What Makes Enterprise Software Sticky? (SAP, Workday, Atlassian)

Why I’m Looking at This

I kept hearing “enterprise software” thrown around like it’s a separate universe from consumer apps. At first, I thought: isn’t it all just databases and forms? But then I noticed companies spend years migrating from one platform to another, and entire consulting firms exist just to help with implementations. That seemed like a signal that something deeper was going on.

What These Platforms Do

SAP: Handles finance, supply chain, and logistics. It’s basically a giant system for tracking money, inventory, and orders across different countries and regulations.

Workday: Manages employee data and financial reporting. The interesting part is how it ties worker records (who reports to whom, what they’re paid) to ledger accounts (where does their salary show up in the budget?).

Atlassian (Jira/Confluence): Tracks work. Issues, projects, documentation. developers use it to manage bugs, features, and releases.

Why They’re Hard to Replace

At first glance, these look replaceable. But here’s what I’ve learned:

1. Data models are opinionated: SAP has a specific way of modeling a “purchase order” with approval steps, vendor relationships, and accounting codes. Switching platforms means remapping all of that.

2. Integrations lock you in: These systems connect to payroll providers, banks, identity systems, and dozens of internal tools. Each integration is a dependency.

3. Compliance and audits: If you’re a public company, you need audit trails. Who approved what, when, and why. These platforms bake that in. Rolling your own means rebuilding those controls.

4. Partner ecosystems: There are consulting firms that specialize in SAP implementations for specific industries (pharma, manufacturing). They bring templates and playbooks that speed up launches.

How Companies Actually Buy This Stuff

This blew my mind. It’s not like buying a saas tool for a side project. the process looks like:

1. Trigger: Something breaks (current system is too slow, can’t handle new regulations, etc.)
2. RFP (Request for Proposal): Company writes a doc listing requirements, vendors respond
3. Security review: IT and security teams vet the platform (data residency, encryption, access controls)
4. Pilot: Run a small test with one team or department
5. Commercial negotiation: Pricing is seat-based, or tied to number of employees, or transaction volume
6. Implementation: This is where it gets messy (see below)

Veto points: At any stage, someone can kill the deal—CIO says “doesn’t integrate with our identity provider,” CISO says “data residency rules violated,” CFO says “too expensive.”

What Actually Happens During Implementation

The word “implementation” makes it sound simple. Install the software, configure it, done. in reality:

• Data migration takes months. You’re mapping old employee records to the new system’s format, cleaning up duplicates, reconciling mismatches.
• Roles and permissions are political. Who can approve a purchase order? Who can see salary data? These aren’t just technical configs: they require buy-in from legal, HR, and finance.
• Integrations with payroll, banks, and other systems often break. You need automated tests and SLAs for each integration.
• Partners matter: A good consulting partner brings industry-specific templates (e.g., “here’s how pharma companies handle regulatory reporting in SAP”). A bad one just throws bodies at the problem.

Three Quick Snapshots

SAP: The Process Backbone

• Strength: End-to-end workflows (order → shipment → invoice → payment) with audit trails built in
• Risk: Complexity. Teams often customize too much and end up with “technical debt” that makes upgrades painful

Workday: The Unified Data Model

• Strength: Worker data and financial data live in one place, so reporting is consistent
• Risk: If you don’t enforce governance (who owns which reports?), you end up with “reporting sprawl”. Hundreds of reports no one maintains

Atlassian: The Work Graph

• Strength: Flexible. You can model issues, epics, and workflows however you want
• Risk: Without guardrails, teams proliferate custom fields and permissions until the system is a mess

What I’m Still Wondering

• When does it make sense to build vs. buy? If you’re a startup, can you just use simpler tools (Airtable, Notion) for longer? What’s the tipping point where you need “real” enterprise software?
• How do you measure success? Everyone says “time-to-value” but what does that actually mean? Fewer manual approvals? Faster month-end close?
• Why do migrations fail? I keep reading about companies spending $10M on an SAP implementation that never finishes. What goes wrong?
• AI’s role: Could AI speed up data mapping and reconciliation? Or does the “human owning the numbers” requirement mean automation only goes so far?

If you’ve worked on an enterprise software implementation (or survived one), I’d love to hear what actually happened.