Upwork Cover Letters That Convert
Tired of spending time and Connects on Cover Letter proposals that never get viewed?
Then you you need to try PouncerAI - a new AI tool that generates highly personalized cover letter proposals in seconds. Stop wasting time and start closing more clients with PouncerAI.


Your Competitive Edge on Upwork
Apply To Jobs Faster
Instantly see new Upwork job postings within your Chrome Browser Sidebar so you never miss a new job opportunity!
Powerful Cover Letter Templates
Quickly create cover letters that grab clients attention using the PouncerAI-assisted templates.
Intelligent Chrome Extension
PouncerAI is optimized to work directly within the Upwork interface making it fast & easy to generate a reply!
Hear directly from our users
Risk-Free Guarantee


Power packed features to help you save time on Upwork
Stay Ahead of New Opportunities
With PouncerAI, you’ll see Upwork jobs as soon as they're posted—right while you're actively browsing. Our smart Chrome extension keeps an eye on your saved job searches whenever you're logged into Upwork with your browser open.
As soon as a relevant new opportunity appears, you'll get an instant notification right in your sidebar, letting you apply immediately without switching tabs or losing your workflow.


One Button. One-click. That's it!
The PouncerAI Chrome Extension instantly detects the job details on Upwork, eliminating the need to copy and paste into ChatGPT. So when you are ready to generate a Cover Letter, just click the button and let the AI system create a custom-tailored cover letter for you.
Create Winning Proposals with Easily Customizable Templates
With PouncerAI, you can generate attention-grabbing proposals in seconds. By leveraging your Upwork Profile and the client’s job description, PouncerAI Templates automatically deliver a tailored, persuasive cover letter designed to win clients.
But that’s not all—PouncerAI also lets you create and customize your own AI-driven proposal templates to suit your unique style and needs. Start winning more jobs with less effort today!



Make your Proposals Stand Out with the Upstyler Toolbar
Turn your proposals into eye-catching visual masterpieces with the Upstyler Toolbar. Specially designed for embedding Unicode characters—like bold, italics, bullets, and emojis—this toolbar helps add a touch of flair that will captivate a client's attention and make your cover letter unforgettable.
Get jobs for everyone on your team
PouncerAI makes it easy for you to manage multiple freelancer profiles on Upwork. Just add your freelancer’s profile and then use PouncerAI to send custom-tailored proposals for individual freelancers.
Generate more business for your agency with PouncerAI.



You Are Not Alone
Being a freelancer can be lonely. We know, we’re freelancers ourselves. That is why we created an exclusive community with the resources you need; from how to optimize your Upwork Profile, to weekly mastermind strategy sessions, to a large video library of tips and tactics you can use right now.
Sign up today to get your invitation to our exclusive freelancer community!
Frequently Asked Questions
No. PouncerAI does not require your account information or login credentials. The system works independently of Upwork so you can keep your private information, private.
No. We believe that you should be in total control of what jobs you apply for and what your cover letter proposal should say. There is nothing worse than wasting Connects to apply for jobs that you are not interested in or where your cover letter proposal is inadequate.
Great question. While ChatGPT can write general content, it doesn’t understand Upwork’s algorithm or what actually performs well on the platform. Our tool analyzes your real profile and generates content that’s keyword-optimized, client-focused, and designed to help you show up in more searches and get more invites—not just sound nice.
Yes, Upwork does allow freelancers to use Chrome Extensions with Upwork. For more information please visit https://support.upwork.com/hc/en-us/articles/17652357074451-Guidelines-for-using-Google-Chrome-extensions
You can, but that still leaves you with more questions than answers. Our recommendations are tailored specifically to your profile—so instead of generic tips, you get ready-to-use content that you can confidently copy, paste, and publish. It’s like having an expert write your profile for you, based on what actually works.
No. In fact, it helps Upwork better match you to the clients on the platform. It's a win-win for everyone - better profiles mean better matching, resulting in happier clients. Nothing in our tool or extension violates the TOS from Upwork or will compromise your account status.
Nope! We specialize in helping freelancers around the world communicate more confidently and clearly with Western clients. All our recommendations are written in professional, natural-sounding English—so you can present yourself effectively, even if English isn’t your first language.
This is especially valuable for freelancers in competitive categories like WordPress development, Shopify, SEO, social media management, and design—where hundreds of freelancers might be competing for the same job. Whether you’re just getting started or have years of experience, the Profile Optimizer helps you stand out, rank higher, and position yourself as a top choice for clients.
Upwork does not provide an easy way to add any styling to your cover letters. So we created a tool to help. The Upstyler toolbar makes it easy to add Unicode elements to your Upwork cover letters and proposals. Not only can you add emojis, you can also add Bold and Italic text, along with real bullet points. No other tool provides our unique Upstyler Toolbar!
Your Profile in PouncerAI is different from the one in Upwork. Your PouncerAI profile is specifically designed to work with the AI-prompts we developed to help the AI system know who you are and what you have done. Your Upwork profile is designed for people to read whereas your PouncerAI profile is designed for the AI system to understand.
No, you don’t need to know anything about AI. But if you are interested in learning, or already comfortable with AI, you can use our built-in AI prompts to tailor the output of your proposals.
Yes. We use ChatGPT 4.0 and will continue to improve our system using the latest API versions available from OpenAI.
Yes. While we provide a number of sample prompts in the system, you can create and use your own prompts within PouncerAI. Even better, your prompts can reference the information we store about you and the job you are applying for.
Great question! First and foremost it's about convenience and speed. Instead of copying and pasting information into ChatGPT, PouncerAI has everything about you and the job ready-to-go when when creating a proposal. Second, we provide a number of proven AI prompt templates specifically designed for Upwork so you don't have to spend time instructing OpenAI what you want written. Finally, OpenAI does not have the job information; a key component you will need. We do. So if you are tired of having multiple tabs open and wasting time copy/pasting information, then you will love using PouncerAI.
We take privacy and data security very seriously. While we do store the job information and your proposals in the system, we do not share your proposal information with other users. Further, when you cancel your account, we remove all proposal data, profile information, and templates you created.
Daniel Reiling and Sean Jackson are the creators of PouncerAI and active freelancers on Upwork.
Frustrated by the Upwork platform, they decided to create their own tools to help improve the way they attract potential clients from Upwork.
After showing their internal tools to other freelancer friends (and repeated requests to use them), they decided to make these tools available to any freelancer.
Finding quality work on Upwork can be a challenge, and PouncerAI makes the entire process fast and easy.
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