This article is sponsored by College Readiness Consulting!
Workday (NASDAQ: WDAY) Has a Midlife Crisis—Here’s How to Snap Out of It
Workday used to be the cool SaaS kid on the HR block—helping Fortune 500 giants ditch clunky Oracle setups and finally run payroll without crashing the server. But in 2024 and 2025, it’s been… quiet.
Too quiet.
While peers like Salesforce and ServiceNow are launching AI features every five minutes (some real, some pure vapor), Workday’s stock has stalled, growth is slowing, and investors are starting to wonder: is this just a boring, stable compounder—or is something actually wrong?
Spoiler: It’s a little of both–and its stock has been trading sideways over the last few months as proof.
Let’s walk through what Workday needs to do to get back on the offense—before Wall Street files a formal HR complaint.
1. Stop Confusing “Mission-Critical” With “Margin-Crushing”
Yes, Workday is sticky. Yes, HR and finance systems are hard to rip out. But mission-critical doesn’t mean you can coast—especially when customer acquisition costs are ballooning and the “land-and-expand” motion is starting to look more like “land-and-stand-there.”
Workday’s operating margins are finally moving in the right direction—but only after years of investors begging them to stop spending like a freshly funded startup.
Fix:
Run a real margin play. Workday should lean harder into automation, lower implementation costs with more standardized packages, and—this is crazy—maybe stop treating every new enterprise deployment like it’s a custom couture suit.
2. Build a Real AI Strategy—Not Just an Earnings Call Script
Every Workday earnings call now includes at least three mentions of “AI.” But let’s be honest: nobody knows what any of it does.
“We’re embedding generative AI across our platform” is great, but what does that mean for the HR director at a logistics company who still prints payroll spreadsheets?
While others are launching AI copilots, resume screening bots, and predictive compensation tools, Workday’s innovation cadence feels like it’s being reviewed by Legal… and then re-reviewed… and then forgotten.
Fix:
Launch something real. Automate headcount planning. Predict attrition risk. Generate job descriptions and DEI reports with a click. And whatever you do—don’t let SAP beat you to it.
3. Fix the Mid-Market Strategy
Workday has spent years chasing the Fortune 1000. And it shows—its sales cycle is slower than HR onboarding in a union shop. Meanwhile, the mid-market is growing, underserved, and ripe for the taking.
But right now? That space belongs to Paycor, BambooHR, Rippling, and Gusto. Workday is barely invited to the cookout.
Fix:
Launch a lighter version of the platform (Workday Lite™?). Offer quick-start templates. Partner with mid-sized consultants. You don’t need to babysit their org charts—just get in the building before someone else does.
4. Get Over Your Oracle Complex
Yes, Oracle is evil and bad for your core business. Yes, Larry Ellison is probably planning something and might just beat you. But you’re not the underdog anymore. Workday has its own sprawl, its own red tape, and its own moments of being “just as bad” as the legacy vendors it once sought to destroy.
If you don’t believe it, ask any HR team about their last Workday implementation timeline. Or try deleting a custom report. We’ll wait.
Fix:
Simplify. Workday should embrace the elegance and speed that once defined it—and ditch the Frankenstein-level customization bloat. You’re still better than Oracle, but the gap’s closing fast.
5. Turn the Partner Ecosystem Into an Actual Flywheel
Salesforce has its AppExchange. ServiceNow has a whole consulting army. Workday? It has “certified implementation partners” and… a few Slack groups?
The platform is too powerful to not have a vibrant ecosystem of add-ons, automations, and niche vertical solutions. Right now, that’s a wasted opportunity.
Fix:
Open the gates. Incentivize developers. Build a real marketplace. Let the community create verticalized solutions for healthcare, education, retail, and manufacturing—without waiting for Workday’s roadmap committee to approve every idea.
Final Thoughts: Workday’s Still a Tank—But It Needs a Turbo
This isn’t a broken company. It’s just… boring. Safe. Conservative. Reliable.
That’s fine if you’re a retirement fund. But in the world of cloud software? Investors want a little more sizzle.
Workday has the brand. It has the customer base. It has the recurring revenue. Now it needs urgency.
So take off the HR lanyard, put down the process checklist, and go build again.
DISCLAIMER: This analysis of the aforementioned stock security is in no way to be construed, understood, or seen as formal, professional, or any other form of investment advice. We are simply expressing our opinions regarding a publicly traded entity.
© 2025 MacroHint.com. All rights reserved.