The Turn: Workday’s K-Shaped Future
Whether you buy that the talks to go private will go anywhere or not, Workday and other big SaaS companies have bigger issues to grapple with
I was at our county fair last week, eating a deep fried Oreo, and determining which of my daughter’s friends looked sicker after riding the Scrambler. It was a good time and, for a brief moment, I wasn’t thinking about SaaS.
Then I opened my email and saw a note from Siobhan Fagan, the editor of Reworked. She was one of a few people who sent me a note when rumors of Workday going private started circulating. She was doing a story and wanted a quote.
I voice-to-texted my answer over screaming people and the drone of carnival sounds, cleaned it up, and sent it her way. The next morning when it was published, I put together a quick post while I was picking up my travel trailer for one last camping trip of the summer. I typed it up on my phone and dropped in two logos in Canva so I had a visual and called it a day.
And that’s the story behind my most popular LinkedIn post of 2026. A post about Workday, written on a phone on a Friday. It’s a day I rarely post anything because I’ve never really had much luck. 125k+ impressions? Sure, why not.
Shows you what I know.
But I’m not posting about the mysteries of the LinkedIn algorithm. The fact is, I’ve been thinking about the finances of big SaaS ERPs like Workday, Oracle, and SAP for a long time and I even wrote about it last month (that was, no joke, one of my least popular posts of the year). I thought the underlying financial strain was an under-reported story that was worth examining from the lens of a buyer or customer.
At least I occasionally get some things right.
I’ve been on record that I’m not on the SaaS-pocalypse train. It just doesn’t make sense to me to build some of this stuff yourself. That doesn’t mean things are going to be easy for these big ERPs.
The suggestion of such a massive enterprise going private (and the accompanying stock bump) demonstrates the state of large SaaS ERPs better than the thousands of words written about it. While everyone seems to be skeptical of an update private equity playbook that doesn’t involve stripping off the parts that can be sold, loading it up with debt, and let some vulture take the scraps of the business when you’re done.
Thomas Otter takes a balanced position if you want to get into the nuts and bolts of why this one could (and should) be different. It’s a must read if you’re really into all that.
I don’t share the doomer position on going private that some of the people who have thoughtfully commented on my post do though. For one, even publicly-held companies are acting more like PEs than PEs. You just have to cross San Francisco Bay from Pleasanton to find Oracle, which is up to its eyeballs in debt and will be laying off thousands more to fund more AI.
Even though Treasury Secretary Scott Bessent said the overall economy isn’t K-shaped anymore, I believe companies like Workday, Oracle, and SAP are still in a real fight for which leg of the K they will be following. We’re still early but we have some clues about what doors are still open.
If I were immersed in the Workday ecosystem, I’d be less concerned about a take private deal that I don’t know the details of. I’d be much more worried about what happens if a deal doesn’t happen, Workday stays public, and they have to figure out how to win the right way. They can’t outspend Oracle, which is funding $40B of their infrastructure spend with debt and equity. While the market had been a little more forgiving with Oracle’s free spending ways earlier, their stock is now down 25% YTD.
A PE partner with a plan, resource alignment, and good leadership structure without the pressures of Wall Street gamesmanship sounds like as good of a bet as what we know about Workday’s public plans. Another wrinkle? We’re less than two months away from Workday Rising, which will put thousands of customers in front of the company where questions will be a lot harder to ignore.
As someone without a dog in the fight, it will be interesting to watch. The major ERP and HCM players are all hitting headwinds, though it is affecting them in different ways. What will this category look like in five years? I wish I could tell you (and make the appropriate stock purchases).
It might not beat a deep fried Oreo, but it’s an incredibly important story for every company you know the name of.
What else is happening this week?
AI’s Effect on Workplace Culture. In workplaces that rolled out AI, 25% of employees say the culture got worse against 24% who say it improved. Morgan Meinen and Megan Mulherin find the split is the manager: 33% versus 4% on whether work actually changed.
Is Your Culture Ready for AI? The Question Most Organisations Haven’t Asked. Mervyn Dinnen and Nick Holmes describe an AI-ready culture as one built on trust and purpose rather than an efficiency pitch. The bill for skipping that: 29% of employees say they actively undermine their employer’s AI strategy, 44% among Gen Z.
AI Hiring Tools Can Invent Their Own Bias, Research Finds. Princeton and Chicago gave four fictional groups identical odds and the models still sorted them into different jobs, per Jill Barth. Only an explicit diversity instruction fixed it.
What Happens When the Disruptor Becomes the Incumbent? Let’s Talk About Workday. Steve Smith‘s read on the Silver Lake rumor: investors don’t flash $50 billion at dying companies, they flash it at undervalued ones. It’s a good take on top of his usual good newsletter fodder.
Steal My Claude Setup. Laurie Ruettimann published the instructions she gives Claude so it edits like a partner instead of a ghostwriter. About 72 people marked up her last book, me included, and none of us got a watermark.
The Job Board Is Dead, Long Live the Job Board. Applications per posting doubled to 244 since 2022 while recruiting teams shrank by half. The fix Virginia Backaitis finds everyone arriving at is referrals: 7% of the pool, half the hires, older than job boards.
The Standard We’re Setting for AI Should Apply to Humans Too. Master Burnett takes Madeline Laurano‘s 41% who want full explainability from an AI interviewer and asks whether they could explain last week’s human decision. Only 17% wanted validation against job performance.
AI Governance: 1 Intro. Boards sign off on AI without anything close to the reporting they demand from accounting. John Sumser opens a new series with the evidence package that gap calls for, down to overrides and near misses.
Leaving Work on Time Is Not a Character Flaw. Madison Butler did the math on the extra 10 or 15 minutes at the end of the day: about 1,625 hours over 25 years. Her line is that your employer bought your labor, not your life.
What We’re Losing by Using AI for Everything. Mary Faulkner leaves the Zuckerberg demolition to The Verge and keeps the harder question for herself. There’s always a trade between efficiency and meaning, and somebody has to say out loud whether it’s worth taking.
Payscale Survey: Employers Plan 3.5% Raises for 2027. Inflation hit 4.2% this spring, so a 3.5% raise is a pay cut. David Manaster notes that a quarter of the 1,266 employers surveyed already believe weak raises cost them people, with another 22% unsure either way.
Extinction Has a Funny Way of Looking Like a Hiring Spree. SHRM’s CEO stood in front of humanoid robots and told a room of HR professionals their field faces extinction. Daniel Space calls that the language of a funeral describing a transformation.
Despite Massive AI Investment, Jobs in HR Are Booming. The Lightcast numbers behind that pushback are Josh Bersin‘s: HR postings up 6% over the last 24 months. He reads it as administrative HR work turning into consulting work, not disappearing.
The Edge of Now Episode 3: AI Can Find the Answer. Can Your Organization Still Think? Jess Von Bank and Jason Averbook want organizations to quit leading with prompt engineering. Their measure is whether you’re making better decisions, not whether you’re faster.
How Does Your Demographic Background Influence What AI Tells You? The study Steve Hunt surfaced found models tuning answers to what they’d worked out about the user, down to gender, income and location. Salary advice came back lower for women and for people of color.
The State of Workforce Compliance and Employee Trust. Compliance lands in the employee experience whether or not anyone planned it that way, which is the thread Steve Boese pulls with Experian’s employer services side.
AI Makes Intelligence Cheap. Judgment Becomes More Valuable. AI in recruiting is turning into infrastructure, closer to electricity than another app in the stack. Kevin Wheeler wants recruiters knowing when to question an output, not how the model was built.
AI-Generated Content Is Entering Its Google SEO Moment. LinkedIn now lets users flag low-value AI posts. Nicholas Biron sees that as the platforms starting to correct, the same way Google eventually came for SEO gaming.
When I Choose Work. At 17 the choice was a graduation dinner or a shift at American Eagle. The shift won, and twenty years on Kat Kibben concludes work never chose them back.
‘Did They Ghost You?’ Website Takes Aim at Employers Who Go Radio Silent on Candidates. More than 2,000 companies are listed, Apple and Microsoft among them, and at peak it was taking six reports a minute. The guy who built it told Paige McGlauflin that even a terrible final interview earns you a reply.
4 New Legal Questions Being Raised by Background and Identity Checks. Whether AI-assembled candidate profiles count as consumer reports under the FCRA is one of four fights Bob Quackenboss and Evangeline Paschal map out. Disparate impact is the one heading for the Supreme Court.
Average S&P 500 CEO Pay Surges 21% to Record High as Musk’s Mega-Deal Sets a New Standard. Average pay climbed 21% to $22.8 million with Musk excluded, against mean worker wages of $69,770. That’s 312 to 1, or 5,387 to 1 once you put Musk back in.
Google Insiders Warn Job Candidates About Its AI Hiring Filters. A team inside DeepMind told internal candidates to file a second form, because there’s a non-trivial chance the system screens them out by mistake. Jen Colletta on posting a rough road sign instead of filling the potholes.
Bank of America Won’t Let Employees Work Remotely 2 Days in a Row. Gabrielle Saulsbery reports the new rule closes the Friday-plus-Monday gap for staff who already owe three days in the office. Pick a lane: hybrid with one simple rule, or everyone in five days.
The Last Mile of Skills Transformation Is the Manager. Quarterly career conversations went from 8% in 2019 to 63% today in new Fuel50 research from Anne Fulton. Managers need that data in the conversation, not a quarter later.
What We Leave Behind. The 8:15 meeting exists because an executive who retired in 2021 had a commute, five years after he left. Robin Schooling writes about that kind of residue, and how little of it any knowledge management system will hold.
HC Insider: August 2026. Seat licenses made adoption the metric worth chasing. Tokens make it impact, which is the reframe Kyle Forrest leads with this month.
Sourcing Faster Without Losing the Human Part of Hiring. 93% of hiring managers say they’ve lost a strong candidate to a slow process. Dan Schawbel works that gap with Indeed and a solo recruiter, on a tool saving about seven hours a week.
How HR Can Own Workforce Transformation in the AI Era. Five podcast episodes condensed into one read by David Green. The neuroscience one has teeth: resistance is a protective response with six diagnosable causes.
Have a great rest of your week!