MDI AI Strategy & Roadmap
PressW will partner with MDI and AWS Capital to deliver an adaptable and executable AI strategy for MDI that aligns with AWS Capital's investment thesis and exit strategy. This strategy will cover both MDI's product and platform portfolio and its internal operations, with the aim of socializing a compelling vision at the September 22–23 MDI customer conference.
The engagement will result in a prioritized AI opportunity backlog, a phased roadmap, and a conference-ready AI strategy presentation. Execution will occur in fast-paced feedback loops, enabling AWS Capital and MDI leadership to steer the process dynamically as new insights arise.
Guiding Principles & Success Markers
| Dimension | Success Looks Like (Qualitative) |
|---|---|
| Strategic Clarity | Leadership can articulate top AI opportunities and their rationale |
| Technical Feasibility | Clear, aligned solution patterns exist for each major opportunity |
| Organizational Readiness | Internal champions understand resourcing, data, and compliance needs |
| Value Realization Path | A lightweight measurement template is co-developed |
*Final KPIs and ROI frameworks will be developed only after discovery confirms opportunity size.
The Strategy: How We'll Prioritize
To ensure we focus on the most valuable initiatives, we'll employ a structured framework to map and prioritize all identified AI opportunities. This section explains our methodology for making strategic, data-driven decisions together.
Interactive Opportunity Matrix
This chart visualizes potential AI projects based on their strategic value and ease of implementation. Hover over each bubble to explore hypothetical opportunities and understand how our prioritization matrix works in practice. This tool helps us identify the "quick wins" and plan for more complex, high-impact initiatives.
The Scope: What We'll Cover
Our engagement is structured into two parallel workstreams covering both external products and internal processes, supported by foundational technical assessments. This section details the specific areas of focus within each track.
A
Track A: Product & Platform
Products & Sub-items
Automation & Augmentation Opportunity Briefs
Guided Quoting
AI-driven intelligent quoting system that automates price calculations, risk assessments, and policy recommendations while maintaining human oversight.
"Explain My Policy" Chatbot
Intelligent conversational agent that provides instant, accurate policy explanations and answers customer queries in natural language.
COI Document Agents
Automated Certificate of Insurance (COI) document processing, validation, and compliance monitoring using computer vision and NLP.
Claims & Policy Servicing Copilot
Real-time AI copilot for claims processing and policy servicing that enhances agent productivity and decision-making.
Underwriting Agents
AI-powered underwriting assistants that automate risk assessment, policy evaluation, and decision support for complex cases.
Additional Opportunities
Additional automation opportunities identified during discovery sessions across sales, marketing, and finance operations.
Formal Outputs
- Prioritization feasibility assessment
- Ranked backlog of opportunities
- Preliminary UX Concepts
- Technical architecture specifications
- Data pipeline integration blueprints
- Security and compliance frameworks
B
Track B: Internal Operations
Primary Focus Areas
- •System configuration
- •Conversion
- •Workflow analysis
- •Special projects
- •Ongoing management
- •Developer Productivity Assessment
- •Org Chart Recommendations
- •Site manager enablement & optimization
- •Online help chatbots
- •User Group enablement & optimization
- •Sales and Marketing organization Opportunities
- •Finance organization opportunities
Formal Outputs
- Automation/augmentation Opportunity Briefs
- Ranked backlog of opportunities
- Preliminary UX Concepts
- Workflow optimization blueprints
- Internal process automation specs
- Organizational readiness assessments
Cross-Cutting Foundations
- • Data Lakehouse blueprint
- • Identified Opportunity Briefs will also be graded on modularity to coincide with Apex Rewrite / Feasibility Assessment
- • AI privacy/compliance architecture
- • GenAI and Traditional AI / Predictive Analytics Opportunities
The Process: Our Collaborative Journey
We follow a proven, four-step sprint methodology designed for rapid learning and continuous alignment. Each phase builds upon the previous, ensuring continuous feedback and stakeholder alignment.
Step 1: Executive Strategy Alignment
Duration: 1-2 hours of the team's time
Participants
- •Chief Executive Officer, MDI
- •Board Member, MDI
- •PressW Strategy Leadership
- •PressW Solutions Architect
Objectives
- •Establish alignment on AWS Capital's investment thesis and intended exit strategy
- •Define MDI's long-term growth objectives and value creation pathway
- •Secure senior executive sponsorship for this AI transformation program
- •Discuss and align on MDI Custmer Conference and PressW's AI Representation role
Step 2: Partnership Kickoff Session
Duration: 1 hour kickoff session
Agenda
-
1
Introductions & Role Alignment:
Brief overview of each attendee's role in the organization. Identify any key stakeholders not currently represented.
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2
Internal Champion Perspective:
Articulate enthusiasm for the initiative and cultural alignment as innovation leader in the space. Describe expectations and desired outcomes from the partnership. Share a high-level vision of how AI can drive organizational transformation.
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3
PressW Engagement Overview:
Introduction to our structured methodology: People, Process, Tools. Overview of the roadmap development process and expected deliverables.
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4
Stakeholder Identifications:
Define cross-functional leaders to engage in subsequent sessions.
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5
Vision Setting:
"Art of the Possible" (10 minutes). Highlight transformational AI use cases from relevant industries. Help strategic thinking and uncover latent potential.
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6
Next Steps:
Confirm scheduling of departmental discovery sessions. Establish cadence for ongoing collaboration.
Step 3: Departmental Workflow Discovery Sessions
Duration: 1-2 hour per session. These will be virtual sessions.
Participants
Department heads and process owners
Purpose
- •Gain a granular understanding of current state workflows and business processes
- •Identify operational bottlenecks, redundancies, and sources of friction
- •Surface internal best practices that can be scaled through AI
Discussion Topics
- •What are your core responsibilities and key workflows?
- •What challenges or inefficiencies do you encounter?
- •What aspects of your workflow are highly effective, and why?
- •Where do you see potential for automation, augmentation, or acceleration?
Step 4: Targeted Deep Dive Workshops
Duration: 1-4 hours per session
These workshops will focus on validating findings from discovery sessions, co-creating potential AI solutions, and synthesizing all gathered information into the final opportunity backlog and roadmap. This phase is highly iterative and collaborative, ensuring solutions are practical and aligned with MDI's needs.
Key Process Principles
- Iterative feedback loops
- Stakeholder alignment checkpoints
- Evidence-based prioritization
Success Enablers
- Cross-functional team engagement
- Technical feasibility validation
- Rapid prototyping where applicable
The Outcomes: Deliverables & Roadmap
This engagement will produce tangible assets to guide your AI journey. Below is a list of key deliverables and an interactive 18-month roadmap that visualizes the path from quick wins to long-term strategic plays.
Key Deliverables
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🎯
AI Representation at MDI Customer Conference September 22-23
- ✓ MDI AI Opportunity Backlog & Prioritization Matrix
- ✓ 18-Month Roadmap + Quick Wins
- ✓ Oracle APEX Modernization Options Deck
- ✓ Lightweight Measurement & Governance Template
- ✓ Concept Assets
Interactive 18-Month Roadmap
This timeline illustrates the phased rollout of AI initiatives. Hover over each bar for more details.
Core Team: Roles & Governance
A successful partnership requires a well-defined team structure. This table outlines the key roles from PressW, MDI, and AWS Capital who will guide this initiative.
| Role | Organization | Key Responsibility |
|---|---|---|
| Strategy Lead | PressW | PM, strategic roadmap lead |
| AI Solutions Architect | PressW | MDI tech review & mapping, technical roadmap owner |
| Internal Champion (Danny) | MDI | Domain SME, system walkthroughs |
| COO Sponsor (Shannon) | MDI | Steering, Block Remover |
| Board Sponsor & Strategy Partner | AWS Capital | Investment thesis & exit strategy alignment |
Assumptions & Risks
To ensure a smooth and successful engagement, we are proceeding with the following assumptions and have identified potential risks with mitigation strategies.
Key Expectations
- ✓Stakeholder Access: Required stakeholders will be available for approximately 2 hours per week.
- ✓No Live PII: No live Personally Identifiable Information will be processed during the sprint.
- ✓System Access: High-level architecture documents and source access for Apex will be available.
- ✓Anticipated Decisions: Final investment and hiring decisions will be addressed after the roadmap is complete.
Risks & Mitigations
| Risk | Mitigation Strategy |
|---|---|
| Scope creep into PoC build | All concept work is explicitly time-boxed. |
| Metrics misalignment | KPIs will be co-defined after opportunity validation. |
| Stakeholder bandwidth | Use async tools (Loom) and escalate via SteerCo. |
| Technical unknowns (Apex) | Engage SMEs first, then use AI code interpreters as secondary support. |
Forward Actions
Let's take the next steps to finalize our partnership and kick off this transformative project.
- 1Confirm this SOW and agree on pricing
- 2Finalize NDA / MSA
- 3Schedule Kickoff (Target: Monday, August 4)
- 4Share available system docs & architecture diagrams
- 5Identify initial key stakeholders (starting with Danny)