ClientWin OS vs Proposify

ClientWin OS is web-based AI proposal software for freelancers, solo consultants, small agencies and other service providers. Its workflow checks opportunity fit, guides pricing, matches relevant proof, drafts a proposal, shares a Client Deal Room link and tracks responses and outcomes. Users review and send every proposal themselves; the product says it does not scrape platforms or submit proposals automatically. The Free plan is billed at $0 per month and includes one proposal generation, five AI Actions, three manual Proof Vault items and basic PDF or share export. Starter costs $13 a month, Pro costs $26 a month and Agency costs $68 a month. Paid plans increase monthly allowances and add capabilities such as proof import, branded exports, client rooms, automated workflow and team collaboration. Proposal generations and AI Actions have separate allowances; automated workflow on Pro and Agency uses those same allowances. Private workspace data is not used to train public AI models, though relevant data may be sent to third-party AI providers. Platform Intelligence is off by default.

Proposify is a web app for sales teams to create, send, track, and close customized proposals. Its drag-and-drop editor handles text, images, video, tables, and shapes, and interactive quotes let buyers select optional fees or enter quantities. Document analytics show when recipients open a proposal and how long they spend in each section. Documents can be created without a plan limit, though monthly send allowances vary: Basic includes 10, Team 30, and Business 75. All plans allow legal e-signatures, and the service supports online payment collection, custom branding, and CRM integrations. Proposals are created and sent in the web app; an iOS companion app monitors proposal activity. A 14-day trial includes Team plan features. Basic costs $19/user/mo when billed annually, while Basic monthly costs $29/user/mo and Team quarterly costs $49/user/mo. The company states that proposals use encrypted links and 256-bit SSL security, and that it is GDPR compliant and SOC 2 Type 2 certified.