ProPlaintiff

What it is

ProPlaintiff (ProPlaintiff.ai) is an AI platform for small and mid-size plaintiff personal-injury firms: it drafts demand letters, builds medical chronologies, summarizes records, and increasingly wants to be the firm’s case-management system as well. It was launched in 2023 by Kristopher Rezagholi, a practicing PI attorney, and Jason Turnquist, the co-founder of the Phoenix web agency Fyresite, who now runs ProPlaintiff as CEO. It is an early-stage company: no priced venture round has been announced, and its 2026 capital has come from angel-style strategic investors — Marc Chesley, former COO of Paradox (June 1, 2026), and Christopher Stark, co-founder of Freestar (July 17, 2026), both via company press releases with no amounts disclosed. Headcount trackers put the team at single digits in mid-2026. It was a finalist for the Phoenix Business Journal’s 2026 AZ Inno Fire Awards.

That profile matters for buying. ProPlaintiff is the low-cost, self-serve end of a category whose leaders — EvenUp, Supio, and Eve — sell enterprise contracts to firms with hundreds of open files. ProPlaintiff sells to the solo attorney and the five-person shop who want the same document types without a demo-gated, six-figure commitment. All feature and pricing claims below were checked on 2026-10-18; at this company’s stage, both move fast.

What it does

The product groups into four areas, per the vendor’s site:

• Drafting. AI demand letters, medical chronologies (visual timelines linked back to source records, with treatment dates, providers, diagnoses, and ICD codes extracted), document summaries, and a document generator for subpoenas, motions, and pleadings. The FAQ says every summarized fact links to the page and line of the uploaded source.
• Analysis. Case analysis plus media analysis of bodycam and surveillance video, depositions, and 911 calls — a feature the larger vendors do not lead with.
• Case management. An “AI Case Manager,” automations, calendar and deadline tracking, a client-care app, client texting, and AI email. “Ask Tiff,” the built-in AI paralegal, answers questions across a case file and drafts documents.
• Integrations. The FAQ names Clio, MyCase, and Filevine for importing cases and client data, plus Google Drive, Dropbox, and OneDrive. There is no public API yet; the Enterprise tier lists API integration as future work.

The concrete use case where it earns its fee: a two-attorney auto-accident practice that sends four to twenty demands a month, has no full-time paralegal for records, and wants a first-draft demand and chronology the same day the records arrive instead of three days later.

Pricing

ProPlaintiff’s own site publishes no prices — it routes buyers to a demo, and its FAQ describes per-seat subscriptions with volume discounts. Directory listings sourced from the vendor (Capterra, G2) show flat monthly tiers:

• Essentials — $99.99/month: 1 user, 4 demand letters, 40 summaries.
• Professional — $399.99/month: up to 5 users, 20 demand letters, 200 summaries.
• Enterprise — $999.99/month: 100 demand letters, 1,000 summaries; Spendbase describes it as custom pricing for 15+ users.

At list, that works out to roughly $10–25 per demand letter with summaries bundled — an order of magnitude below the ~$300-plus per demand reported for EvenUp. Real-world, a five-attorney firm should expect to land on Professional at about $4,800 a year and pay overage or upgrade once volume passes 20 demands a month. Get the tier, the demand allotment, and overage pricing in writing; the published figures are third-party listings, not a vendor price sheet.

Best for

• Solo and small (1–10 attorney) plaintiff PI firms that need demand letters and chronologies at a predictable monthly cost.
• Firms already on Clio, MyCase, or Filevine that want AI drafting bolted on without changing their system of record.
• Practices handling video-heavy matters — trucking, premises, police-involved — where media analysis saves review hours.

Alternatives

• EvenUp — the share leader in PI demand packages. Pick it when settlement value is the metric and you want a comparable-verdict database plus a human legal-review layer behind every demand; accept enterprise pricing and a sales cycle to get it.
• Supio — the other leader by funding and footprint. Pick it when the bottleneck is massive medical-record sets and you want Westlaw-grounded research in the same tool.
• Eve — the fastest-growing entrant, past a $1B valuation after a $103M Series B in 2025. Pick it when you want intake, discovery, and litigation prep on one platform, not just demand drafting.
• Precedent — per-demand pricing with a Clio integration; pick it if you send few demands and would rather pay per letter than per month.

The rule: under roughly 20 demands a month and no budget for an enterprise contract, start with ProPlaintiff. Above that, or when demand quality is the firm’s competitive edge, run a paid pilot against EvenUp or Supio before renewing.

Watch-outs

• Vendor viability. A single-digit team funded by strategic angels is a real continuity risk for a tool holding your case files. Guard: sign month-to-month or a short annual term, and test the export path on day one — the FAQ says demands, chronologies, and original files export as DOCX or PDF at any time; confirm it before you load your full caseload.
• Security claims are self-reported. The site states HIPAA compliance, a no-training policy, and US-hosted encrypted storage, but lists “SOC 2 Auditing” only as a feature label, with no audit report referenced. Guard: request a signed BAA and the SOC 2 report (or the auditor’s bridge letter) before any PHI is uploaded; no report, no PHI.
• No human review layer. Unlike EvenUp, nothing checks the draft before you see it, and the vendor’s “90% time saved per document” figure is its own marketing claim. Guard: keep attorney review mandatory on every demand, and spot-check each chronology’s source links against the record before a number goes to an adjuster.
• Case-management scope creep. The platform pushes toward replacing Clio or Filevine, which would put your system of record on the smallest vendor in your stack. Guard: use it as the drafting layer on top of your existing case-management system until the company has a longer track record.