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Best Upwork Proposal Strategy for 2026: Land More Clients with ChatGPT! — Transcript

by Emily | Smartsheet Freelance Expert · 3,660 words · 504 segments · language en · Watch on YouTube

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0:00this is the best upward proposal
0:01strategy I will show you my exact
0:03framework and I'll show you how to
0:05leverage Chachi BT to make this the
0:06easiest process ever this video we're
0:08going to talk through what are upward
0:10connects the type of upwork profile to
0:12set up/ membership then I'm going to
0:14talk through the jobs to Target so
0:17there's specific jobs that you should be
0:18targeting when you first start out as a
0:20freelancer and by not choosing the
0:22correct jobs you're basically wasting
0:23connexs and wasting money and I'm going
0:25to share the exact framework that I use
0:27to send winning cover letters and then
0:28I'm also going to show you how I utilize
0:30chat gbt to send winning cover letters
0:33so that you can spend less energy spend
0:35less time drafting up these cover
0:37letters utilize AI to help you do that
0:40what are uper connects we're going to
0:41start with the basics here think of
0:43upward connects as tokens essentially so
0:45they're currency on the upwork platform
0:48that you can use to do different things
0:49on the platform so the biggest thing is
0:51to apply to job so you need connects to
0:53apply to jobs on the platform you can
0:56also use connects to boost your profile
0:58and also set your availability badge if
1:01I was just starting out I would only
1:03focus using my connects on applying to
1:05jobs you can honestly worry about those
1:07other things later down the road but
1:09right now you just want to get that
1:10first job okay so how do you get
1:12connects so technically connects are 15
1:15cents each and they are sold in bundles
1:16I will tell you exactly how many
1:18connects I think you need to start you
1:20can also get free connects from upwork
1:22when you win an interview so this is
1:24kind of a reward for winning that
1:25interview and Landing that client on
1:26upwork upwork also issues refunds for
1:29connects if certain things don't work
1:30out so if you win an interview and then
1:32the client doesn't end up doing work on
1:34upw workk you could get a refund so just
1:36look at the terms of service on upwork
1:38to understand when a refund should be
1:40issued the number of connects for a job
1:41can vary depending on a few factors so
1:44the first one is the job price so the
1:46higher the rate or the higher the budget
1:49for the job the more connects you are
1:51going to need to apply to that job the
1:53next thing is going to be the client
1:55history so if the client has a long
1:57history of working on upwork upwork is
1:59going to require you more connects to
2:01apply to that job as well based on the
2:03competition and number of proposals
2:05expected upward can also increase the
2:07proposals at the end of the day if you
2:09are seeing a lot of connects to apply to
2:11a job it means it's very competitive and
2:13it's probably a really good job when I
2:15was first starting out I did not
2:17necessarily apply to these types of jobs
2:19and I will talk about exactly what jobs
2:21you should be targeting but just
2:23understand that is how they're
2:24calculating the number of connects to
2:27apply to this job now how many connects
2:29do you need that's going to depend
2:30entirely on your personal budget I think
2:32if I was first starting out I would
2:34apply to maybe five jobs per week again
2:37depending on your budget if you want to
2:38speed things up obviously apply to more
2:41jobs if you're sending out five
2:43proposals per week and you need an
2:45average of 12 connects per proposal then
2:47you're going to need 60 connects per
2:49week which equals about $9 plus tax per
2:54week so think of what your budget is and
2:57think of how aggressively you want to
2:59attack getting your first client or
3:01building a portfolio and Vary your
3:03budget based on that but I think the
3:05best strategy for budgeting and
3:07maximizing your connects to the fullest
3:09is truly going to be applying to the
3:11correct types of jobs and looking for a
3:13few key indicators to make sure that
3:15you're applying to the right ones for
3:17beginners I highly recommend looking for
3:21shortterm jobs quick easy fast jobs no
3:25matter the price even if it's like $10
3:28take that job because when you're first
3:30building your profile you want to get
3:32reviews as quickly as you can that is
3:35going to help you out in the long term
3:37if you get a job you land a job on
3:39upwork and it takes 6 months to finish
3:42that is 6 months that you're going to
3:44wait to get a review so I highly
3:46recommend getting the fast jobs you can
3:49look at the duration of the project and
3:51targeting those first and foremost for
3:54utilizing your connects to the max so
3:56some other key indicators to look at
3:58when you are applying to job on upwork
4:01are the activity on this job this is
4:04huge this is very easily missed by new
4:07beginner Freelancers so first and
4:09foremost you want to make sure that
4:10there are less than 15 proposals on the
4:13job currently if there's more than that
4:15if you are a new freelancer with no
4:17reviews the chances are slim the chances
4:20are super duper slim so just keep that
4:22in mind I'm not saying don't apply to it
4:25but if you're trying to utilize your
4:27connects efficiently I would not NE
4:29necessarily apply to that job all right
4:31let's scroll down to look at the
4:34activity on this actual job so you're
4:36going to click the job that you're
4:37interested in this project length is 1
4:40to 3 months if I was just starting out I
4:43wouldn't probably do that I'd probably
4:45look for one even shorter so that's just
4:48my
4:49opinion then if you want to look at
4:52activity on this job this major key
4:54alert
4:55here shout out DJ CID um activity on
4:59this job proposals less than five so
5:03this is really good from a competition
5:05standpoint not a lot of people have
5:07actually apply to this and really the
5:09key to being the first 15 people to send
5:12a proposal on that job is making sure
5:15that you are checking the job feed with
5:17the type of jobs that you're looking for
5:19so I highly recommend doing the save
5:21search feature on upwork here are my
5:23save searches that I have and just to
5:26save a search here let's just do a VA
5:29one
5:30click okay then you can just click save
5:32search save it okay it's been saved now
5:36when I go home boom I can just toggle
5:40between my different save searches makes
5:42it super easy you can check it I was
5:44just scrolling on my phone and checking
5:46my save searches like honestly every day
5:49every morning is kind of when I would
5:51check it around 10:00 a.m. and I didn't
5:53have any problems being one of the first
5:55people to see or apply to a job so I
5:58just recommend doing that that when
5:59you're first starting out we don't need
6:01to be spending a lot of money on this
6:02the next thing to look at on the
6:04activity on this job is to look at when
6:06the client last viewed the proposal if
6:09the client last viewed it within the
6:10last 7 days you're probably good if it's
6:13been more than a week I would hesitate a
6:16little bit because they might be
6:18interviewing people they might be
6:20further down the line they might have
6:21already actually found somebody and they
6:24just haven't taken the job down yet so I
6:27would definitely be a little bit
6:28hesitant if it's over 30 days just don't
6:30even waste your time I would definitely
6:33if the client hasn't looked at it within
6:34the last 30 days don't even waste your
6:36time on that but if it's within 7 to 10
6:39days then I think it could still
6:41probably be active and that's a good
6:42indicator that you should apply to that
6:45job if we scroll down this one shows
6:48this client last you it 28 seconds ago
6:51and they have less than five proposals
6:53three invites have been sent so they're
6:55obviously looking at people's profiles
6:57and sending invites but I would jump on
7:00this if I was a virtual assistant be
7:03like hey you could get in their inbox
7:05and say I'm available today to talk I
7:08bet you would get it these are the five
7:11key items that you need to set up their
7:13framework for your upwork cover letter
7:15so the first thing is to make the first
7:18two sentences of your cover letter count
7:21because when they're scrolling through
7:22proposals of all these different
7:24Freelancers they see only the first two
7:27sentences so you're going to want to
7:28make sure that this is catching their
7:30attention a way to do this is to one
7:33include the client name name what's his
7:35name I got nothing on a name come on
7:38baby what's the
7:40name so look through click through to
7:43the work history see if you can find
7:45their name in previous reviews or
7:47something and then say hello so and so
7:50people are so simple people want to see
7:52their name they're naturally attracted
7:54to their name so if you can include that
7:56you're probably already ahead of the
7:58game and head of a lot of other
8:00Freelancers scroll down to the client
8:03recent history if they have a lot of
8:05history chances are their name may be in
8:08here so see this guy's name is David so
8:11look here's another David so in my
8:14proposal to this person I'd say hi David
8:16another thing that I want to call out
8:18too that I don't hear a lot of people
8:19talking about is using results driven
8:23language within those first two
8:25sentences so what I mean by that is
8:27saying that I improved a process by 50%
8:30for another client that was a similar
8:32project so using language that shows
8:35results within the first two sentences
8:38how are you going to deliver them
8:40results I think that's huge because they
8:42don't want to read a lot they just want
8:44to find that person that's going to get
8:46their result the fastest so if you can
8:49say something along those lines within
8:51the first two sentences that is going to
8:53set you apart from the crowd another key
8:55part of this framework is to make sure
8:57you are reiterating and mirror ing the
9:00same language from the job description
9:03into your cover letter so if they're
9:06using certain lingo you're going to want
9:08to mirror that lingo if they say kpis
9:10you're going to want to say kpis you're
9:12going to want to mention that we love a
9:14buzzword okay like you're going to want
9:16to mirror their buzzwords back to them
9:18because one that's telling them that you
9:20actually read the job description and
9:22then two it means you understand them
9:25the next key part of this framework
9:26which is probably the biggest part I
9:28would say is including portfolio
9:31examples that show you've done something
9:34similar so you understand their problem
9:36and can help them actually solve their
9:38problem and then giving them results
9:41with those portfolio examples so not
9:44only do you want to showcase the project
9:46that you did for maybe another client
9:48but you also want to highlight the
9:50results again being quantitative is
9:53really more powerful than being like hey
9:55I made a dashboard versus saying hey I
9:58made a dashboard that that made this 50%
10:01more efficient or something like that so
10:04keep thinking quantitatively and maybe
10:06you have to like come up with some
10:07numbers as long as you can back up those
10:09numbers feel good about it but it's
10:12really good to actually look at the
10:13projects that you've done and come up
10:15with quantitative results that's just an
10:17exercise that you're going to need to do
10:19anyway so I would recommend doing that
10:21and making sure that you have that ready
10:23for all of these proposals another way
10:26to be super extra about it which I
10:28highly recommend is making a little loom
10:30video putting your face in there being
10:32like hey like here's the cool project
10:35that I worked on that like saved like
10:3750% of people's times and like made
10:40everybody amazing and also here's my
10:42face so that you're not scared to talk
10:44to me cuz I'm a real person I'm not a
10:46robot and making it less than 30 seconds
10:49don't make it long make it like less
10:51than a minute probably 30 seconds cuz
10:53nobody has a long attention span but I
10:56think that's even better than including
10:58profile highlight or portfolio
11:00highlights from your upwork profile CU
11:02they'll have to click through and then
11:04they'll have to think okay does this
11:05really is this really solving my problem
11:08versus if you have a loom video that you
11:10can just paste in there one make sure
11:13that you're not putting any kind of
11:15contact information in there like your
11:17email or anything because that's against
11:19upw Works terms of service so do not do
11:22that but having a video where you can
11:24explain like the process with your face
11:28chef's kiss like that's the best thing
11:30you could probably ever do the last
11:32thing the call to action I see a lot of
11:34other people like freelance people talk
11:37about this but they're not as specific
11:40on this last item so you want a call to
11:43action basically you just want to say
11:45book a time with me but also on top of
11:49that tell them your availability and if
11:51you can make it like ASAP the faster you
11:54can get in front of them the more likely
11:57your chances are of Landing that job so
11:59I would say hey book a time if you want
12:03let's set up a 10-minute call I'm
12:05available today from this time or
12:07tomorrow from this time or the next day
12:09from this time so if you give them those
12:11time slots and you're one of the first
12:13people that they're able to meet with
12:15that's just going to increase your
12:16chances by a landslide basically so try
12:19to put actual times that you're
12:21available if you want to manually set up
12:23this framework and plug in the details
12:24yourself I'm going to show you a
12:26specific example with that framework
12:28broke down so you can just plug and play
12:30with this I'll also include an example
12:33if you use chbt and want to really
12:36streamline this process so first let's
12:38go through the physical example with the
12:41framework that I've outlined so first we
12:43have hello John so you've got the name
12:46there then we want to make the first two
12:47sentences the most impactful with a
12:50results driven statement in there so I
12:52have I've helped automated processes
12:55cutting manual work by 50% we have a
12:57quantitative juicy number number in
12:59there that is eye-catching then the
13:01fourth part of this framework is the
13:03portfolio example or examples if you
13:06have multiple then finally creating a
13:08call to action with specific bookable
13:11time slots like don't just say book a
13:14call with me tell them when you're free
13:16because you're just giving them an extra
13:17step if you're like book a call with me
13:19but guess at my schedule no like give
13:21them your exact schedule at least a few
13:24days out so that it's easier for them to
13:27just reply okay you know three 3 p.m.
13:29Tuesday works for me versus saying what
13:32times are you available okay then it's
13:33just dragging along so make sure that
13:35you're giving them specific time slots
13:37it's so easy to do but also so easy to
13:39forget I think some people might come at
13:41me for telling you to use chat gbt to
13:44send a proposal but to the people who
13:48are skeptical you're just using chat GPT
13:51wrong and I am going to show you ex
13:53exactly how to use it and the exact
13:55prompts that I am giving chat PT to to
13:59make a winning proposal and I actually
14:01utilize obviously the framework that we
14:03just talked about and I utilize that
14:06framework and then I also molded the
14:09prompts for chat PT to keep it in line
14:12like get the Emojis out of there um so
14:14it's not as obvious but it's taking less
14:17brain power for you it's taking less
14:19energy it's maybe sounding a little bit
14:21more professional like in my case I use
14:23chat PT for a lot because if I am going
14:27to be doing a lot I don't have the brain
14:29power to be like crossing my te's and
14:32dotting my eyes right so let that do the
14:34leg work for you so this is my baby this
14:37is my upward cover letter template
14:38generator so I'm going to walk you
14:40through this essentially what you're
14:41going to do is you're going to paste
14:43things into the yellow sections of this
14:46template everything else you don't
14:48really need to worry about so from the
14:51top we have paste job description from
14:54upwork here so you would basically pull
14:57in this job description from the upwork
15:01profile copy it and you will paste it
15:05right here where this is and I'll show
15:07you an example but I'm going to just
15:08walk you through this template first in
15:11this template generator the next thing
15:14it has is this job analysis so this is
15:17telling chat gbt to analyze this job
15:19based on these different requirements
15:22here is my relevant experience so this
15:25is where you will put in your personal
15:27work experience so portfolio examples
15:30feel free to include more than three in
15:33fact please include more than three put
15:35all of your portfolio examples here and
15:37then we'll let chat GPT do the work of
15:40choosing which examples to include in
15:43the cover letter you can also include
15:45any skills or
15:47certifications any industry experience
15:50so I just listed the industries that
15:52I've worked in and then separated it
15:53with a comma and then list your
15:56availability and just make sure that
15:58this is accurate and up to date when
16:00you're generating this via chat GPT down
16:03here is the cover letter format so this
16:06is actually what we're telling chaty BT
16:10how to format the cover letter so we
16:12have the client name opening paragraph
16:16second paragraph third paragraph with
16:17some details in here and then at the end
16:20that call to action let's schedule a
16:2210minute call and then tips for
16:26customization so this is telling chaty
16:28BT like these are your guard rails like
16:31fall Within These guard rails and if you
16:34are running this prompt through chaty BT
16:38and you don't like something that it's
16:39doing like for example I did not like
16:42when chaty BT puts like emojis or icons
16:46in this cover letter so I told it don't
16:48put any of that in there like stop with
16:50that that's like a really big red flag
16:53that I'm using chbt so I said get that
16:55out of here so as you're using this
16:57prompt or generator you can just keep
17:00adding bullet points if you're like oh
17:02we need to tweak this so this doesn't
17:03happen next time so just put it here and
17:06then it will fine-tune this whole
17:08process for you and then here I just had
17:10examples of result Focus statements so
17:12I'm telling chat gbt focus on results
17:15and then this again is just the final
17:16prompt so what this looks like for
17:19me is let's just
17:21say I copy
17:25this and I had a different one here but
17:27I'll just paste it in here so paste that
17:29into here so this is that whole
17:32prompt
17:34and so I had the job analysis we didn't
17:37touch that this is where I put my
17:40relevant experience so I pasted it in
17:43here if you have Loom videos for your
17:46different
17:47projects then you could put the loom
17:49video link within here as well but you
17:53can see I filled it out I filled out my
17:55certifications my industry experience my
17:58availability all filled out then all I
18:01need to do is I'm going to a contrl
18:06c and then I'm going to open chat GPT up
18:08and plug this
18:10in all right and now cat GPT is working
18:13on creating this cover letter for me I
18:16will take this this is going to get me
18:1995% of the way there I might even say
18:22make this more concise I always feel
18:24like the first time that I run this it's
18:27a little wordy so want it to be even
18:29more
18:30concise and then it'll really pair it
18:33down for me so I highly recommend
18:35leveraging chat GPT to write your cover
18:37letter save you time save you brain
18:39energy but you can also always refer to
18:42that other blueprint that I gave you and
18:45manually put those inputs in there if
18:47that works best for you I hope this was
18:49super helpful if it was please like And
18:51subscribe and comment proposal down
18:53below and I will include a link to the
18:56chat GPT prompt that I used to create my
18:59proposals if you're interested in my
19:01journey from corporate engineering to
19:03becoming a sixf fig full-time freelancer
19:06I highly recommend checking out this
19:08next video it goes through my whole
19:10story and some key tips for new beginner
19:12Freelancers if you're interested in
19:14learning more about my freelance Journey
19:17or just freelance tips in general I am
19:19also on other social medias such as
19:21Instagram and Tik Tok so check out those
19:23links below

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