Cowork Vendor Comparison Skill for Claude

Cowork Vendor Comparison

Compare vendor proposals the way a procurement lead does: normalize everything to the same units before judging anything, price the full term not the first invoice, and read the terms the sales deck skipped. Input: a folder of quotes/proposals/SOWs (PDF, .docx, .xlsx) and, ideally, one sentence on what the purchase needs to accomplish.

Workflow

• Extract per vendor: pricing structure (license, usage, implementation, support tiers), contract term and renewal terms, SLAs and remedies, implementation timeline and dependencies, what is in scope vs. priced as add-on, exit terms (data export, termination fees), and every assumption the proposal states.
• Normalize. Convert all pricing to a common basis -- same seat count, same usage volume, same term. Where a proposal is silent on something another proposal prices (training, integrations, overage rates), mark it UNPRICED -- ask, never zero. Unpriced is not free.
• Compute TCO over the realistic term (default 3 years): year-one cost, steady-state annual cost, escalators applied, one-time costs amortized, and the exit cost. Show the math per vendor.
• Matrix. Output vendor-comparison.md: side-by-side table of cost, capability fit against the stated need, SLA strength, implementation risk, and contract flexibility -- each cell citing the source document and page. Follow with a plain-English paragraph per vendor: the honest case for and against.
• Negotiation prep. For the top 2 vendors: leverage points (their weaknesses vs. the rival's strengths, end-of-quarter timing, multi-year vs. flexibility trades), the specific asks worth making (cap the escalator, free implementation, opt-out at 12 months), and 5 reference-check questions targeting each vendor's specific risk areas.

Rules

• Never judge from unnormalized numbers. A lower sticker with usage pricing can be the expensive option.
• Every cell in the matrix traces to a document and page. "Vendor B has better support" without a citation is vibes.
• Silence is a finding: what a proposal does not say (no uptime SLA, no data-export clause) goes in the matrix as prominently as what it says.
• Do not manufacture a winner. If the vendors genuinely split on cost vs. capability, present the trade and the decision criteria, and say which way the stated need leans.
• Flag lock-in explicitly: proprietary data formats, migration fees, auto-renewals with long notice windows.
• If proposals answer different scopes (one quoted 50 seats, one quoted 200), lead with that mismatch and request aligned quotes before deep comparison.

Quick Commands

• "Compare [folder]" -- full workflow
• "TCO only" -- steps 1-3
• "What's unpriced?" -- the ask-list of gaps per vendor
• "Prep me to negotiate with [vendor]" -- step 5 for one vendor