Diligence — How-Tos & Workflows

Start a workspace

1. Go to Diligence.
2. Click New Workspace.
3. Enter the company name and, if it exists in your Deal Pipeline, optionally link it to that deal.
4. Save.

Upload a document

1. Open the workspace and go to the Documents tab.
2. Choose a category (Financial Statements, Legal, Cap Table, Management, Market Analysis, Technical, or Other) and upload your file.
3. The document appears in the Document Vault under its category, with a status of pending, uploaded, reviewed, or flagged.

Uploads are limited to 25 MB per file.

Preview a document

In the Documents tab, select a document in the Document Vault. PDFs and images (PNG, JPG, GIF, WEBP, SVG) preview directly in the workspace. Word, Excel, and PowerPoint files preview through Google Docs Viewer — see Advanced & Customization for what that means for the document's privacy. Use Open in new tab to download any document directly.

Extract financial metrics

1. Open a workspace that has at least one uploaded document.
2. Go to AI Analysis → Financial Extraction.
3. Click Extract Metrics. Cairn Intelligence reads your uploaded documents and returns what it can find: ARR, revenue, revenue growth, gross margin, NRR, burn rate, runway, headcount, and a short summary.
4. Run it again any time — click Re-extract to refresh the metrics after uploading new documents. Each run replaces the previous result.

Example: checking a deck's numbers. The Lumen Health deck claims "$8M ARR". After uploading the deck and the latest management accounts, Extract Metrics returns ARR of $6.1M, because that's what the management accounts say. The difference is visible before anyone repeats the deck's number in a memo, and Generate Thesis then quotes the exact line it comes from.

Generate an Investment Brief

Needs Run Cairn Intelligence (Admin, Partner, or Analyst). Viewers can read a brief but not generate one or edit its notes.

1. Open a workspace that has at least one uploaded document.
2. Go to AI Analysis and choose Investment Brief.
3. Click Generate brief. Cairn Intelligence reads your documents and returns:
   • a summary of strengths, risks surfaced, and open questions;
   • key findings, each with View supporting evidence showing the exact quotes, and a link that opens the source document;
   • questions to resolve with management;
   • document coverage, showing which documents were read in full and which only in part.
4. Add your interpretation in Analyst notes and click Save notes. Save before regenerating; your saved notes carry over.
5. If documents change, the brief shows a warning. Click Regenerate brief to use the current documents.
6. Click Download PDF to share it.

Example: preparing for a first partner call. Lumen Health's data room has 40 documents and the partner has 20 minutes. The analyst generates a brief: two strengths (a 130% net revenue retention figure and a three-year hospital contract), one risk (40% of revenue from one customer), and three questions, including "Can management share the renewal terms for the largest customer?". Each finding opens to the quote it came from, so the partner can trust it without reading the deck. The analyst adds a note on what they want to test, and the partner takes the questions into the call.

Generate a Cairn Thesis

1. Open a workspace that has at least one uploaded document.
2. Go to AI Analysis → Cairn Thesis.
3. Click Generate Thesis. Cairn Intelligence reads your documents and returns cited findings (strengths, risks, observations) and material assumptions, each with an evidence status of supported, contradicted, or not established.
4. Set your own bear/base/bull ARR growth scenarios on the Scenarios tab, and edit any assumption's interpretation in the Assumptions tab — your edits are kept separately from what Cairn Intelligence originally found.
5. Click Regenerate Thesis any time to produce a new version. Every version is kept — use the version dropdown to browse prior theses. Your analyst notes carry forward into the new version automatically.
6. Click Download PDF to export the current version.

If a citation Cairn Intelligence returns can't be matched back to your actual document text, the generation is rejected and your previously saved thesis is left unchanged — try generating again.

Example: an assumption that doesn't hold. The thesis lists the assumption "Net revenue retention above 120%" as contradicted, quoting the customer cohort file: "2025 NRR: 104%". The analyst adds a note explaining what they'll ask management, and sets the Scenarios to 40% / 70% / 110% ARR growth for bear, base, and bull. When new documents arrive, Regenerate Thesis creates a new version; the old one stays in the version list, so the team can see how the view changed.

Generate an IC Memo

1. Make sure the workspace already has a Cairn Thesis and a Financial Extraction — IC Memo synthesizes both. If either is missing, generating a memo fails with a message telling you which one to create first.
2. Go to AI Analysis → IC Memo.
3. Click Generate Memo. Cairn Intelligence produces an executive summary, a thesis narrative, market/management/risk findings, a comparable-companies section (only populated if your documents actually mention comparable companies), a valuation section built from your Thesis's bear/base/bull scenarios, and a recommendation.
4. Add your own analyst notes in the notes field — these carry forward across regenerations.
5. Click Regenerate Memo to produce a new version once your underlying documents, Thesis, or Financial Extraction have changed. The memo flags itself as stale if any of those three have changed since it was generated.
6. Click Download DOCX to export the current version as a Word document.

Example: the night before IC. With the Thesis and Financial Extraction done, the analyst clicks Generate Memo. The draft has an executive summary, financials, risks, a valuation section built from the bear/base/bull scenarios, and a recommendation, each finding quoting the documents. The analyst edits the notes, downloads the Word file, and spends the evening on judgement rather than formatting. If someone uploads a new document afterwards, the memo shows as stale until it's regenerated.

Manage the checklist

In Checklist & Flags, add checklist items and update each item's status as you work through diligence: not started, in progress, complete, or not applicable.

Track red flags

In Checklist & Flags, add a red flag with a title, detail, severity (high, medium, or low), and optionally a source. Red flags are entered by you — Cairn Intelligence doesn't detect them automatically today.

Manage advisors

In the Advisors tab, add an advisor with their firm name, type of advisory work, scope, status, and expected completion date. Update their status or remove them as the engagement progresses.