Serve Scale Soar®

How to Use Upwork to Land Premium Clients - With Ashley Kruse

• Brandi Mowles • Episode 277

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0:00 | 21:59

I've told people for years to stay off Upwork. I've literally never even logged into the platform. But today's guest, Strategist Society member Ashley Cruz, made me eat my words.

Ashley signed her first high-ticket client on Upwork in just 15 days, and seven months later, she was completely waitlisted. Her cost per client? $45. In this episode, she's breaking down exactly how she finds premium, retainer-based clients on a platform most service providers have written off.


In this episode, you'll learn:

  • Why high-ticket clients are actually on Upwork (and why they're not looking for cheap labor)
  • How to pitch retainer rates even when a job posting lists hourly
  • The $45 strategy that turns into $9,200+ in contracts
  • Ashley's 3 steps to get started on Upwork this week
  • Why your Upwork profile should read like a sales page, not a LinkedIn bio

Resources mentioned:


Read the full blog post: https://brandimowles.com/277




Follow the Podcast: https://podcasts.apple.com/us/podcast/serve-scale-soar/id1477998650

Follow Brandi on Instagram: https://www.instagram.com/brandimowles

Follow Brandi on Facebook: https://www.facebook.com/Brandiandcompany

ASHLEY UPWORK

===


[00:00:00] 


Brandi: Welcome. Welcome back to another episode of The Serve Scale. So podcast. I'm beyond excited because today we are talking about a topic I know absolutely nothing about. And I feel like I know a lot about a lot, and this is one of the topics I can be like, I've never even logged into the platform. And so we have a special guest.


She's not only a strategist society member, but she also is helping freelancers land premium clients on Upwork. So Ashley, welcome to the show.


Tell my audience who you are as a person and about your business. 


Ashley: Hey everyone, I am so excited to be here. My name is Ashley Cruz, and first and foremost, I am a done for you service provider. So I am an ad strategist. I've been doing ads now for just over three years, and I absolutely love it. And as of 2025 when I was building out my own roster, I started.


Leveraging the Upwork PLA platform where I started to find a lot of [00:01:00] success and over time I was just like, okay, cool. I wanna teach this. And so I now am also helping freelancers be successful on the Upwork platform, helping them find what Brandy calls champagne clients on a platform that traditionally has a really bad reputation.


Outside of that, though, I am a mom. I am a wife. I am just a regular old gal in the Midwest. Out here just trying to do the Lord's work, with helping people. So that's me. 


Brandi: It's so funny 'cause yes, I do say champagne clients and before Ashley I would've been like, if you want some PBR clients, you go on to Upwork.


And so it's also so funny to me that so many people I don't drink. But I used to, and in college that's what you drank was PBR and people don't know what that is, but it's a really nasty college beer. So we say PBR clients or champagne clients. And and it's so funny 'cause I have a GPT that I created with my knowledge, so it even tells people don't use Upwork, but [00:02:00] Ashley is proof that Upwork can actually land really high premium clients when you know how to work.


The system and the platform. So Ashley, tell me what even made you jump onto Upwork to give it a try? 


Ashley: Yeah, so in 2024 I was back in corporate working a regular sales job, and at the end of 2024 I was like, okay. This is soul sucking. I can't do the sales life anymore. I wanna come back into my business. And so I decided to come back.


But for me, I didn't have a runway. There was no, I didn't have, I think I had one retainer client at the time for ad services, and I was just like, I don't think I have the time or the capacity to wait 90 days or 60 days, or even 30 days to find my next client. Like I needed a client yesterday. And I decided to jump on the Upwork platform and I just started like sending out pitches and I used a process that I used on LinkedIn several years ago when I used to [00:03:00] write resumes. And I come from LinkedIn in general, so I understand the process of hiring and what you know, your potential people that are gonna hire you are looking for.


And so I started using this methodology that I've created and. It went off, right? So I signed my first client from Upwork. That was a high ticket client in the first, I think it was like 15 days that I was on the platform, and then seven months later I was waitlisted. And all of those clients, for the most part, came from Upwork.


I had a few referrals that came in, but. Every day I was working my Upwork leads. And for me, because there was such high buying intent, it made sense for me to spend my time there because I just knew that it was gonna be a lot less of an uphill battle and a lot less convincing energy because these people knew what they wanted.


So seven months it took me to fill out my client roster and I was like, okay, there's something to this process. And I absolutely love it. It feels the [00:04:00] steadiness and the predictability that I've always lacked in my business. And so that's where it came from. 


Brandi: Okay, so for the people who have never even logged onto a work like myself.


How do you know, like how do you go by about finding like clients that will actually pay you a premium rate and aren't looking for ad managers or other service providers that are like $500 a month or $10 an hour, like that's who you're competing against. So how do you find the clients who don't want that but they want the experts?


Ashley: Yeah, I love that question. So I'm gonna be real, there's a lot of crappy jobs on the Upwork platform, but I think that there's a little bit of an art to it. So when you jump into the platform, you're gonna be bombarded with hundreds of jobs, and especially if you're an ad manager or you're an ad strategist, or you're someone that has that like strategic level brain, you're gonna read these opportunities and you're gonna be like, eh, I don't think that this is a great fit for me.


And [00:05:00] then you're gonna see one that is a good fit. And the minute you read it, the budget's gonna be in alignment. The way that they're talking about the results that they want is gonna feel really good for you. And the results that they're asking for are gonna be and seem reasonable based on what we do as service providers.


And so it is a little bit of an art and you have to learn how. Find those opportunities. But a few ways that you can do that is simply just by searching for the types of jobs and getting consistent with looking at jobs so that you know how to discern what's worth your time and what's not. You're gonna, there's gonna be a little bit of trial by fire to be honest.


But once you figure it out, it, it'll work beautifully. 


Brandi: Okay, so correct me if I'm wrong, 'cause once again, ding-dong, don't know anything about Upwork. So if someone is looking for jobs on Upwork, isn't it mostly paid by the hour? 


Ashley: So there's actually both. I think this is a [00:06:00] common misconception. A lot of people do pay by the hour, but actually a lot of clients want that retainer type of service or a project based service, and they'll often say the way that they want to pay in their job description.


For me though, as a strategist, I always say and set that expectation up front that I don't work on an hourly basis. That's just not how I do my work. The level of strategy that I bring to the table is on a retainer rate or on a project by project basis, and I can share more about that with you, during a discovery call or whatever the case might be.


But I think it's as a strategist, it's our job to show up and dictate that conversation because the client just doesn't know, they don't understand. And anyone who's gonna buck back on an hourly versus a retainer rate probably aren't your right fit client anyway. 


Brandi: So are you responding to these job ops even if they do put an hourly rate?


Ashley: Yes, I do. So again, I just am gonna assume that [00:07:00] they don't know what they don't know. Yeah. So I'm gonna say, Hey, like I see that you're doing an hourly rate. This is actually how I work. If that's something that you're open to, let's talk about it. And that works really well for me. Like I get for every 10.


Pitches that I send, I'm getting three, sometimes four responses from people. So it's I think that there's like this misconception that's oh, if you're hourly or if you only want retainer, they're never gonna respond. But in my experience, that has not been the case, and it's because I use case studies, it's because I use my results to get past that.


That's what they care about. They don't care about how you get paid. They care about whether or not you can give them the result they want. 


Brandi: Okay, so speaking of that, then, a lot of people assume that like Upwork's great for people just getting started and you're not someone who's just getting started. So who do you think Upwork is actually perfect for?


Ashley: To be honest, it's perfect for anyone. So it depends on if you're just starting out, it's a great way to get your feet wet. [00:08:00] Like one of the things that I remember when I was first starting my freelance business is I was like, I just want somebody to let me into their ad manager so that I can play around and see how it goes.


Those types of jobs are on Upwork. But now as an established service provider, there's also people who are spending over a hundred thousand dollars a month on Upwork and they just are on ads rather. And they just don't know where to find the right talent. And they don't wanna post a job on LinkedIn because it costs money.


They don't wanna post a job on other websites again, 'cause it costs money. Upwork is free for them to post, and they're gonna get a solid number of people that. Are gonna come in with that right experience. They get to be a little bit picky about who they choose. And so as long as you're coming in with that experience, you could get a job if you have lots of experience and you could get a job if you don't have a lot of experience, there's a client out there for everybody.


Brandi: And I think that's a good thing to note and like a reframe is that a lot of people, like we just assume that people know how to find. Service [00:09:00] providers, but that's not the case. It's like people actually don't know where to look for service providers, this comes up a lot. That's why we have so many people at DEM US and they're like, Brittany, I need an ad manager.


Where do I find one? And I'm like, Hey, we have a directory for that. But when before we had a directory, I said, you can gimme a post and I'll post it in my group. But most of the people don't know where to get service providers and a platform like Upwork. They spend money on advertising. Their ads are in podcast, they're on Hulu.


They pop up on my peacock, like wherever I'm watching, there are those ads. And so when people see that, they're like, oh, that's where I go to get talent, because that's what the ad told me to do. And so I think that's a really good reframe of this isn't just for people who are looking for cheap labor.


It's people who are just looking for labor and they don't know where to go. So going back to the fact that you said, they don't have to pay to be on the platform. Do you have to pay to be on the platform as the [00:10:00] freelancer? 


Ashley: That is a great question. The answer is no. You don't have to pay. There are benefits to paying to be on the platform, so there's a couple of things you can do.


You can get a badge. I don't have a badge that I pay for. You earn badges through like consistency and pitching, but you don't have to pay for those. The thing that I do pay for, and the thing that I recommend people pay for is the Connects. The Connects are what help you rank higher. When you're sending a bid or when you're sending a pitch to your potential client.


So for me, when I know that I can absolutely crush the results they're looking for, and I'm a really good fit, or I have a case study that literally speaks to exactly what they're looking for, I will use my Connects to get myself in a higher place so that they actually see who I am. What I bring to the table.


I don't do that for every single pitch, but you use those connects to get yourself seen. It's very similar to how you can rank in Google for, different searches. You're [00:11:00] just paying for placement at that point. So if you have, a high intent buyer, that's a good fit for your work.


Using those connects to get yourself seen is a good, is a good strategy. 


Brandi: Have you ever tracked, like in a 90 day span, or maybe, like last year's number, how much you spend to get, when I spend X amount of dollars, this is how a client. 


Ashley: Yeah, it's a great question. For me. That number is 300 Connects, which equates to about $45 in Connect spend.


So for every $45 that I spend, I am making my retainer rate, which is. 2300 times four. 


Brandi: Oh yeah. 


Ashley: So it's a pretty good ROII 


Brandi: think that's the thing that people like get in their head, but as a service provider, you are you either paying in time or you're paying in money to find clients. For me, when I was back in MLM, I would pay a ton of money every single month for an email and phone list.


That I would have to pick up [00:12:00] and dial the numbers for you. You're spending it on connect. Some people choose to spend it ad dollars on meta. Some people choose to spend ad dollars on LinkedIn or wherever it is, but if you're not spending dollars, you're spending time. And for some people it's more worth it to spend dollars than time.


Yeah. And so it's the same thing with clients when they come and they're like. I only do organic, and I'm like, great. I only do ads because I value my time. And that's not true. I do both, but I just like that whole concept you're either paying for with time or money. And so with you, you're leveraging money and it's not even that much.


$45 for $2,300 contract and then they stay four months. But then, so my question is, does Upwork take a percentage of the contract? 


Ashley: They do, they take 10%. So what I always recommend people do is that you adjust your pricing accordingly, right? And your [00:13:00] leads or the people that are on the other side trying to hire you, they understand that.


And in my experience, I've had clients who have stayed with me for eight, nine months and they don't mind being on the Upwork platform, but they tell me like, Hey, let me know if we need to adjust pricing to account for what Upwork is taking. And again, like that's. Part of the approach is like when you are able to discern the right type of champagne client, you can tell and you sense that they actually care not only about their results, but like you as the team member.


Those kinds of things open up very easily and they are so willing to work with you. And I just, I love that because it's five clients that I've had over the last five years or last year wouldn't have found me if it wasn't for Upwork and like they're some of my favorite people to work with. 


Brandi: So then my question is, and this may be of a dirty question is, and not that type of dirty y'all, but like we're like doing some shady stuff.


Dirty is, do you take them off the [00:14:00] platform? 


Ashley: Okay. This is a question that I get a lot and I will never suggest somebody take someone off the platform because if you get caught. You could get your profile band. That's just the truth of it. And I wouldn't want any, I wouldn't want that to happen to anybody, but there's also keeping them on the platform can be helpful because.


You're protected that way. So if somebody walks away, again, you don't know this person. If somebody tries to bow out of their contract, if somebody doesn't pay, Upwork has ways to manage that so that you mitigate risk that you might not see. 


Brandi: Okay, so someone's listening to this and they're like, okay, Ashley, you've sold me on it. I'm gonna jump on the platform. What are the like three top three action steps that they could do this week? 


Ashley: So first and foremost, create your profile. I would say that's like the number one thing.


And don't copy and paste whatever you put on LinkedIn into your Upwork profile. I want you to think of your [00:15:00] Upwork profile as a sales page, right? Like it should feel very similar to your Work With Me page or whatever website that you use to promote your services. Use your case studies as part of your profile.


And that's the second suggestion that I have is. Get a case study and find opportunities that really relate back to the case study that you're creating, right? The more that your ideal client can see that you have the experience that they're looking for, the more likely they are to pay premium rates.


So if you're just. Posting or if you're just pushing out a generic proposal and you're not taking any time to show them why you're the best fit they're gonna treat you like a commodity. And when someone treats you like a commodity, it's because they think that. They can find what you do somewhere cheaper.


And the goal of this is to not do that. You're not trying to send a bunch of pitches. You're being very specific with who you're pitching to and your profile, as well as your case study, help to bolster that [00:16:00] rate that you're gonna charge. So those are the first two things. And then the third thing I would say is start sending pitches.


Like just start sending 10 pitches. Make it your goal. I always like laugh because I follow Brandy's methodology with 30 minutes of marketing minutes every single day, and I tell people. Okay, take one of your marketing minutes for the week and send out five to 10 Upwork Pro proposals. Okay?


Track how many you send, see what your view rates are, see what your response rates are, and see if they led to any calls. That will tell you where you need to focus your time and energy is your pitch to vague is, are you not being direct enough and getting someone to a call? Those will tell, those numbers will tell you what to do, but that can't happen unless you're consistently.


Showing up and pitching. 


Brandi: Ah, I love it. Okay, Ashley, this has been so good. Maybe in another day, in another life, I would've been on Upwork, but I think this is great [00:17:00] for people to try. I really do. I think it is something that like if your people are on there, if you wanna give it a shot. Then go do the dang thing, give it a shot for 90 days.


Decide how much money you're willing to invest and do that. But also, I know because Ashley is one of our strategist society members and we've been working on this together, she has a resource for you. That you can go and learn more how to do this. So you can either go off now and do it on your own, or you can join Ashley in her training and learn how she's been able to do this with the step-by-step process.


Ashley, will you tell us more about what you got for my listeners? 


Ashley: Yes. So if you are brand new to Upwork and you are just trying to figure out like what you should be on your profile, the first resource that I just wanna offer you, it's free. It's my Upwork profile checklist. You can grab that checklist.


It goes through eight different parts of your Upwork profile that you want to have dialed in. So that one. You can feel like you know what you're doing on the platform. And then [00:18:00] two, so that you can be found by other people who are searching. 'cause that's one thing we didn't talk about today guys, is that it is a massive service provider directory.


So people can literally search for you based on what's your in your profile. So go get that checklist. So if you want the checklist, you're gonna go to businessbaddie.com/checklist, to get access to that checklist immediately. It goes through the eight things that you need on your Upwork profile, and you'll get access to it immediately.


Brandi: I want everyone to go grab that checklist. We will put the link in the show notes so you have that. It'll also be on the blog, so you can go li read the episode, grab those tips, and we'll link it in there.


So you have many places that you can go grab that checklist completely free from Ashley, and she has a ton of other resources for you on upward, whenever you're ready for the next step. So Ashley, thank you so much. For coming on and sharing this with our guests, but I like to do some rapid [00:19:00] fire. So are you ready for this?


Ashley: Ready? 


Brandi: Okay. So what is your favorite business book? 


Ashley: Oh gosh, right now it is building a Second Brain. 'cause I'm just horribly unorganized. So I'm learning to be more organized and that's actually, it's opened up a lot. For me to be more organized in how to actually do it. So I love that book. 


Brandi: Did I recommend that?


Ashley: Yes, 


Brandi: that is, yeah, we, I was about to say, that's a book that I recommend. I like that book. Okay, perfect. So favorite big to this book, building A Inside Brain, and then two, how do you like your taco? 


Ashley: Oh man, I like a hard taco. I like a beef hard taco with cheese. Or I like al Pastor, like the traditional Mexican style is like my all time favorite with a little pineapple.


Brandi: Huh? Everyone who says pineapple, I'm like, I do not want a sweet taco. Like 


Ashley: it's not sweet. 


Brandi: Sweet 


Ashley: though. 


Brandi: It's not wanna like savory one. No. And I love how you didn't flinch at that question. Most people are so taken aback by that [00:20:00] question and you were just like, oh, this iss how I ordered my taco. Normal question.


Like whatever. And then tell me what's the best piece of business advice you've ever received? 


Ashley: Ooh, that's a good question. Honestly just jump just do it. Get into action. That's, that's truly, I think for me, I'm a trial by fire girl, so having that permission to just do it messy was always the thing that I needed to be successful.


So I, that's the piece of advice that I really appreciate. 


Brandi: And then final question. What are you either loving or learning in your business right now? 


Ashley: Ooh, I am loving and learning my webinar process. Actually, I do run a webinar for land premium clients on Upwork, and I am loving, refining it.


Like I traditionally in the past have jumped ideas and jumped webinar classes all the time. But I've committed to Brandy to stick the path of this one webinar for a while, and I love it. Like I'm finding all of these [00:21:00] little ways to make it better and better and to give more value. And it's just been such a fun process.


So I think that's my, the thing that I love most right now. 


Brandi: I've been running the same workshop for the last six years for conversions for clients. Like people don't understand that that is the path to success as you continue to do the same thing over and over and over and over and over, as long as it's producing results.


And so you staying true to that webinar and optimizing it and refining it serves you so much better than jumping around to 10 different ways to sell your product. Ashley, thank you so much for being on the podcast. We've loved hearing about Upwork. Everyone go drive her checklist and also give her a follow on Instagram.


What is your Instagram, Ashley? 


Ashley: It is@the.business dot badie. It's very long, but it's, it's great. 


Brandi: We will link that up in the show notes as well. Thank you so much, Ashley, for telling us all about Upwork.