Crafting a compelling proposal is crucial for winning your first Upwork contract as a freelancer. Your submission must convince potential clients that you are the best fit for the job. Follow these tips to create winning proposals that will impress clients and successfully land jobs.

Carefully Review the Job Posting

Read the client’s full job description and requirements closely before drafting your proposal. Identify key details like:

  • Skill sets or experience requested
  • Deliverables to be produced
  • Preferred timeline and deadlines
  • Budget or rate expectations
  • Any special considerations or instructions

Understanding exactly what the client needs ensures your proposal directly addresses their specifics.

Highlight Your Relevant Skills and Experience

Connect how your background, expertise, and past work equip you to successfully complete this project. For example:

  • I have 5 years experience developing WordPress websites for small businesses like yours.
  • I hold a Master’s degree in graphic design and have designed logos for over 50 clients.
  • I have previously managed social media campaigns with monthly budgets up to $5,000, exceeding targets.

Back up your capabilities with specific facts, achievements, testimonials, and portfolio samples as applicable.

Explain Your Approach

Describe how you would handle the project and key tasks involved. Outline your methodology, tools you use, and typical process to give the client confidence you understand the work.

  • For a content writing job: “To begin research, I utilize surveys, interviews, and aggregated data to deeply understand your industry and target audience.”

Address Their Pain Points

Look for clues in the job posting about problems the client struggles with. Explicitly explain how your skills and plan will solve their issues if hired.

  • For example: “I understand how difficult it can be finding designers who can properly brand your company’s unique voice. My design process starts with identifying your differentiators…”

Provide an Outline and Timeline

Lay out a project timeline with expected milestones and delivery dates based on requirements. This demonstrates you can complete the requested work within their preferred schedule.

  • For example: “If awarded this project, I will deliver wireframes for initial review within 5 business days. Following any revisions, I will then code the full mobile app within 3 weeks.”

Outline Pricing and Payment Expectations

Provide a clear pricing quote or rate offer based on their budget specifications. Explain preferred billing and payment terms – important for avoiding misunderstandings.

  • For example: “My rate for social media management services is $X per month. I offer monthly billing on net-15 terms upon receipt of a signed agreement.”

Close with a Call to Action

Wrap up by thanking the client for considering you, expressing enthusiasm for the project, and urging them to contact you with any other questions.

  • “I’m excited at the prospect of collaborating with you on this logo design. Please let me know if you need any other details to make your hiring decision. I look forward to working with you soon!”

Follow Up Professionally if Not Selected

If the client passes on your proposal, follow up politely asking for any feedback about why they chose another freelancer. Their constructive criticism can help improve future submissions.

Frequently Asked Questions

How long should my Upwork proposals be?

Aim for personalized proposals between 300-600 words. Be succinct but include enough details and customization to show you read and understood the job posting.

What types of information should I avoid including in proposals?

Don’t include any sensitive personal details or request privileged company information early on. Keep the focus on your capabilities and approach.

Is it better to submit generic or highly customized proposals?

Always tailor and customize your proposal extensively based on each individual job post rather than sending a generic template submission.

Should I only bid on jobs where I meet 100% of the required qualifications?

If you meet at least 70-80% of needs, it can be worth applying by highlighting your strongest relevant skills. But focus on great fits.

What are some signs my proposals may need improvement?

Consistently not hearing back from any clients indicates your submissions need polish. Ask clients for feedback on rejections to improve.

Crafting polished, personalized proposals tailored to the client’s needs gives you the best shot at winning great Upwork jobs. Use these tips to showcase your fit and get hired faster.


  • Gio Watts

    Gio Watts brings over 10 years of digital marketing experience to his role as marketing manager at Walletminded. In his current position, Gio oversees brand marketing, campaign management, and audience growth initiatives. Prior to joining Walletminded, Gio held marketing roles at several ecommerce and SaaS startups, most recently serving as senior marketing manager at CloudTable Inc. There, he specialized in paid social advertising and content marketing. Gio holds a bachelor’s degree in business marketing from the University of Oregon. He is a certified content marketing specialist and frequently guest lectures at his alma mater. When he's not devising omni-channel marketing campaigns, you can find Gio coaching youth basketball and indulging his passion for live music.

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