The Application Portfolio Optimisation Roadmap: A 90-Day Quick Start Plan

A practical 90-day action plan to kickstart your application portfolio optimisation journey. Week-by-week activities, milestones, and quick wins to demonstrate immediate value.

Why 90 Days?

The Right Timeframe for SMEs

Ninety days is long enough to complete a thorough assessment and deliver meaningful results, but short enough to maintain momentum and executive attention. This plan is designed for SMEs with 20-200 employees and 30-150 applications.

Expected Outcomes at Day 90:

Complete application portfolio inventory
10-20% reduction in software spending identified
Clear roadmap for ongoing optimisation
Governance framework established
At least 3-5 quick wins delivered

Month 1: Discovery and Assessment (Days 1-30)

Week 1: Project Setup and Data Collection

Day 1-2: Project Kickoff

[ ] Secure executive sponsor and mandate
[ ] Assign portfolio manager and team
[ ] Define project scope and goals
[ ] Set up project tracking (simple Kanban board)
[ ] Schedule stakeholder interviews

Day 3-5: Financial Data Collection

[ ] Export all software-related expenses (past 12 months)
[ ] Identify all credit card charges to software vendors
[ ] Collect all vendor invoices and contracts
[ ] List all purchase orders for software
[ ] Check departmental budgets for technology spending

Week 2: Application Discovery

Day 6-8: IT-Managed Applications

[ ] Export application list from IT management tools
[ ] Document SSO-connected applications
[ ] List all on-premises installed software
[ ] Catalogue infrastructure and hosting services
[ ] Document all custom-built applications

Day 9-10: Shadow IT Discovery

[ ] Survey department heads on tools their teams use
[ ] Send company-wide survey on application usage
[ ] Review network traffic for unknown SaaS services
[ ] Check browser bookmarks and saved passwords
[ ] Compile complete application inventory

Week 3: Assessment and Scoring

Day 11-13: Usage Analysis

[ ] Collect login data from all applications (past 90 days)
[ ] Identify licensed vs. active users for each application
[ ] Categorise users as heavy, regular, occasional, or inactive
[ ] Calculate feature utilisation where possible
[ ] Document workarounds and manual processes

Day 14-15: Cost Analysis

[ ] Calculate annual cost per application
[ ] Compute per-user cost for each application
[ ] Identify unused licenses (no login in 60+ days)
[ ] Map overlapping functionality across applications
[ ] Rank applications by cost and by cost-per-user

Week 4: Classification and Prioritisation

Day 16-18: Business Value and Technical Health Scoring

[ ] Score each application on business value (1-5)
[ ] Score each application on technical health (1-5)
[ ] Apply TIME framework classification
[ ] Identify high-risk applications (vendor, security, technical)
[ ] Map applications to business processes

Day 19-20: Assessment Report

[ ] Compile findings into portfolio assessment report
[ ] Identify top 10 optimisation opportunities
[ ] Calculate potential savings from quick wins
[ ] Present findings to executive sponsor
[ ] Get approval for Month 2 action plan

Month 1 Milestone: Complete portfolio inventory with scores and classifications for all applications.

Month 2: Quick Wins and Strategy (Days 31-60)

Week 5: License Cleanup

Day 21-23: Remove Unused Licenses

[ ] Remove licenses for users who haven't logged in for 60+ days
[ ] Downgrade over-provisioned license tiers
[ ] Consolidate individual subscriptions to team plans
[ ] Cancel duplicate subscriptions across departments
[ ] Switch monthly billing to annual where beneficial

Day 24-25: Track Savings

[ ] Document each change and associated cost reduction
[ ] Update portfolio inventory with revised license counts
[ ] Report quick-win savings to executive sponsor
[ ] Communicate changes to affected teams

Week 6: Consolidation Planning

Day 26-28: Identify Consolidation Targets

[ ] Map all applications with overlapping functionality
[ ] Evaluate which platforms can replace multiple point solutions
[ ] Assess migration complexity for each consolidation
[ ] Estimate costs and savings for top 3 consolidations
[ ] Build business cases with 3-year projections

Day 29-30: Retirement Planning

[ ] List all applications classified as "Eliminate"
[ ] Create retirement timeline for each
[ ] Identify data preservation requirements
[ ] Communicate retirement plans to application owners
[ ] Begin decommissioning lowest-risk retirements

Week 7: Integration Assessment

Day 31-33: Integration Health Check

[ ] Map all existing integrations between applications
[ ] Identify manual data transfer points
[ ] Assess integration reliability and error rates
[ ] Identify priority integrations that would eliminate manual work
[ ] Evaluate integration platform options

Day 34-35: Vendor Management

[ ] Review all contracts renewing in the next 90 days
[ ] Prepare negotiation briefs for top 5 vendor relationships
[ ] Research competitor pricing for negotiation leverage
[ ] Schedule renewal review meetings
[ ] Identify vendor consolidation opportunities

Week 8: Optimisation Roadmap

Day 36-38: 12-Month Roadmap Development

[ ] Prioritise all optimisation actions by impact and effort
[ ] Sequence actions to manage change effectively
[ ] Estimate resource requirements for each initiative
[ ] Set quarterly milestones and KPIs
[ ] Create governance framework for ongoing management

Day 39-40: Stakeholder Alignment

[ ] Present roadmap to executive team
[ ] Get budget approval for next quarter initiatives
[ ] Assign owners to each roadmap initiative
[ ] Communicate plan to the broader organisation
[ ] Set up tracking and reporting mechanisms

Month 2 Milestone: Quick wins delivered (₹1-5 lakh savings identified), 12-month optimisation roadmap approved.

Month 3: Execution and Governance (Days 61-90)

Week 9-10: Execute Priority Actions

Day 41-50: First Consolidation Project

[ ] Begin migrating users from redundant tool to preferred platform
[ ] Execute first application retirement (data archived, access removed)
[ ] Implement top-priority integration to eliminate manual work
[ ] Negotiate renewals using competitive pricing data
[ ] Train users on consolidated tools

Week 11: Governance Implementation

Day 51-55: Establish Governance

[ ] Publish application procurement policy
[ ] Create approved application catalogue
[ ] Set up monthly portfolio review meeting
[ ] Implement renewal tracking (90-day advance notice)
[ ] Assign application owners for all portfolio applications

Week 12: Results and Sustained Operations

Day 56-58: Measure and Report

[ ] Calculate total savings from 90-day initiative
[ ] Report on portfolio health metric improvements
[ ] Document lessons learned
[ ] Update TIME classifications based on actions taken
[ ] Create portfolio health dashboard

Day 59-60: Transition to Ongoing Management

[ ] Confirm governance roles and schedules
[ ] Set up automated monitoring and alerting
[ ] Schedule quarterly portfolio reviews
[ ] Plan next quarter's optimisation initiatives
[ ] Celebrate wins and recognise the team

Month 3 Milestone: Governance established, first projects completed, savings realised, and sustained management practice in place.

Expected Results at Day 90

Quantitative Outcomes

Applications discovered: 100% of portfolio visible
License savings: 10-20% reduction in software spending
Applications retired: 3-5 redundant or unused applications
Integrations improved: 2-3 manual processes automated
Better contracts: 1-2 vendors renegotiated

Qualitative Outcomes

Clear understanding of portfolio composition and health
Data-driven decision making for technology investments
Governance framework preventing future sprawl
Executive visibility into IT spending
Foundation laid for digital transformation initiatives

Critical Success Factors

What Makes This Work

Executive sponsorship: Someone senior visibly supports the initiative
Cross-functional participation: Business and IT collaborate
Data-driven decisions: Facts, not opinions, drive actions
Quick wins first: Early savings build momentum and credibility
Sustained governance: Don't let the optimised portfolio drift back

Common Pitfalls to Avoid

Analysis paralysis: Don't aim for perfect data before acting
Ignoring change management: People resist losing familiar tools
Under-communicating: Tell people what's changing and why
Declaring victory too early: Governance is what sustains results
Going it alone: Get help from specialists if needed

The 90-day mark is not the end—it's the beginning of sustainable portfolio management. Use the foundation you've built to continuously optimise, govern, and evolve your application portfolio in alignment with your business strategy.