Point it at the mess. Bulk-upload a Google Drive folder, a desktop pile, or a two-year document dump, and AI auto-indexing sorts every file into the standard 8-category due-diligence structure — Corporate, Financial, Legal, IP, Team, Product, Cap Table, Tax — in under 3 minutes. AI room generation can build a room straight from a document dump; AI document Q&A lets reviewers ask questions of the documents. You review the draft, set permissions, and share NDA-gated links. Median setup from account creation to first upload is 4 minutes 19 seconds. $52 per admin per month on Peony Data Room — unlimited documents, rooms, storage, and viewers.
Building a data room with AI means you skip the manual folder assembly. Instead of creating an eight-folder tree by hand and dragging files into it — the part founders and advisors dread — you bulk-upload your documents in whatever disorganized state they arrive, and AI auto-indexing reads each file and sorts it into the standard 8-category due-diligence structure — Corporate, Financial, Legal, IP, Team, Product, Cap Table, and Tax — in under 3 minutes for a typical document set. It flags categories that look thin, so a missing IP assignment or an absent cap table surfaces before an investor's counsel finds it. The typical path is a mess in, a reviewed index out: a founder's Google Drive or a partner's desktop becomes a numbered, deal-ready room.
On Peony there are three distinct AI capabilities, and it's worth keeping them straight. AI auto-indexing sorts the bulk upload into the standard structure. AI room generation stands up a room end-to-end from a document dump when you want the room built rather than folder-by-folder. AI document Q&A lets a reviewer ask a question and get an answer drawn from the documents in the room — grounded in what's been shared, not the open internet, so a buy-side reviewer can trace every answer back to a source they can open. AI auto-indexing and AI room generation are on the Data Room plan at $52 per admin per month; AI document Q&A is on the Business plan at $30 per admin per month.
The honest boundary is the same one that makes the AI trustworthy: it categorizes, and you verify. On a typical upload the AI sorts the clear majority correctly and misses a small handful of edge cases — a document that belongs in two categories, a cryptically named file, a one-off the standard structure doesn't anticipate. Moving those strays takes about a minute; the final structure is your responsibility, not the model's. What the AI removes is the hours of manual sorting, not the five-minute review — and it should not remove that review. This is why a chat tool alone isn't a data room: a chat tool can suggest an outline, but only the room itself can host the files, gate them behind an NDA, watermark each page, and prove who read what.
AI auto-indexing and AI room generation run on the Data Room plan at $52/admin/month; AI document Q&A runs on the Business plan at $30/admin/month. Across every AI step the pattern is the same: the AI drafts the structure in minutes, you review the few strays and lock down the sensitive folders. The final index is yours to confirm before you share it.
Scattered Drive and desktop docs bulk-uploaded, AI-indexed into the 8-category structure, NDA-gated before a term-sheet meeting.
One AI-built room per concurrent sell-side, unlimited rooms on a single plan, dynamic watermarks per bidder track.
A room the AI builds from a document dump continues as an LP-reporting room through the hold period at the same flat rate.
A one-off SPV or property raise: bulk upload, AI structure, one deal room, unlimited free viewers, staged access.
Standardize every acquisition room to one AI-generated baseline structure, so diligence indexes look identical across targets.
Client financials bulk-uploaded and AI-sorted into a clean index, shared under watermark with reviewers and lenders.
When you only need a naming outline. If all you want is a suggested folder list, a general chat tool can draft one. Organizing is the easy 10% — but a chat tool can't host, gate, watermark, or log access, so you'll still need a room to put the files in. The AI is the setup speed; the room is the product.
When the room is tiny and low-sensitivity. A single document sent to one reviewer once doesn't need auto-indexing at all — a watermarked personalized link is enough. Don't build an AI-indexed room for a one-file share.
When you need Q&A but not watermarks yet. If your priority is letting reviewers self-serve answers and the room is low-sensitivity, AI document Q&A on the Business plan at $30/admin/month is a legitimate cheaper start — auto-indexing and watermarking come with Data Room at $52.
When the structure has to be exact and non-standard. The AI produces the standard 8-category tree. If your firm's playbook requires a specific non-standard structure, you'll build that yourself on top of the AI's baseline — the AI gets you to the standard fast, your template layers over it.
When you'd skip the review. The AI categorizes, you verify — that's not optional. If you're not willing to open every folder and move the few strays before sharing with investors, no tool will save you. The final structure is your responsibility.
"Peony has been great for sharing documents with investors, employees, and customers. It's easy to use, good value, and new features are constantly being added. Definitely recommend!"

Ed Harris
Founder & CEO, Ligo Bio (YC S24)
Yes, and the weekend is more than enough. Pull everything into one place — cap table, SAFEs, financial model, incorporation docs, IP assignments, pitch deck — and bulk-upload the whole pile to Peony without organizing it first. AI auto-indexing sorts the upload into the standard 8-category due-diligence folder structure (Corporate, Financial, Legal, IP, Team, Product, Cap Table, Tax) in under 3 minutes, and flags categories that look thin so you notice the missing IP assignment before an investor does. Median setup from account creation to first upload is 4 minutes 19 seconds. AI auto-indexing lives on the Data Room plan at $52/admin/month, which is also where dynamic watermarking, Advanced NDA with countersigning, and granular permissions live — so by Monday you have a numbered, NDA-gated room instead of a Drive link that reads as unprepared. The honest part: the AI categorizes, you verify. Budget ten minutes to move the two or three files it puts in the wrong folder and to rename anything cryptic — the final structure is your call, not the model's.
Each listing is its own room, and each one starts the same way: dump the seller's document set in, let AI auto-indexing build the folder structure, spend ten minutes reviewing. Instead of assembling three diligence indexes by hand you're reviewing three the AI already drafted — the standard 8-category structure comes back in under 3 minutes per room. On the Data Room plan at $52/admin/month you get unlimited rooms, so three concurrent listings cost the same as one, with dynamic watermarks stamping every page with the bidder's identity and granular permissions segregating what each bidder track sees. AI room generation can stand up a room straight from a document dump when you want the room built end-to-end rather than folder-by-folder. Where a solo advisor still carries the load: the AI does not know your deal's confidentiality tiering — which bidder sees the customer contracts versus only the teaser — so you set the visitor groups. The AI gives you back the hours you'd have spent dragging files into folders; the judgment stays yours.
A 140-file folder with two years of drift is exactly the input AI auto-indexing is built for. Download the Drive folder — the hierarchy is preserved on export — bulk-upload all 140 files at once, and the AI reads each document and sorts it into the standard 8-category structure in under 3 minutes rather than you triaging file names one by one. It flags categories that look empty, so if two years of ad-hoc storage never captured a clean cap table or the 409A, you see the gap before your lead investor's counsel does. One watch-out on Drive exports: Google can rename duplicate files, so spot-check names after upload. This runs on the Data Room plan at $52/admin/month, which adds dynamic watermarking, Advanced NDA with countersigning, and granular permissions for staged investor access. Honest limit: the AI categorizes by document content, not by your internal politics about what's shareable — you review the tree and lock down the sensitive folders yourself. Expect ten to fifteen minutes of cleanup on a folder that disorganized, versus the day it takes by hand.
For naming ideas and a proposed folder outline, yes — a general chat tool can suggest a structure, and there's no shame in using it that way. But organizing is the easy 10% of the job. A chat tool cannot host the files behind a link, gate them behind an NDA, watermark each page with the viewer's identity, block and log screenshots, or tell you which investor read the cap table for eight minutes and skipped the roadmap. The room is the product; the AI is the setup speed. On Peony the AI does the same categorization inside the place the documents actually live and get shared: AI auto-indexing sorts your bulk upload into the standard 8-category structure in under 3 minutes, then Data Room at $52/admin/month wraps it in dynamic watermarking, Advanced NDA with countersigning, granular permissions, and page-level analytics. So the honest framing is: use a chat tool to brainstorm the outline if you like, but you still need somewhere to put the files that can enforce who sees what and prove who saw it. That somewhere is the data room.
It does, because AI auto-indexing sorts every upload into the same standard 8-category due-diligence structure regardless of how each portfolio company handed you their files. One company's tidy SharePoint and another's chaotic desktop both come back as the same numbered tree in under 3 minutes, which is what you want when a deal partner opens six portfolio-company rooms and expects them to look identical. AI room generation can stand a room up from a document dump when you're onboarding a new company from scratch. This runs on the Data Room plan at $52/admin/month with unlimited rooms, so standardizing across a portfolio doesn't multiply your bill, and granular permissions plus dynamic watermarking apply uniformly across every room. Where you still steer: the AI produces the standard structure, but any portfolio-specific folder your firm's playbook requires — a particular ESG or KPI tab — you add and enforce yourself. The AI gets every room to the same baseline fast; your template layers on top.
Good instinct, and the honest answer is that the AI categorizes and you verify — the final structure is your responsibility, not the model's. In practice it sorts the clear majority of a startup document set correctly into the standard 8 categories in under 3 minutes, and the misses are usually edge cases: a document that legitimately belongs in two categories (an advisor agreement that's both Legal and Team), a file with a cryptic name it has to guess from, or a one-off your company has that the standard structure doesn't anticipate. On a typical upload that's a small handful of files to move, which takes about a minute, plus a few minutes to rename anything unclear. It also flags categories that look thin, which is a feature, not an error — that's how you catch a genuinely missing document versus one the AI merely filed elsewhere. So don't blindly trust it: open every folder, move the few strays, and rename for clarity before you share. The AI removes the hours of manual sorting; it doesn't remove the five-minute review, and you shouldn't want it to.
They're two different AI capabilities on two different plans, so it's worth being precise. AI document Q&A — where a reviewer asks a question and gets an answer drawn from the documents in the room — is on the Business plan at $30/admin/month ($44 monthly). AI auto-indexing, the feature that sorts your bulk upload into the standard 8-category structure in under 3 minutes, is on the Data Room plan at $52/admin/month ($75 monthly), alongside dynamic watermarking, Advanced NDA with countersigning, granular permissions, custom domain, and AI room generation. So if your priority is letting reviewers self-serve answers, Business covers it; if you also want the AI to build the folder structure and you want watermarking and the Advanced NDA, you're on Data Room. Most advisors running real diligence end up on Data Room because the watermarking and countersigning NDA matter as much as the Q&A — but if the room is small and low-sensitivity, Business with AI document Q&A is a legitimate cheaper starting point.
Scoped to the room. AI document Q&A answers from the documents in that data room — a reviewer asks a question and the answer is drawn from the files that have been shared, not from the open web, so it can't invent facts the seller never put in front of you. That matters on the buy-side for exactly the reason you're asking: an answer is only useful in diligence if it traces back to something in the room you can then open and verify yourself. AI document Q&A is on the Business plan at $30/admin/month; the Data Room plan at $52/admin/month adds dynamic watermarking, Advanced NDA with countersigning, granular permissions, AI auto-indexing, and AI room generation on top. The honest caveat: grounded-to-the-documents means the AI is only as complete as what's been uploaded — if a document isn't in the room, the AI won't answer from it, which is a feature for trust but a reminder to confirm the index is complete before you lean on the Q&A. Treat it as a fast way to locate and summarize what's there, then read the source document for anything that moves the deal.
How the AI sorts a bulk upload into the standard 8-category due-diligence structure in under 3 minutes.
The room itself: NDA gates, dynamic watermarks, granular permissions, and per-viewer audit trails.
The 60-document, 8-category standard VCs expect — the structure the AI builds toward.
The tab-by-tab build spec for a seed raise — the operator core the AI-built room starts from.
Free, Business at $30, and Data Room at $52 per admin per month — which AI capability lives on which plan.
Data rooms by file type and workflow — CAD, BIM, DICOM, drone, point cloud, geological, and more.