What’s 🔥 in Enterprise IT/VC #497

In the Trenches with 50 Midwest CIOs: Agents, Context, Costs, and Real Enterprise AI.

May 09, 2026

I spent a couple of days in Chicago this week with 50 CIOs, CTOs, and Heads of AI, from household-name enterprises across regulated, legacy-heavy industries. These weren’t AI tourists. They were the people responsible for making this stuff work.

And the biggest takeaway was simple: despite everything we read online, enterprise agents are still very, very early and there is still so much to build!

Ed Sim@edsimSitting in Chicago with 50 CIOs and AI leaders at large Midwest enterprise household names and when asked who feels like they are using agents at scale, no one raised their hand. Still so so early despite what you read on X. 1:24 PM · May 7, 2026 · 1.1K Views3 Replies · 1 Repost · 12 Likes

When the room was asked who felt they had agents operating at scale, no one raised a hand. In a smaller agentic workflow breakout, only 5 of 25 said they had agents in production at all. The concerns were consistent: security everywhere, not just in the CISO office; ROI that is still hard to measure; legacy systems that must be modernized before AI can truly scale; unclear governance and ownership models; and rising questions around vendor claims, data readiness, build-vs-buy decisions, and agent lifecycle management. The demand is real, the executive urgency is real, but the production operating model for enterprise agents is still being invented in real time.

Another huge issue: many enterprises did not even know where to start because the underlying work is not well documented. Before you can deploy agents, you need to understand the actual workflows, handoffs, approvals, exceptions, and systems of record. And once those processes are mapped, the answer should not be to blindly automate them. Many of these workflows need to be rethought, simplified, or reengineered first. That creates a big opportunity for tools that help enterprises discover how work really gets done, decide what should change, and only then bring AI and agents into the flow.

Even once you've mapped the work, the next problem hits fast: cost. One leader described a pattern where a tiny sliver of users was burning the majority of tokens. That's how AI finops becomes a real discipline overnight - budgeting, routing, usage controls, the works.

Uber is well ahead of most enterprises here, and even Uber is feeling it. As the company has gotten more agent-pilled, the token bill has gotten ugly.

Bearly AI@bearlyaiUber’s CTO recently said the company had already burnt through its entire token budget for 2026. In a recent interview, Uber CEO Dara Khosrowshahi explained how internally they switch between AI models to try and control costs: create V1s with frontiers, then switch to cheaper 4:52 PM · May 4, 2026 · 116K Views14 Replies · 44 Reposts · 372 Likes

If I combine Uber’s comments with what I heard from the more mature organizations at the summit, it feels pretty clear that AI cost management is going to become a Tier 1 enterprise pain point over the next 12 months.

For many enterprises, it will always start with the “easy” button to get their workers agent pilled using Claude or Codex. Eventually, the likely answer is not “use the best model for everything.” SOTA models for the highest-value work, then route other tasks to cheaper models, smaller models, older generations, or more deterministic systems depending on the use case and required quality.

This is also why companies like Atlassian are talking so much about Rovo, context, and owning that layer. Michael Cannon-Brookes’ point from the earnings call was exactly this: if you understand the work, the people, the permissions, the tickets, the docs, and the workflows, you can make AI more useful and more cost-efficient. The more organized and business-aware the context, the less waste you feed into the model, the better the outcome, and the more manageable the token bill.

Here’s Boris Cherny, Head of Claude Code, on why context matters in the messy enterprise and why ServiceNow’s pitch is landing: organize the dependencies, data, and workflows in one platform, reduce complexity, and feed models cleaner context. With 7T transactions and 100B workflows, that can mean better outcomes and lower token costs.

The Claude Portfolio@theaiportfoliosBoris Cherny, Head of Claude Code, on the importance of ServiceNow $NOW 5:01 PM · May 5, 2026 · 23.5K Views91 Replies · 16 Reposts · 226 Likes Ed Sim@edsimInsane context inside the messy enterprise. Assets tied to compliance processes. Approval chains. Vendor history. Business rules. $NOW has trained on: 95B+ annual workflows 7T+ transactions Frontier labs have the models. They don’t natively have the enterprise context graph.Ed Sim @edsimWhether or not you believe ServiceNow can reach $30B in revenue, with 30%+ from AI products, the bigger point is clear: Enterprise workflow automation won’t be “just GenAI.” It will require deterministic systems, probabilistic reasoning, human-in-the-loop decisions, and fully11:37 AM · May 6, 2026 · 1.18K Views1 Repost · 5 Likes

Finally, there was real frustration with Microsoft and other large vendors. As pricing shifts toward consumption, enterprises feel less predictability and more walled-garden pressure. No one wants to rip out SAP overnight, but the cost of accessing and moving their own data is starting to grate. Increasingly, many just want to treat these ERPs as headless systems of record. The opportunity, once again, for startups is going to be huge in the coming years.

We are still early on enterprise agents. But the next race is already clear.

For most non-tech enterprises, the winners won’t be the ones with the best model. They’ll be the ones that know where the work lives: the workflows, the context, the governance, the cost controls.

The frontier labs have the intelligence. They don’t have the enterprise.

That’s the gap. And it’s where the next decade of value gets built.

As always, 🙏🏼 for reading and please share with your friends and colleagues!

Scaling Startups

so agree!

Alex Callinicos @alexcallinicos.bsky.social@alex_callinicosInteresting from Gillian Tett 7:33 AM · May 8, 2026 · 370K Views103 Replies · 961 Reposts · 6.89K Likes

not your usual AI layoff email from Brian at Coinbase with a focus on speed and startup mode - more importantly orgs have to rethink how work is done in an AI native world: “We’re rebuilding Coinbase as an intelligence, with humans around the edge” - max 5 layers, No pure managers (player-coaches only), AI-native pods + one-person teams

Brian Armstrong@brian_armstrongThis is an email I sent earlier today to all employees at Coinbase: Team, Today I’ve made the difficult decision to reduce the size of Coinbase by ~14%. I want to walk you through why we're doing this now, what it means for those affected, and how this positions us for the10:55 AM · May 5, 2026 · 153K Views439 Replies · 157 Reposts · 1.35K Likes

breakdown of YC’s latest class (h/t Robert Scoble) - lots of infra building for agents, not humans

no better time to start a company - the best technical talent has an abundance of capital to access…or they can join a frontier lab and get paid a ton and have zero direct reports 🤣

Chris Bakke@ChrisJBakke“You can still make $30M TC but you don’t have to manage a team of 3,600 people” is a pretty great value prop for a lot of public co CTOsHenry Shi @henrythe9thsSomething strange is happening in tech. CTOs of billion dollar companies are quitting to take IC roles at Anthropic. Workday CTO -> MTS (Mar 2026) You[.]com CTO -> MTS (Mar 2026) Instagram CTO -> MTS (Jan 2026) Box CTO -> MTS (Dec 2025) Super[.]com CTO -> MTS (July 2025) Adept6:54 PM · May 1, 2026 · 186K Views9 Replies · 35 Reposts · 1.76K Likes

great list of investors who move with speed…🙏🏻 to be included

boldstart ventures@BoldstartvcWe @Boldstartvc are built for speed. 48 hours to terms many times. Also well beyond classic enterprise. Long been investing in AI infrastructure, cybersecurity, chips, and physical AI including @GeneralistAI @ToposBio from inception/ideation Please reach out!Ksenia Moskalenko @kseniam0sSome VCs take 6 months to say no. Some of these have given term sheets in under 48 hours: - @CRV any partner can say yes without committee approval. 24 hours. - @HustleFundVC built the whole fund model around speed - @Boldstartvc enterprise seed, will move same week if they12:58 PM · May 4, 2026 · 917 Views1 Reply · 6 Likes

how not to get killed by the frontier labs

GTMnow@GTMnow_The Founder & GP of @Boldstartvc, @edsim, on how he underwrites AI companies in a market that can flip overnight: The pitch is strong. The team has passion. The product works. Then the partner meeting hits the real question: what happens next Tuesday when the frontier modelEd Sim @edsim30 years of venture investing and I've never seen a market move this fast with so much uncertainty which means huge opportunity. 🙏🏻 @HackItMax - we covered a ton of ground on some of my frameworks for investing + working with founders like the 5 P's and 3 CH's. Going to point2:52 PM · May 5, 2026 · 886 Views4 Reposts · 6 Likes

Enterprise Tech

great read on agents and harnesses and so agree with this point

Frontier closed models are far too expensive for the large majority of tasks the world needs to do. As teams start mapping costs to ROI, Open Model Harness Engineering will take off even more. It is almost always worth the investment to at least try to get a potential 20x+ cost reduction

Viv@Vtrivedy10Strong Opinions, Loosely Held on Agent + Harness Engineering: 1. You can outperform any default harness+model (including codex & claude code) on pretty much any Task by engineering the harness around it. Using the exact same model, curate prompts, tools, skills, hooks for that6:58 PM · May 6, 2026 · 23.5K Views24 Replies · 35 Reposts · 368 Likes