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Crafting Winning Bookkeeping Proposals on Freelance Marketplace Sites

The formula for winning bookkeeper proposals (cover letters) on freelance sites

You can absolutely start your bookkeeping business through freelance websites like I did. In fact, I may even be somewhat addicted to the process of submitting proposals and doing discovery calls. And I don’t consider myself sales-y at all. I just genuinely enjoy meeting new people, talking business, and offering a little value—even if they don’t hire me.

So that’s probably the best place to start in this formula. Hopefully by now you know a little bit about how Upwork functions, so I’ll spare the lesson on that. What we’re going to dive into is how to get it to work for you. And as per usual… we’re going to start with—you guessed it—mindset.

Just like we talked about in doing discovery calls, you’ve got to come from a place of service; not desperation. Detach yourself from the outcome. Be ok whether you win them as a client (or in this case you’re shooting for an interview) or not. Then, just be yourself in your writing. Write the way you would speak with a client if you were meeting them on the phone or in person. These days, people value a conversational tone of writing, rather than a formal tone. And think about your market. Companies or entrepreneurs using Upwork typically have a more progressive culture, being that they are already taking advantage of the online technologies of today. Speak directly to them.

“I just genuinely enjoy meeting new people, talking business, and offering a little value—even if they don’t hire me. ”

So once you’ve checked your mindset, you’re ready to start writing your proposal—or cover letter, as Upwork calls it—after we go over a few Don’ts.


  • Recap or attach your resume—the client already has access to your resume (your profile) if you filled it out. Make sure you complete your profile as best you can. I could also go into why providing your resume to potential clients is a no-no, but suffice it to say, they are a client, not your employer. Oblige if they ask, but don’t offer it.

  • Sound desperate—again goes back to mindset… just double check this after you’re done writing your cover letter.

  • Be too wordy—get straight to the point; I’m sure they have a lot of proposals to sift through

  • Copy & paste previous cover letters—I highly recommend tailoring the cover letters to each individual job posting. It really won’t save much time in the end to use a template, but could definitely translate to missed opportunity because you didn’t personalize it enough. Bookkeeping is a position that requires a lot of trust. Being privy to someone’s numbers is intimate. Give them a little extra time to show you care.

  • Skip applying if you don’t meet a minimum qualification—Upwork has something called Job Success Scores and clients can choose to require a certain score. If you are new with your business and new on upwork, don’t avoid applying. Bring it up in your cover letter and just be honest. All of my initial cover letters went something like this: “I see you are requiring a JSS of 80%. I am new to Upwork and working on building my business after leaving the corporate world 2 years ago to raise my kids.” And I still landed those jobs.

Cover letter structure:


Offer a brief greeting and say something to hook them in and show them accountants do have personalities! “Hi there! I’d love to help you out with your monthly bookkeeping needs.” or “Congrats on starting your business! You’re off to a great start hiring a bookkeeper from the get go.”

That first example is actually my go-to. Use it all the time. Of course it varies by the position and their needs, but that’s basically it. Feel free to use it!


Now you can go into details about the position. Here you can talk about how you help similar businesses or entrepreneurs in their field and you enjoy watching and helping them grow.

Or if they’ve explained in their job description a problem they’re having, you can offer a solution (if you know off the top of your head) or how you would go about finding a solution to their issue. Offering a little advice for free shows you know your stuff and shows your value.

Talking details about the job also proves you didn’t copy/paste your cover letter and took the time to craft a thoughtful response to their posting.


Now you can go more in depth about your approach of working with people. Explain that you enjoy working virtually and are comfortable with Zoom meetings and phone communication (which I’m sure is a must for most people on Upwork).

You can even go a little into pricing here, even if you’re unsure still what to price them at. You don’t have to give them a firm price, but you will still need to bid something. Often the accounting jobs are posted as an hourly rate, and I always let them know “I typically charge a flat monthly fee after I’m able to take a peak under the hood and get a good idea of the work involved, so I’ve entered a placeholder for now until we’re able to discuss further.”

Your placeholder could also be your minimum. If you’ve decided you won’t take any clients for under a certain amount per month, mention that. This also adds a little “exclusivity” factor, and they may think, wow, if she’s able to turn away customers, she must really be good!

Many business owners have no idea flat fee is an option or maybe had no idea what to even budget the job at so they just threw a number in there. On the same token, don’t avoid applying to a job because the budget seems way too low. Because it could always be a placeholder.


Once you’ve talked about their needs, the position, and all that stuff they really care about, then you can talk about yourself. You can give your value statement here, where you qualify your prospects: “I help entrepreneurs with their bookkeeping so they can focus on their business and have up to date numbers to make informed decisions.” Keep this super brief; maybe one sentence on your years of experience and the types of clients you’ve worked with (if you have it—otherwise stick with just the value statement). And then move into next steps.


Ask for the meeting. “I’d love to have a video chat with you to see if we’d be a good fit together and get more details about your bookkeeping needs.”

Give them a link to your calendar and website. Make it easy on them to schedule a meeting and to learn more about you.


Sometimes the job description will also have questions they want you to answer. These are screening questions that actually pop up before they see your cover letter. So answer these thoughtfully and thoroughly even if you may have already answered them in your cover letter. I can’t tell you how many times that has happened to me. But alas, I basically re-type my answers. Because they may decide not even to look at your cover letter if you didn’t satisfactorily answer those questions.


This is the time consuming part. Well, actually, I find writing proposals is way less time consuming than the bookkeeping. But do expect to apply to a lot of jobs and maybe get interviews for 30%, and close even less. I think I was usually closing 1 out of every 10 applications. My secret for this, was when I was rocking my little one to sleep, I’f be scouring that day’s job postings and favorite them to come back to later. Often I would just write the cover letter right then and there on my phone. Also in line at school pickup, at the park, anytime I had a few minutes of quiet time to craft my cover letter. Sometimes you just have to squeeze a few minutes here and there for business building activities.


Proposal writing is not an exact science. You’ll continue to tweak and change how you write them as you see what’s working and what isn’t. It’s all about connection. Be human, let the connections happen. Be open to opportunities, and remember the mindset stuff:


  • Come from a place of service

  • Detach yourself from the outcome

  • Be yourself

When you implement these tips, share your wins with me. I want to celebrate with you!

If you are interested in 1:1 support to strengthen your mindset click HERE.


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