AI-Powered Bidding for Upwork

Know Your Odds.
Bid With Proof.

Before you spend a Connect, UpBidAI scores your win chance against the job and generates a proposal grounded in your actual portfolio.

< 2s
Win Chance scored
100%
Portfolio-backed proposals
$0
To get started
UpBidAI - Chrome Extension
Senior Flutter Developer - Cross-platform Mobile App
$4,000 - $8,000Fixed PriceExpert
FlutterDartFirebaseREST APIs
89%
Win Chance
Strong portfolio match - 4 projects
EXCELLENT
Top matching portfolio
Fintech App - Flutter + Firebase94%
E-commerce Mobile - Dart/REST88%
Health Tracker - Cross-platform81%
Proposal injected into apply form
Generated in 4.1 seconds
The Real Problem

Most proposals fail before you write a word.

You bid on the wrong job. You find out three days later when the client does not reply. You spent 6-12 Connects to learn that. There was no signal - just instinct and hope.

01 · The Surface Pain

Writing proposals takes too long

30-60 minutes per tailored proposal. Scale that to 10 bids a week and proposal writing becomes a part-time job - before you have won anything.

Speed problem
02 · The Real Problem

You're bidding blind on expensive jobs

Upwork Connects are not free. Bidding 6-12 Connects on a job you have a 5% shot at is not a writing problem - it is a targeting problem. There is no signal before you spend.

Selection problem
03 · The Hidden Problem

Your best work never compounds

The portfolio that should be winning you jobs is disconnected from your bidding workflow. Every proposal starts from zero. No proposal teaches the next one anything.

Feedback loop problem
How It Works

Portfolio in. Win Chance out. Proposal written.

Three steps from first login to a proposal already waiting in the apply page.

1

Sync Your Portfolio

Connect your Upwork profiles and add portfolio items. The system chunks, embeds, and indexes every project into your personal vector store using the same AI models that power the search.

One-time setup · under 5 minutes
2

Score Before You Bid

Open any job on Upwork. The Chrome Extension computes your Win Chance in under 2 seconds - vector similarity between the job description and your indexed portfolio. See the tier before you spend a Connect.

Real match signal · not keywords
3

Generate With Proof

Trigger generation from the extension. The system retrieves your top-matching portfolio items, injects them as context, and writes a proposal that references your real past work. It is waiting in the apply textarea.

RAG-grounded · not generic AI text
What goes into every proposal
Upwork Profile
Structured context
+
Portfolio Items
Top-N vector matches
Key differentiator
+
Proposal History
Structured context
+
Job Description
Structured context
Output
Proposal Generated

Portfolio items are retrieved per job, so each proposal is specific to that posting rather than generic template text.

Features

Every feature solves a real bidding problem.

No bloat. Every capability maps to a specific bottleneck in the freelance bidding workflow.

Win Chance Indicator

Before you spend a Connect, you see a score. It is computed by embedding the job description and running vector similarity against your indexed portfolio - not keywords, not vibes. The score is tiered so the decision is instant.

Vector similarity · Weaviate search · per Upwork profile
Low - skipMediumHighExcellent - bid now

Tiers are computed per job, per profile, per run.

Portfolio-Grounded Proposals

The AI does not write from general training data. It retrieves your top-N matching portfolio items and injects them as context. The proposal cites real projects because the system literally searched for them.

RAG architecture · OpenAI embeddings

Proposal History & Outcomes

Every generated proposal is saved with its outcome - Won, Lost, No Response, or Submitted. Tag proposals with a quality rating. Over time, you see exactly which prompt styles and job types correlate with wins.

ProposalRecord · per-preset win rate stats

Multi-Segment Prompt Presets

Every proposal is composed of four named segments: Opening Hook, Relevance Bridge, Portfolio Showcase, and Call to Action - each independently configurable. Create multiple presets per profile. A/B test by job type.

Configurable per segment · saved presets

Agency Command Center

Teams share a portfolio RAG pool. Every bidder pitches from the same portfolio depth. Set per-member monthly usage limits. See proposal activity and win rates per team member.

Role-based access · per-bidder spend caps
Chrome Extension

The proposal is already in the apply box.

The extension runs natively inside Upwork, scores your fit, and injects the generated proposal into the cover letter textarea.

  • Win Chance overlay on every job pageScore appears the moment you open a job. Excellent match? Generate immediately. Low match? Move on.
  • Top matching portfolio shown per jobYou see exactly which of your projects drove the score - and those same projects become the proposal context.
  • Auto-inject into Upwork apply textareaNo tab switching. No copy-paste. Select your prompt preset, click Generate - the proposal fills the box.
  • Submission detection and syncWhen you submit, the extension detects it and logs the proposal as Submitted - no manual tracking needed.
Add to Chrome - Free
UpBidAI Extension
Senior Flutter Developer - Cross-platform App
$4,000 - $8,000 · Expert · Fixed price
Win Chance
89%
EXCELLENT
Matched Portfolio
Fintech App - Flutter + Firebase94%
E-commerce Mobile - Dart/REST88%
Health Tracker - Cross-platform81%
Proposal injected
Cover letter ready - 4.1 seconds
< 2s
Win Chance scored per job
4
Proposal segments independently tuned
100%
Portfolio-grounded proposals
$0
To start with Free
From Freelancers

What changed when they stopped bidding blind.

I was writing 10 proposals a week and winning maybe one. The problem was not my writing - it was that I was bidding on jobs where my portfolio did not match. Win Chance told me that on day one.

AR
Arjun R.
Full-stack Developer · Top Rated

Clients used to ghost my ChatGPT proposals. With UpBidAI, the proposal mentions my real Fintech app and React Native work because the system actually found what is relevant. Clients respond to specifics.

SM
Sofia M.
Mobile Developer · Expert-Vetted

We run a 6-person agency. Before this, every bidder had their own style and we could not standardize. Now everyone bids from the same portfolio database and I can see win rates per team member.

DK
Darius K.
Agency Owner · 6-person team
Pricing

Pick the plan that wins
you more work.

Start free, forever. Upgrade when you're ready to bid at scale.

Free

Start scoring jobs and generating proposals. No credit card needed.

$0/ month

Free forever

Get Started Free
Monthly UsageStarter access
Enough to evaluate, score, and win your first jobs

What's included

  • Win Chance scoringIncluded
  • Portfolio items5 max
  • Upwork profiles2 profiles
  • Prompt presets3 presets
  • Proposal historyIncluded
  • Team membersNot included
  • Usage top-upPro only
  • Email notificationsPro only
Most Popular
Pro

Unlimited portfolios, team access, top-up wallet, and full analytics.

$10/ month

Billed monthly

Start Pro Free for 7 Days
Monthly UsageFull access
Built for freelancers bidding daily

Everything in Free, plus

  • Portfolio itemsUnlimited
  • Upwork profilesUnlimited
  • Prompt presetsUnlimited
  • Team membersWith spend caps
  • Usage top-upCarry-over balance
  • Full analyticsWin rate per preset
  • Email notificationsConfigurable threshold
  • Priority supportIncluded
No credit card to startCancel anytimeWallet balance never expiresReal humans on support

Out of usage mid-month on Pro? Top up anytime - extra capacity available in the dashboard. Your balance carries over every cycle.

Stop bidding blind.
Start bidding with proof.

Your portfolio is the context. UpBidAI connects it to every job you open and shows your odds before you spend a Connect.

Start free · No credit card required · Upgrade anytime