ai-readiness

Portfolio AI Readiness

Workflow

Step 1: Connect to Portfolio Data

Ask where the portfolio materials live:

• MCP servers — data room, SharePoint, Google Drive, or a portfolio-ops database
• Local files — folder with quarterly decks, financials, board packs
• File uploads — PDFs, PowerPoint, or Excel dropped in the conversation

Pull quarterly updates, board decks, and financials. For each company extract: sector, revenue, headcount by function, tech stack, and AI/automation initiatives already in flight. If the user provides a single company, still run the scan but skip cross-portfolio ranking.

Ask up front if not obvious from materials:

• Hold period remaining per company (AI payback matters less 12 months from exit)
• Whether any portco has already deployed something that worked

Step 2: Per-Company Scan

For each company, answer three gate questions. All yes → Go. Any no → Wait with a note on what unblocks it.

1. Is the data there? Can they produce a clean input (customer list, invoice feed, claims/remits file, contract repository) without a 6-month data project first?
2. Is there an owner? Someone on the management team who will drive this, not a sponsor who will "support" it.
3. Can we pilot in 30 days? One team, one workflow, off-the-shelf tooling.

Then identify the top 2-3 leverage points:

Back Office (usually fastest to pilot)

• Invoice processing, AP/AR matching, expense categorization
• Contract abstraction — vendor agreements, leases, payor contracts, MSAs
• Month-end close: reconciliations, flux commentary, lender reporting first drafts

Revenue / Front Office

• RFP and proposal first drafts
• Sales call summaries and CRM hygiene
• Customer / patient support ticket triage and first-response drafting
• Quoting for configured / complex products
• For healthcare services: prior authorization, denials management, claim scrubbing, coding assistance, ambient clinical scribes

Operations (sector-dependent)

• SOP and quality documentation generation
• Scheduling and dispatch (field services, home health, infusion)
• Code generation and review (software portcos)

For each leverage point: what it replaces, FTE-hours/week saved (assume 30-50%, not 100%), and whether it's off-the-shelf or a light build.

Step 3: Rank Across the Portfolio

Stack every leverage point into one list. Rank by:

1. Dollar impact — annualized EBITDA contribution (cost out + revenue lift, net of tool cost)
2. Speed to value — months to first measurable result
3. Probability — discount for data quality, change management, management capability

Tiebreaker: favor opportunities with <18 months of hold period remaining.

Rank	Company	Opportunity	Est. EBITDA ($)	Months to Value	Gate	First Step
1					Go
2					Go
3					Wait — [blocker]

Step 4: Find the Replays

The highest-leverage move is running one successful play at multiple companies:

• Same sector, same function — two healthcare services portcos with manual prior-auth? One implementation, two deployments.
• Same tool, different company — if one portco has working invoice processing, every other portco with >$Xm AP volume is a fast follower.
• Shared vendor leverage — three portcos buying the same tool is a pricing conversation.

List each replay with lead company (who proves it) and followers (who copy it).

Step 5: Output

One page for the operating partner:

1. Top 5 across the portfolio — ranked table from Step 3, with owner and 30-day first step
2. Replays — 2-3 playbooks that hit multiple companies at once
3. Go / Wait by company — one line each; for Waits, what unblocks them
4. What we're NOT doing — opportunities that failed a gate; saves relitigating them every quarter
5. Aggregate EBITDA contribution — portfolio-wide opportunity, split Year 1 quick wins vs. Years 2-3 scale

Important Notes

• Rank by dollars, not excitement. Boring AP automation that saves $400k beats a flashy chatbot.
• The binding constraint is almost always data, not models. If a portco can't produce a clean customer/claims list, the first project is data cleanup.
• Off-the-shelf first. Custom builds are slow and fragile for companies without engineering depth.
• Ownership is the real gate. A quick win with no internal owner dies in 90 days.
• Hold period drives urgency. A company 12 months from exit needs something in LTM EBITDA for the CIM — or skip it.
• Failed pilots are signal. Find out why before proposing the same thing again.