Win more gigs on Upwork — without the grind
WinTheGig reads any job post and writes a hyper-personalized, human-sounding proposal in about two seconds. Paste, refine, send — and watch your reply rate climb.
No credit card required · 3 proposals on us
Acme Inc.
Payment verified · $12k+ spent
Proposal draft
Hi Dana — the moment I saw Acme needs a React dashboard with live data refresh, I knew this was my kind of build.
I shipped a similar analytics console for a fintech team last quarter: 12 charts, sub-second updates, 40k sessions a day. I'd start by mapping your data sources, then build a component system your team can extend.
Can I send over a quick Loom of that work this week?
How it works
Three steps to your next gig
No templates, no writer's block. Just your strongest pitch, ready to send.
Paste the job
Drop in any Upwork job post — link or plain text. We parse the client's real needs, tone, and must-haves in under a second.
Add your edge
Tell us your best wins, skills, and rate. WinTheGig weaves your proof into the pitch — no generic filler, no AI clichés.
Win the gig
Send a proposal that reads like you wrote it by hand. Track replies, interviews, and wins as your pipeline grows.
Features
Built to make you look like the obvious hire
Every feature is designed around one metric: replies that turn into interviews.
Hyper-personalized proposals
Every proposal is written for that exact job — the client's stack, budget, and pain points, woven into a pitch that feels handcrafted.
Natural human writing
A compact Llama humanizer strips the AI tell: varied rhythm, real specifics, zero fluff. Reads naturally in 20+ languages.
Chrome extension
Autofill your proposal inside Upwork in one click. Generate, personalize, and send — without leaving the job page.
Win-rate analytics
Watch your full funnel — sent, replies, interviews, won. See exactly what's landing gigs, then double down on it.
Job alerts
Get pinged the moment a job matches your skills and rate — before the crowd of 50+ proposals shows up.
Priority AI
Our Gemma 4 26B pipeline with priority queue keeps your proposals sharp, fast, and first in line — even at peak hours.
Bring your own API key
SoonPrefer your own model? Route WinTheGig through your key and keep full control of your stack. On the roadmap.
Pricing
Pick your plan. Win your next gig.
Start free — no card required. Upgrade when the replies start rolling in.
Free
Test the waters
Free forever
- 3 proposals total
- 72-hour trial at signup
- 5 generations + 2 refinements in trial
- 1,000-char job posts
- 1 refinement per proposal
Starter
The ticket
billed monthly
- 40 proposals /mo
- 2,000-char job posts
- 2 refinements per proposal
Pro
For the regulars
billed monthly
- 100 proposals /mo
- 2,000-char job posts
- 2 refinements per proposal
- Chrome extension
Max
For full-time winners
billed monthly
= $0.04 per proposal
- 300 proposals /mo
- 3,500-char job posts
- 3 refinements per proposal
- Chrome extension
- Win-rate analytics
- Job alerts
- Priority AI — Gemma 4 26B + humanizer
Popcorn add-ons
Grab extras anytime — no plan change
Comparison
Why freelancers switch
Max versus the generic AI tools. The math speaks for itself.
| Feature | WinTheGig MaxRecommended | Other AI tools |
|---|---|---|
| Price per proposal | $0.04 | $0.08 – $0.10 |
| Chrome extension | Included | Not included |
| Human-style writing | Native | Sometimes |
| Win-rate analytics | Built in | Not included |
| Job alerts | Included | Not included |
| Multi-language | 20+ languages | Limited |
Early user feedback
Freelancers are already winning
The first crew on WinTheGig — here's what they're seeing.
Sent 12 proposals in one weekend. Four replies, two interviews, one signed contract. This thing pays for itself on day one.
The tone is scary good — clients think I wrote every word. I tweak a sentence, hit send, and move on with my day.
I stopped dreading job hunting. Paste, refine, send. My reply rate tripled in three weeks and the gigs got bigger.
FAQ
Questions, answered
Everything freelancers ask before their first proposal. Still curious? We reply within a day.
Yes. WinTheGig helps you draft proposals — you review, edit, and send them yourself. The output is written to read as human and naturally personalized, and we never post or bid on your behalf. Thousands of freelancers use AI drafting tools every day; we keep yours clean, original, and on-brand.
One credit = one generated proposal. Paid plans include a monthly credit allowance, and refinements count within your plan's limits. Your 72-hour trial gives you 5 generations and 2 refinements — after that, the Free plan keeps you going with 3 proposals total. Credits reset monthly on paid plans.
You land on the Free plan automatically — no card, no surprise charges. You keep your 3 proposals, and you can upgrade to Starter, Pro, or Max whenever a great gig shows up.
The extension is included with Pro and Max. It autofills your generated proposal right inside Upwork, so you can paste, tweak, and send without leaving the job page.
Not yet — but BYOK is on the roadmap. We're building it so you can route generations through your own key and keep full control of your stack. Join the waitlist in the app to get it first.
WinTheGig is a digital service that's delivered instantly, so we don't offer refunds. But you can cancel anytime — you'll keep access until the end of your billing period, and the Free plan is yours forever.