Software Rationalization Playbook

Why Software Rationalization Breaks Down at Enterprise Scale

Software rationalization does not fail due to lack of intent or intelligence. It fails because of structural realities in large organisations: software data is spread across multiple, imperfect sources, no single tool ever confirms the full picture, software enters the estate faster than governance can react, and rationalization is treated as episodic, not operational.

Industry research indicates that SAM value is created through decision enablement, not theoretical inventory completeness. The mistake organisations make is waiting for a single perfect source of truth while hybrid infrastructures make tracking usage increasingly difficult.

Progressive SAM does not wait, it converges. This approach allows IT leadership to move from reactive reporting to enterprise decision leadership by building trusted data foundations in real-time.

What Makes LICENSEWARE Fundamentally Different

Many tools promise clarity after integration projects, while others promise speed by ignoring governance altogether. LICENSEWARE delivers answers in a day, from a foundation you’ll trust, enabling decisions you won’t regret in 12 months.

It achieves this by building trusted data quickly, not by pretending a perfect source exists. Our modular app ecosystem allows you to address specific vendor complexities, such as Oracle licensing or Microsoft estate rightsizing, without a monolithic rollout.

Phase 01

Build a Trusted Golden Record, Fast

No single discovery tool has the full truth. Trusted data emerges when multiple sources converge. LICENSEWARE ingests software data from existing discovery tools like SCCM, Intune, Jamf, CrowdStrike, and Lansweeper, as well as CSV exports, APIs, and the LICENSEWARE Collector.

The Software Inventory Manager (SIM) acts as the central intelligence hub, normalising names and enriching data continuously. This approach routinely delivers 95–99% estate visibility without waiting months for remediation.

SAM execution

  • Ingest all available sources immediately to identify quick wins.
  • Do not block progress on perfection; leverage convergence to establish trust.
  • Use the LICENSEWARE Collector for granular, cross-platform usage telemetry.
  • Enforce high data quality through automated GREG mapping.
Phase 02

Eliminate Software That Should Never Be There

The fastest rationalization wins are obvious. Using SIM combined with NEO Insights, Risk & Hygiene, SAM teams surface games, torrenting clients, and shadow communication platforms.

These tools introduce significant security exposure and audit blind spots. By producing a risk-ranked list within a day, SAM teams can frame findings in policy language, escalating directly to the CISO or IT operations for immediate enforcement.

Phase 03

Rationalize Functional Duplication, Not Vendor Count

Enterprise rationalization succeeds when reframed as “We have multiple tools doing the same job.”

SIM reveals functional categories with overlapping tools, install volumes by product, and free vs paid duplication. This allows SAM to engage Product Owners with clear recommendations, positioning rationalization as a strategy for standardisation and long-term sustainability.

Phase 04 & 05

Prioritise EOL and Monthly Governance

Not all End-of-Life software carries equal risk. NEO Insights prioritises EOL remediation based on business criticality and install count. This prevents “fixing everything at once” and focuses leadership on high-impact remediation.

Rationalization then becomes a monthly governance cadence. From the same golden record, SAM can confidently engage stakeholders: Procurement for renewal leverage and the CISO for attack surface reduction.

Traditional SAM
Progressive (LICENSEWARE)
Single source obsession
Multi-source convergence
Project-based cleanup
Continuous governance
Licence-centric
Decision-centric
Fragile trust
Compounding confidence

LICENSEWARE ensures your data trust compounds over time, ensuring rationalization does not decay and new sprawl is detected early.

THAT IS PROGRESSIVE SOFTWARE ASSET MANAGEMENT.

Shaun Ashbury

Shaun is an ITAM Community Champion. Dedicated to connecting the ITAM world together through shared knowledge and championing fellow ITAM professionals sharing knowledge to help others. Shaun is a Senior Consultant at Licenseware, helping customers reduce software spending. Shaun is also a podcaster at Off Menu IT [Alternative ITAM solutions] where he interviews start-ups, independent firms, and services who are not the typical go-to.