Why Enterprise Software Keeps Failing the People Who Use It
In 2024, the average mid-sized business ran 187 different software systems across its operations—from
finance and HR to procurement, CRM, marketing, and IT.
On paper, it looks like digital transformation. In practice, it feels like death by a thousand logins.
Talk to the people on the ground, ops managers, finance analysts, support teams, dispatchers, project
leads and you hear a different story. They’re overwhelmed. They’re buried in clicks and workflows. They
know the work, but they can’t move the work.
They’re stuck in an endless loop of opening tabs, moving data, chasing approvals, reconciling reports, and
restarting automations that break when someone leaves the company or changes a field name.
The root cause? We’ve built software that’s brilliant at observing work—and terrible at actually doing it.
The Lie We’ve Been Sold
For decades, enterprise software has sold a singular dream: “If you can see the work, you can fix the work.”
We invested in dashboards, analytics platforms, BI layers, and alerts. We chased insights.
But what we got was visibility without velocity.
Today, software shows you what’s broken & leaves the fixing up to you.
That’s why work still lives in spreadsheets. It’s why every company has an operations hero who holds
everything together with email, intuition, and duct tape.
And it’s why most “digital transformations” quietly stall out after launch.
What Execution Failure Looks Like
Let me introduce you to Julia.
Julia runs operations for a $20M logistics company. She’s the kind of person every business leans on—
smart, resourceful, accountable. The one who never lets a ball drop. But behind the scenes, she’s
exhausted.
Every morning starts the same: four logins, ten tabs, a tangle of reports. She’s scanning delivery systems for
missed shipments, checking CRM entries for missing documents, comparing invoice statuses in accounting
software, and chasing down field teams via Slack to get answers.
She knows it shouldn’t be this way. That this work could be automated, orchestrated, even streamlined. She
asked IT once. They told her, “Put in a ticket. We’ll prioritize it next quarter.”
She laughed—half amused, half defeated.
It’s not the volume of tasks that’s wearing Julia down. It’s the constant feeling that she’s holding everything
together with brittle systems and sheer willpower. That if she takes a day off, things fall apart. That she’s the
glue. Unseen, irreplaceable, and slowly cracking.
Her team sees it too. The fatigue. The short replies. The creeping cynicism. She’s no longer brainstorming
ideas to improve processes… she’s just surviving them.
She’s good at her job. But she’s burned out. And she has no intention of staying another year.
Multiply her story across every department.
Meet Aisha, a finance lead at a manufacturing company with plants in three states. Her team spends the
first week of every month chasing down incomplete expense reports, manually reconciling vendor invoices
across two accounting systems, and massaging inconsistent data just to run a forecast. She once joked that
their quarterly report could be replaced by a single slide that says, “We’re not sure yet.”
Then there’s Marco, a field technician for a regional HVAC provider. Every day, he logs service reports into a
mobile app that doesn’t talk to inventory. Parts get restocked too late. Jobs get delayed. Customers call in
angry. Marco’s tools are modern, but they don’t talk to each other, and the frustration is boiling over.
Or take Dana, an HR manager at a 500-person retail chain. She spends her mornings helping team leads
navigate a jungle of disconnected tools for scheduling, compliance, onboarding, and performance reviews.
She’s lost count of how many promising hires fell through the cracks simply because nobody got notified in
time.
These are not edge cases. They’re the rule. The normal everyday operators in the millions of mid sized companies.
This is what execution failure looks like in the trenches of modern work., every mid-market company, every
country. That’s where our productivity is going to die.. She runs operations for a $20M logistics company.
Every morning, Julia logs into four different systems to figure out what failed overnight: deliveries missed,
drivers off route, documents not uploaded, invoices not closed. She consolidates that info into an Excel
sheet and emails it to three team leads.
She knows it’s a mess. But when she asked IT about automating it, she was told: “Put in a ticket. We’ll
prioritize it next quarter.”
Julia is the system glue. She’s talented, burned out, and has no intention of staying more than another year.
Multiply her story across every department, every mid-market company, every country. That’s where our
productivity is going to die.
Integration Was Supposed to Save Us
APIs were supposed to solve this. I once worked with a company that spent nine months and over $400,000
trying to integrate their customer service platform with their inventory and returns systems. On paper, the
integration was clean. In reality, it broke weekly.
One field name changed in the inventory database, and the entire return authorization flow collapsed.
Agents had to revert to manually copying order data from one screen to another—just like before the
project began. Except now, they also had to log bugs and attend weekly syncs with the outsourced
development team trying to patch the broken pipeline.
The VP who sponsored the project called it “our most expensive Ctrl+C, Ctrl+V solution.”. Then came RPA.
Then low-code. Then iPaaS. Then bots. Then AI.
But we replaced friction with fragility.
Every system integration added more overhead. Every automation relied on brittle logic. Every handoff
broke the moment something changed.
Salesforce reports that 76% of IT leaders say integration complexity is actively holding back progress.
Gartner estimates that through 2027, 75% of companies will still be managing app sprawl manually.
That’s not transformation. That’s tech debt with a fresh coat of paint.
What’s missing isn’t more data. Or better dashboards. Or faster alerts.
What’s missing is execution.
We need a layer that: Understands how work actually flows across systems – Connects intent to action,
without IT bottlenecks – Surfaces and resolves issues in real time – Gets better with every task completed
We need software that behaves like your most reliable ops manager: context-aware, quiet, relentless, and
fast.
Not another tool to learn. A system that gets the work done.
The Emotional Cost of Holding It All Together
This isn’t just a tech problem. It’s a human one.
The people filling the execution gap aren’t consultants or bots. They’re the Julias, Aishas, Marcos, and Danas
of the world. One employee recently told me, “I didn’t go into operations to babysit software. But that’s
what I do now—copying data between apps and apologizing for delays I didn’t cause.” Another said, “It’s
like I’m the human middleware holding this company together with my inbox.”. They’re employees
drowning in digital paperwork. And they’re quitting.
Employees aren’t leaving because the mission changed. They’re leaving because everything takes too long,
breaks too often, and gets patched with meetings.
We’re wasting human potential on system babysitting.
It’s costing us more than just time. It’s costing us retention, creativity, and growth.
What the Future Looks Like
The next generation of enterprise systems won’t just observe. They’ll execute.
They will: – Adapt to how people actually work – Automate the boring without breaking the business – Route
and resolve, not just notify and assign – Turn tribal knowledge into operational intelligence.
The companies that win will be the ones where the system doesn’t just know what needs to happen.
Take, for example, a mid-sized consumer goods company that recently implemented an adaptive execution
layer across their finance and supply chain tools. Before the shift, their AP team spent over 40 hours a week
reconciling invoices manually and chasing down approvals via email. After deploying an orchestrated
execution system, those tasks became automatic: invoices were matched and routed instantly, exceptions
were flagged with context, and approvers received daily digests instead of scattered notifications.
The result? Reconciliation time dropped by 70%. Approval cycles shrank from days to hours. And most
importantly, the finance team had time to focus on strategy instead of system babysitting.
It didn’t just improve productivity. It boosted morale. As one team member said, “For the first time, I feel
like I have a system that works with me, not one I have to fight.”
It gets it done.
If your team is still chasing approvals in Slack, copying data into spreadsheets, or rebooting workflows that
broke last week, you don’t have a transformation problem.
You have an execution gap.
Fix that, and the rest starts working like it should.