Go through this guide to learn how I built a fully
automated outbound system using Upwork.
Follow each step one at a time, and only move
onto the next phase once you’ve finished the
previous one.
Written by: Nico Hessel
PHASE 01:
Creating an Upwork Profile
(This should take 1 - 2 days)
STEP 1 - THE BASICS
- Create a freelancer account (even if you’re associated with a company).
- You need a professional-looking headshot.
- If you don’t have one, take a picture and clean it up
using [Link]
- Your title should only contain 1 subject.
- My profile says “Social Media Marketing”.
- M
y company provides Social Media Management and
Paid Ads on Meta.
- W
hile you can offer multiple services on Upwork,
your title should focus on one subject.
- Write a detailed introduction (mine is 1700 characters).
- Introduce yourself and your team (if you have one).
-D
iscuss your experience with past clients, provide social proof, and
address the common pain points of your target audience.
-H
ighlight the unique aspects of your company, and include any
special offers or guarantees.
-B
reak the paragraphs up. The introduction should be easy to
read and unintimidating.
- You can see mine here:
2
3
STEP 2 - VIDEO INTRODUCTION
- Film a video introducing yourself and discussing your experience.
- Navigate to the Video Introduction Section on your profile (on the left side)
and click the + button to upload your video.
- This is an opportunity to build trust with potential clients.
- You have 2 options for filming:
- D
irect to Camera: Speak directly to the camera to introduce yourself and
discuss your experience.
- S
creen Record: Briefly introduce yourself, then showcase client results,
case studies, or samples of your work.
- W
hichever method you choose, ensure you have a professional
background and present yourself in a professional manner.
-Y
ou can view my video introduction here: [Link]
watch?v=5mWyan8EQxA
- M
y video introduction has been edited and carefully put together. I want
to emphasize that this is not necessary. A video of you speaking directly to
the camera will work just as well.
4
STEP 3 - PROVIDING SOCIAL PROOF
- R
equest testimonials from any current or former clients to fill out the
Testimonials Section.
-N
avigate to the Testimonials Section on your profile and click the + button to
initiate a testimonial request.
- You’ll see this screen, where you can request a testimonial:
5
- Fill out your Portfolio.
-N
avigate to the Portfolio Section on your profile (underneath the Work History
Section) and click the + button to add a portfolio project.
- Create at least 3 projects.
- Mine are Graphic Design, Facebook Ads, and a Video Testimonial.
- If you put a video testimonial in your Upwork portfolio, make
sure it is in one of the first 3 projects so it is immediately visible
to visitors.
- If you provide a service that is difficult to showcase in an
Upwork Portfolio, such as Bookkeeping, A.I. Automation, or
Cold Email, I recommend showcasing your results. Show
off client testimonials, statistical improvements or a video
walkthrough of your work and processes.
- If you don’t have any clients, or examples of past work, create a mock project
and display it in this section.
Note: Both a portfolio and testimonials are crucial when you’re starting out on
Upwork. The most common objection to work with a new account is lack of
trust. Having a portfolio and testimonials helps build trust, and overcome this
objection.
6
STEP 4 - SKILLS AND EXPERIENCE
- Fill in the Skills Section accordingly.
-N
avigate to the Skills Section on your profile (underneath the Portfolio Section)
and click the pencil icon to enter your skills.
- Fill in the Certifications Section accordingly.
-N
avigate to the Certifications Section on your profile (above the Employment
and Experience sections) and click the + button to upload a certification.
- Y
ou can import these from Credly or add them manually.
- Complete the Employment and Experience sections.
- This doesn’t require excessive detail, simply include all relevant experience.
- This is your opportunity to brag in a professional manner.
- You can see mine here:
7
PHASE 02
Providing Value on a Small Level
(Stay in this phase until you have 2 - 3 jobs and a few good reviews)
STEP 1 - SEARCH CRITERIA
- First, you need to craft a list of search terms.
-U
pwork’s search engine is terrible. You’ll get completely different results
when searching closely related terms.
-G
o to the search bar on the Upwork homepage. Begin searching for all services
that you provide and tools that you use. Then, write down which search terms
provide jobs that best fit your services.
- Y
ou can see my list of search terms here:
8
STEP 2 - CREATING THE TEMPLATE
- Now you need to create a template to submit proposals.
-W
hile each proposal needs to be personalized, having a template for the
structure can be beneficial.
- H
ere is a good template for beginners on Upwork:
Hey {First Name}, I’ve read your job description and I’m confident that I can help you
{insert the goal of the Job Poster}.
Although I’m new to Upwork, I’ve been working in {x} industry for {x} years and I’ve
completed many {insert job type}. {Provide social proof, then outline how you can
solve their problems}.
My portfolio can be found on my profile (below the Work History Section) as Upwork
no longer allows links in cover letters.
I’d love to hop on a call and hear more about your project. Is there a time this week or
next that you’d be free for 15 minutes?
Thanks,
{Name}
Note: Everything inside the brackets needs to be personalized.
- This loom video will teach you how to find the Job Poster’s first name:
[Link]
cb385-c2b8-4f97-97bc-920d65dd1098
9
- It is critical that you check for the Job Poster’s name. On their screen, only the
first 300 characters of each proposal are visible in the preview. “Hey Nico” grabs
my attention far more than “Hey”.
- The only links Upwork allows in proposals are google drive links.
- If you provide a service that cannot be showcased in the Portfolio Section
of Upwork, put all your work into a google drive folder, and attach the link
to your proposals.
- If you do this, you’ll need to change the third paragraph in the
proposal template.
10
STEP 3 - SUBMITTING PROPOSALS TO SMALL JOBS
- M
y first 2 jobs were each priced at $60, and I spent over 4 hours
fulfilling each one.
-W
hile this wasn’t ideal, having those 2 reviews was the reason my third client
booked a meeting with me. That client payed me more than $6,000 over the
next few months.
- Start by submitting proposals to small jobs that you can easily fulfill.
- Search for fixed-price jobs under $100 .
- M
ake sure you are only searching within your country.
- Bid the same price as the Job Poster’s budget for all fixed-price jobs.
11
-O
nce you’ve applied to all relevant fixed-price jobs under $100, search for hourly
jobs paying between $10 and $20 per hour.
- For hourly jobs, bid within the range the Job Poster provides.
- Y
ou don’t need to worry about boosting your proposals in this stage as most small jobs
don’t get more than 20 applicants, depending on the country and industry you are
searching in.
12
STEP 4 - SELLING ON UPWORK
- Selling to prospects on Upwork is incredibly easy.
-T
he prospect has already admitted that they need your service. You just have to
prove you’re the right person for the job.
- O
nce you have case studies, video testimonials and reviews this becomes
even easier.
- Y
ou can get my Upwork Sales Guide here: [Link]
d/16Qoy9Gjz3QXoI3Qd6Nbe_-RLg44IGUM-5e2kSFJeFUM/edit?usp=sharing
Note: It’s important to be flexible. Sometimes the prospects have dozens of
questions prepared. Go with the flow, but make sure you have a chance to pitch
your service.
Note: When you complete a job on Upwork, make sure the client leaves you a great
review.
13
STEP 5 - PLATFORM GUIDELINES
- Process all payment on Upwork.
- J ob Posters can view the amount of money you’ve earned, which builds trust
as your earnings increase. Additionally, clients can only leave a review for you if
the payment was processed on Upwork.
- Keep all communication on Upwork.
-U
pwork does not allow you to communicate with your prospect outside of
the platform until you both have signed a contract on upwork. If you take the
conversation off Upwork, your account could be flagged and suspended.
- S
ome jobs will require you to answer custom questions along with your
proposal.
- I generally write 2 - 5 sentences for each question.
- You can see an example of those questions here:
14
PHASE 03
Submit Hyper-Personalized Proposals
(Stay in this phase until you have earned $7,000 and have at least 5 good reviews)
STEP 1 - UPDATING THE JOB CRITERIA
- Now it’s time to submit proposals to higher quality jobs.
- F
irst, you need to identify the job posts that give you the best chance of being
hired.
- Here is the checklist I use:
- P
ayment verified or specific information about the company in the
description.
- Looking for a freelancer in your country only.
- L
ooking for a service that you can provide.
- Less than 50 proposals submitted (the fewer, the better).
- T
he bidding range for fixed-price jobs includes $500 or more. (In phase 3,
you can apply to larger jobs. $500 is my minimum, but the exact price is
your choice.)
- The bidding range for hourly jobs includes rates of $15 or more.
- This may sound low, but sometimes people think a project will take
8 hours, and they are ready to pay $120. However, in reality it will only
take you 2 hours.
Note: Rarely will there be jobs that fit all of these criteria. If the first 3 are met,
you can apply.
Note: You will have the best chance of signing a client when searching within
your own country. However, if the jobs in your country tend to be less financially
rewarding, you may want to consider testing other locations in your search. When I
search for jobs outside the U.S., I filter my search to intermediate and expert mode
only.
15
STEP 2 - SUBMITTING PROPOSALS
- N
ow that you have updated your job criteria, you can begin submitting
hyper-personalized proposals.
- Use the template from Phase 2.
- Here is an example of a proposal that led to a job offer for one of my clients.
ote: Sometimes, Job Posters will request that you put a certain word in your
N
proposal to indicate you read the entire job description. In this case, the word
is “Creative”.
- The personalization in this proposal is extreme.
- It identifies the clients needs and addresses them in the first line.
- It references experience in both of the services the client needs.
- It provides specific examples of work that relate to this job.
16
STEP 3 - BIDDING AND BOOSTING
- When submitting a proposal on Upwork, you are required to include a bid.
- Always select ‘never’ in the rate increase dropdown menu.
17
- B
id within the hourly range provided, and aim to align with the Job Poster’s
average hourly rate paid.
-W
hen you click on a job, a pop-up will appear on the right side of your screen.
Near the bottom of the list is the average hourly rate the Job Poster has paid
other freelancers on Upwork.
18
- Boosting:
- It costs 4 - 16 connects to submit each proposal.
- You can buy 10 connects for $1.50.
-Y
ou have the option to submit the proposal for 8 connects (green button at
the bottom).
-A
dditionally, you can boost your proposal by spending more connects to
appear higher on the Job Poster’s screen. Only 4 spots are available for
boosting.
- This is how it appears on the Job Poster’s screen:
19
- You can see the proposals at the top have been boosted.
-C
onsidering that jobs often attract 50 or more applicants, boosting provides a
significant advantage.
- I recommend bidding 2 connects more than the current first place bidder
(as long as you don’t exceed 25 connects).
- If that is not possible, bid enough to claim the second or third spot in
the rankings.
- The amount of proposals you boost is entirely up to you and your budget.
- For reference, I boost around 60% of my proposals.
20
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STEP 2 - TRAINING A VIRTUAL ASSISTANT
- Now that you have hired a Virtual Assistant, it’s time to train them.
- I dedicate 10 - 15 hours to training.
- I divide it into 4 - 5 calls that each last 2 - 3 hours.
- Y
ou can access my training guide here: [Link]
document/d/1mZr87Ar1gdGQU7_xs2OiucCmG_k6ttSvIDFG_YuLI9k/
edit?usp=sharing
- I start my VAs with 10 hours of work per week.
- I meet with my VA for an hour every weekend to go over all of the proposals
she submitted and address any questions. I recommend you do the same.
- If you want more deal flow, simply increase their hours.
22
STEP 3 - SIMPLIFYING AND SCALING
- O
nce you have $7,000 earned on Upwork and a handful of good reviews, it’s
much more reasonable for someone to trust you.
-A
t this stage, I would recommend using a shorter proposal and directing the
job poster to your Upwork profile.
- Y
ou can see my template here:
Hey {First Name}, I’ve read your job description and I’m confident that my team and I
can help you {insert the goal of the Job Poster}. There’s a reason we have a 100% success
score. It’s because we get the job done right the first time, or we work for free until
you’re happy.
I’d love to hop on a call and hear more about your project. Is there a time this week or
next that you’d be free for 15 minutes?
Thanks,
{Name}
P.S. - We keep our proposals brief as we know you get many of them. But if you check
out our profile you can get an in-depth look at our company, our projects, testimonials,
and reviews.
P.P.S. - If you’re interested in hearing straight from the horse’s mouth, feel free to check
out this video testimonial from {insert name and title of the person who gave you a
video testimonial}.
(This can be found on our profile below the Work History Section, as Upwork no longer
allows links in cover letters.)
Note: If you don’t have a team, you’ll need to tweak the language in this
template. And if your video testimonial is in the form of a google drive link,
simply delete the last line in parenthesis, and attach the link as the last line in
the P.P.S. section.
- Bonus:
- If you offer multiple services, consider grouping your search terms and creating
separate proposal templates for further personalization.
- Y
ou can see an example here: [Link]
3ATESv_DWTX3VfDftTwjnUFktE1mHjlJ9-mwLpmA/edit?usp=sharing
23
STEP 4 - MAINTENANCE
- KPIs and Reporting:
- KPIs:
- Y
ou can see all Upwork KPIs here: [Link]
GTlYJgM2m1nPORtBRS4yPIzwF2-89d9mS5Lf89FXkw/edit?usp=sharing
- Reporting:
- I have my VA fill out this spreadsheet after every shift:
[Link]
qh757CEf7ZqSw2YwNTxD1QBwcbPcio/edit?usp=sharing
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