Paid-only drafting workspace

Pricing

Choose the plan that matches how seriously you apply.

WinProposal is built as a paid drafting workflow from day one — structured plans, clean usage limits, and a premium proposal process that stays focused on real client work.

No free tier distractionsUpgrade when your volume growsCancel anytime through your account

Recommended plan

Pro

Most popular

The best fit for freelancers who are applying consistently and want enough room to generate, refine, and iterate without hitting the ceiling too quickly.

120 proposals / month
Advanced AI drafting tier
Upgrade path stays intact if volume grows

Plans

Pick the capacity that fits your workflow.

Same product direction, different monthly capacity. The composition here stays premium, but the logic remains exactly tied to the live checkout and subscription flow.

Start clean

Starter

Best for early paid usage
$9/month

30 proposals / month

For freelancers who want a focused drafting workflow with a modest monthly volume.

30 proposal drafts each month
Saved history and usage tracking
Standard AI drafting tier
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Most balanced

Pro

Most popular
$19/month

120 proposals / month

For higher-volume freelancers who need more drafting capacity without changing their workflow.

120 proposal drafts each month
More room for active client outreach
Advanced AI drafting tier
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Highest capacity

Agency

Unlimited workflow
$49/month

Unlimited proposals

For teams or high-output freelancers who want unlimited monthly drafting access.

Unlimited proposal drafting
Best AI tier for highest-volume usage
Built for teams or nonstop outreach
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Paid-only by design

WinProposal stays focused on serious freelancer usage — no free-tier clutter, no confused plan boundaries, and no hidden usage model.

Upgrade without friction

When your volume grows, your upgrade path stays inside the same live billing flow already in production today.

Usage stays visible

Plan, status, and monthly proposal capacity remain visible so the product feels controlled rather than opaque.