So where are we now? Mark Chillingworth has the reveal: There are early signs that investment in Artificial Intelligence (AI) is beginning to deliver measurable business value.
Enterprise hits and misses - AI results are elusive, but why? Tokenmaxxing is here, and AI (in)security is looming
Main content Lead story - AI results - the tension between expectations and reality mounts Up to this point, getting to AI results at scale is proving elusive. What's the issue - and what's holding us back? It's not a simple question - I personally believe there are compelling ways forward, but pitfalls are plentiful also.
Is the AI infrastructure layer now more valuable than software? Boomi CEO Steve Lucas raises the stakes with Boomi World on deck
Main content (Boomi CEO Steve Lucas talking shop) What are the scope of Boomi's agentic ambitions? We're about to find out at Boomi World 2026 in Chicago. Boomi was once described as an iPaaS vendor. Now, Boomi bills itself as a "data activation company." What is that?
Enterprise hits and misses - can brands re-invent with data and AI? MCP and AI security - offense or defense?
Main content Lead story - Brand re-invention stories - a closer look at Visa and Bed, Bath & Beyond Is there anything tougher for an enterprise than a brand re-invention, amidst the choppy waters of market disruption? That's certainly the case for Bed, Bath & Beyond, a beleagured brand that Stuart finally (almost) had to write off. But is that changing?
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