Musical accompaniment for this week’s newsletter.
There's a moment that keeps happening at conferences like Transform. Someone gets close enough to a microphone — or a hallway conversation — and says the thing everyone's been thinking but not saying. It happened at Transform, too. And somehow, this admission felt less like a confession and more like a sigh of relief. OK, so I’m not the only one who has no clue and is totally making all this s#!t up? That seemed to be the prevailing sentiment.
The official purpose of Transform is to build a more human future of work. Noble, a little aspirational, the right kind of mission statement for a room full of HR leaders. But, like everything else in our time, it’s more complicated than that. Everything feels fragmented, and the questions continue stacking up. Is AI embedded, or is it somewhere you go? What’s the strategy? What about governance? Where does AI even live inside an organization? Does it sit in IT? Product? The CHRO's office? Everyone's still negotiating that.
What doesn’t seem up for negotiation is that HR is getting stuck with figuring out how to make all this happen. In many organizations, there’s little in the way of strategy, governance, or any idea about the business problems AI needs to solve. Getting it all done? Just like when COVID hit, this transformation landed in HR's lap by default. When organizations don't have a clear answer for where AI lives, it ends up with the people team by process of elimination.
Congrats on your “seat at the table." Sorry about the mess we left in it.
There are contradictory signals everywhere. Vendors tell me that they are way out in front of their customers on AI. Release cycles that used to be every 24 months are now down to three. So, then why are some large enterprises insisting they are leaving their software vendors in the dust and are questioning their relevance?
There’s also a ripple of existential dread running underneath it all. I spoke to one HR leader who is in the midst of planning a major (like 40%) RIF in her org. She has to keep working closely with people she knows are on the list but who think they're safe. It used to be that layoffs came in waves around economic disruption. Now it’s just business as usual in the AI era.
For Work Tech vendors, don’t get too comfortable about the SaaSpocalypse being in the rearview mirror. After talking to investors who are a lot smarter than I am, it seems clear that whether AI can displace enterprise software vendors (and I still firmly believe it can’t) doesn’t really matter. The market's economic fundamentals are being recalibrated and repriced. The large strategics are feeling it first. Some are beginning to hit the brakes on M&A. Smaller players will begin to feel it acutely in the next 60 to 90 days. If you need to raise or exit, you may have a problem.
This is less a news report than a vibe check. If there was a bright spot for me personally, it was that the thing I love best about this industry is still humming along: The founders. The best ones in our industry are all trying to do the same thing – make work better and more human. That hasn’t changed. Whether it’s a young upstart with a great idea and killer execution or a multi-exit entrepreneur going at it one more time, Work Tech at its best is about the people, not the tech. I look forward to sharing some of these stories on the Work Tech Weekly podcast over the next few weeks.
We live in a challenging time. Nobody knows what they're doing. None of us have been here before. But a lot of us keep showing up and keep going after it. And that’s not nothing.
What else is going on this week?
At The Big Deel 2026, Deel announced GA of a fully native ATS — approved roles flow directly from Workforce Planning into recruiting, and accepted offers auto-populate into HRIS and onboarding without a handoff. This is the platform consolidation play in action: one less reason to maintain a standalone recruiting tool when payroll, compliance, and now hiring all live in the same system. (HR Tech Feed)
Origin raises $30 million in Series A+ funding. A CFO once told Origin CEO and co-founder Chris Bruce that he thought his company was spending ~$750 million annually on benefits — but had no way to verify it. That's the problem Origin is solving: AI that ingests fragmented global benefits data across languages, PDFs, and vendor portals into a single queryable layer. Benefits as the last untracked major budget line item is a real gap, and $50 million raised in under a year suggests the market agrees. (Finsmes)
Clasp raises $20 million Series B funding. Clasp's "ROTC for healthcare" model — commit to clinicians before graduation, repay loans over tenure instead of handing out sign-on bonuses that expire — is driving retention rates 2.5x higher than traditional hiring models. With federal loan caps tightening in July, the financial pressure on clinician candidates is about to intensify, which makes loan-linked hiring look less like a gimmick and more like a valuable perk. (Finsmes)
Allvia acquires HR Pals to expand its integrated workforce services platform. PE-backed Allvia — only formed in February — is already on acquisition two, picking up the LA-based HR outsourcing firm that's been on the Inc. 5000 four years running. When a platform company moves this fast in the HR services roll-up space, the bet is usually on scale and bundling before AI eats the category from below. (DHRMap)
Trayd raises $10 million Series A. Construction payroll is a genuinely brutal problem — union rules, prevailing wage laws, multi-state tax requirements, all colliding daily — and Trayd cut average processing time from 14 hours to 27 minutes. The fact that Y Combinator followed on (rare) and RXR came in as a strategic says the market is finally taking the trades seriously as a software vertical. (Finsmes)
Novaworks raises $8 million seed to build agentic workforce operating system. The real signal here isn't the dollar amount — it's that ServiceNow Ventures is both the platform and the check writer, which is about as de-risked a distribution bet as you'll find at seed stage. When the founders already sold their last HR AI company to ServiceNow, "AI-native HCM" stops sounding like a pitch and starts sounding like a plan. (DHRMap)
Companies aren't ripping out business software for AI — here's what they're doing instead. The "AI will replace your ERP" narrative is running into the same enterprise reality it always does: switching costs, compliance requirements, and the stubborn fact that the data is already in the old system. What's actually happening is augmentation — AI layered on top of Workday, Oracle, SAP — not replacement. Useful corrective for anyone who thought the incumbent vendors were toast. (Wall Street Journal)
AI is rewriting the old rules of Google Search and SEO. Google's AI Overviews are reshaping which content surfaces and which gets buried — with real implications for HR tech vendors, recruiting platforms, and anyone whose talent acquisition strategy includes organic search. The new SEO playbook is less about keywords and more about whether your content gets cited as a source by the AI layer on top. (Wall Street Journal)
OpenAI taps former Meta executive to lead ad push. OpenAI is building a consumer advertising business, and the hire — a seasoned Meta ad exec — makes the direction pretty unambiguous. For the Work Tech world, the downstream implication is that AI tools with free tiers are about to get a lot more interested in your job title, employer, and professional behavior data. (Wall Street Journal)
Workday launches agentic AI to transform enterprise execution systems. The Sana acquisition has officially been deployed: a unified AI interface with 300+ skills, consumption-based Flex Credits pricing, and connectors into Salesforce, ServiceNow, Outlook, and beyond. The shift from seat-based to outcome-based pricing is the quiet earthquake here. Workday is essentially betting its future on charging for work done, not software accessed. (DHRMap)
Oracle introduces Fusion agentic applications. Twenty-two new agentic apps dropped across finance, HR, supply chain, and CX — built natively inside Oracle Fusion Cloud so agents can actually execute decisions, not just whisper suggestions at a human. For the incumbents still bolting AI on top of legacy architectures, this is a reminder that native integration is starting to become a structural moat. (DHRMap)
Monday.com is bucking the norm with a big bet on HRBPs. While most companies are thinning out their HR Business Partner layers and leaning on AI to handle the transactional load, Monday.com is going the other direction — extending HRBP coverage down the org chart, betting that human context at scale is the thing AI can't replicate. (HR Executive)
Mark Zuckerberg is building an AI agent to help him be CEO. Because, yeah, that’s going to fix everything. Like that whole Metaverse thing. (Wall Street Journal)
Who will yell at the robot umpires? Jason Gay of The Wall Street Journal is the best sports columnist of our time. Period. Full stop. And, as with any great sports columnist, you are really writing about the game. You are writing about the culture. So, MLB is rolling out automated ball-strike technology that can overrule an umpire? It's a surprisingly good proxy for the same dynamic playing out in enterprise AI and robotics. (Wall Street Journal)
AI's $130 million lobbying blitz hands HR the real AI compliance burden. Tech giants spent roughly $130M lobbying for light-touch federal AI regulation in 2025 — and largely won, with the Trump administration pulling back Biden-era EEOC and DOL guidance. The catch: state-level AI employment laws are multiplying anyway, which means HR is now the de facto compliance layer in an increasingly fragmented legal landscape. (HR Executive)
Young grads face a grim job market. The unemployment rate for recent college grads ages 22–27 hit 5.6% — worst since the pandemic — while over 40% of employed grads are in jobs that don't require a degree. The main culprit isn't AI (yet); it's a "low hire, low fire" market where entry-level hiring dried up and nobody's churning out of jobs to make room. The AI displacement story is coming, but this is the less dramatic, more structural prequel. (New York Times)
Notes from UNLEASH: AI, trust, and the blur of differentiation. The floor at UNLEASH is getting harder to read — when everyone has "AI-powered" in the booth copy, the differentiators start to blur into background noise. The trust conversation is finally getting serious traction, though, which suggests buyers are moving past the demo phase and into the "what do I actually have to audit and govern" phase. (Aptitude Research)