Are you stuck in the loop of refreshing Upwork, writing similar proposals, and wondering why you’re not getting responses? You’re not alone. The competition on Upwork is fierce, and often, winning a project depends not just on your skills but on your speed, personalization, and timing. That’s a lot to juggle—especially if you’re a freelancer managing everything solo or an agency handling multiple client profiles.
This is exactly the problem Upprop.app solves. It’s a smart Chrome extension designed for freelancers, agencies, and business developers who want to automate the most time-consuming parts of Upwork outreach. It writes and sends personalized proposals for you using an AI-powered proposal assistant for Upwork—based on the job description, your profile, and even your portfolio. Think of it as a smart freelance proposal tool that helps you respond faster and smarter. The result? You show up first in a client’s inbox, with a custom-tailored pitch crafted by your automated Upwork pitch generator.
Why Traditional Upwork Tactics Are No Longer Enough
Upwork isn’t what it used to be. A few years ago, simply having a polished profile and submitting proposals regularly was enough. But today, the platform is flooded with talent worldwide, meaning speed and personalization have become non-negotiables. If you’re not responding within minutes, chances are the client has already started conversations with someone else.
Most freelancers are forced to choose between speed and quality. Either they send fast, generic pitches or take time crafting personalized messages, but miss the opportunity window. Upprop aims to fix this system.
With automation tools becoming standard across industries, it only makes sense that freelancers adopt smarter workflows. Upprop doesn’t just automate your responses; it makes them better. By analyzing job details and combining them with your pre-saved prompts and portfolio examples, high-quality proposals can be built in under two minutes. That’s not just automation, it’s strategy.
What is Upprop.app?
Upprop.app is an AI-powered Chrome extension built specifically to help freelancers and agencies win more jobs on Upwork. Unlike general writing tools or proposal generators, Upprop focuses solely on Upwork’s ecosystem and the unique workflow challenges it presents. It acts as a real-time assistant that monitors jobs, crafts custom responses, attaches relevant portfolio pieces, and sends everything within minutes of a post going live.
What makes Upprop stand out is its user-controlled design. You use your own OpenAI API key to generate proposals, meaning your data stays local and secure. Nothing is stored on Upprop’s servers, and every proposal can be fine-tuned to match your tone, industry, or niche.
It’s more than just a time-saver; Upprop is a strategic partner in your client acquisition process. It helps reduce the mental load of tracking job posts, writing from scratch, and switching contexts multiple times a day. For freelancers managing multiple services or agencies handling dozens of clients, this level of automation and personalization is not just useful—it’s essential.
AI-Powered Instant Proposals
One of the biggest advantages Upprop offers is the ability to send AI-generated proposals within two minutes of a job being posted. This feature alone dramatically increases your chances of getting noticed. Clients on Upwork often receive dozens of applications, but most hires happen within the first 10–15 submissions. Speed is everything.
Here’s how it works: Upprop continuously monitors Upwork for new listings that match your filters. As soon as a job post appears, it runs that job through your selected prompt (or template) and generates a custom proposal. This isn’t just a fill-in-the-blank reply—it’s contextual, relevant, and personalized based on your skills and portfolio.
You also have the option to review or edit proposals before they’re sent, but you don’t have to. The system is built for full automation when you need it, and manual control when you want it. This flexibility gives you confidence and control without requiring you to sit in front of the screen all day.
Safe, Custom Proposal Generation with Your API Key
Privacy is a growing concern in the age of cloud-based AI tools. Upprop puts your security first by giving you full control over how proposals are generated. You connect your own OpenAI API key, which means all data processing happens locally on your machine. No data is sent to third-party servers, and your proposals are never saved by Upprop.
But it’s not just about safety—it’s about customization. By using your API key, you can fine-tune the proposal writing style to match your tone and voice. Want a more casual approach for creative jobs? Or something formal for enterprise-level clients? All of that is possible.
This also means your prompts can evolve with your brand. As you improve your strategy or gain insight into what works best, you can adjust your prompts accordingly without waiting for feature updates. It’s a flexible system that adapts to your needs and keeps your data secure.
Smart Notifications & Scraping Alerts
Instead of refreshing Upwork every few minutes like it’s a stock ticker, Upprop lets you focus on your work while it monitors new opportunities in the background. With its built-in Upwork scraper, Upprop filters job listings based on your chosen criteria (skills, keywords, hourly rate, etc.) and alerts you instantly.
Notifications are fully customizable. You can choose:
- Slack alerts if you work within a team
- Browser notifications if you’re flying solo
- Webhook integration if you want advanced automation with other tools
This means you’re not just fast you’re precise. You’ll know exactly when the right type of job appears, and you’ll have a smart system responding almost instantly on your behalf. No more lost time. No more missed chances.
Reusable Prompts, Portfolio Matching & Templates
Proposals get better over time when you can reuse what works. Upprop gives you that power. You can save your most successful proposal formats and set them as reusable prompts. For each job, you can either let the AI generate a new response or use a proven template. That means more consistency, less fatigue, and a better win rate.
You can also automatically attach the most relevant portfolio items for each job, ensuring you always put your best work forward. If you manage several services or client types, simply create separate profiles within Upprop. Each profile can have its prompt, portfolio set, and notification rules.
This allows freelancers and agencies to stay laser-focused and professional across every project, no matter how many irons you’ve got in the fire.
Final Thoughts: Automation is No Longer Optional
If you’re still manually refreshing Upwork, writing every proposal by hand, and wondering why growth is so slow, you need to change your approach. The truth is, automation tools like Upprop are giving freelancers a huge edge. They respond faster, stay consistent, and free up time for high-impact tasks.
With its blend of smart AI, real-time scraping, privacy control, and customization, Upprop is more than a tool it’s a partner in your freelance growth.
