I took the call from a car parked next to a gravel pit somewhere in rural Romania, because my friend was late and I had a ten-thousand-dollar-a-month conversation scheduled.
It worked anyway. That call won me my first Upwork client as an IT consultant and kicked off my actual consulting career. The client, Karl, needed a SharePoint Online specialist for a US biotech startup. Don't you believe me? Well, check my LinkedIn profile. It's under HiFiBio.
It was not luck. It was the payoff of years of projects done for peanuts. If you think I was charging 100 dollars an hour from day one - please.
Here is what actually made the difference, and what I would tell anyone with real experience trying to do the same today.
First Upwork client as an IT consultant
But first we have to be honest about Upwork itself. Upwork is not the platform it was ten years ago. I wrote an article about it, and I think It's getting worse... But if you want to start, I have another article about it
It went public, which means its primary focus is returning cash to shareholders. Everything they do now optimizes their own revenue, which isn't always aligned with your interests as a freelancer. If you don't understand that, you will be constantly frustrated.
Two more honest points before you invest time there:
- If you do not have solid experience backed by facts, certifications, and demonstrable achievements, there is very little there for you right now.
- If you plan to compete on price, you are in a losing position before you start. You will not beat freelancers from countries with a fraction of your living costs, and you should not try.
Upwork is a global market where companies in Germany, the UK, and the US look for specific specialists and pay for that specificity. A Microsoft 365 security consultant is not a commodity there. That is exactly why the rate holds.
Your profile has three seconds. Stop writing it like a CV
The most common mistake I see from experienced IT people:
"I possess 10 years of experience in systems administration. I have completed training in network security. I am ready to undertake cooperation."
Nobody reads that. Clients arrive with a concrete problem and one question: does this person solve my problem?
The title is your billboard.
Not this: IT Specialist | Microsoft 365 | Azure | Cybersecurity
This: Microsoft 365 Security Expert - I protect SMB companies from ransomware and data breaches
The first is a list of skills. The second says what you do and for whom.
The overview: the first 150 characters are all they see.
Mine opened like this:
"I am an Upwork Top Rated Plus expert in Microsoft 365, cybersecurity, and related technologies. If your company runs Microsoft 365 and you are not sure your data is safe - that is exactly what I fix. No jargon. No overkill. Just the right protection for your company's size."
Problem, experience, promise. Three sentences.
Narrow beats broad. Thousands of "IT specialists" are on Upwork. There are a few dozen "Microsoft 365 security consultants for SMB". Less competition, higher rate, and clients who are actually looking for you.
No Upwork history yet? Three ways to fill the gap:
- Real projects with anonymized client data - "deployed Conditional Access for an 80-person company, zero incidents in two years"
- A case study built in your own test tenant - an M365 audit, a Defender configuration, a report
- Certifications - MS-500, SC-300, AZ-500. They work here, because a client can verify them against your transcript
Certifications are a heavily emphasized part of my own profile and my proposals, for exactly that reason.
Below is an example from my Upwork profile. Here's the link as well.
Landing your first Upwork client as an IT consultant is a filtering problem
Not a volume problem. Do not apply to everything.
Look for postings where the client has a verified payment method, has hiring history on the platform, posts a budget realistic for your rate, and writes a specific description rather than a vague one.
Your first client matters because they give you your first review, and reviews are the currency of the platform. One strong review from a serious client opens more doors than five cheap jobs.
One warning, from a mistake I made myself. If a client asks you to produce work to "prove you know your stuff" - walk away. They will keep asking for more, they will not pay because tests are not paid, and you will not get the job. The trick is that they run this with ten hopeful freelancers, hire nobody, and get the work done for free.
If a client wants something built, they pay for it. Full stop.
Also: watch your Job Success Score. It is the single most important indicator on the platform, and protecting it should shape which jobs you accept.
A proposal structure that gets replies
Most cover letters open with "I am an experienced professional with 10 years of..." and end there.
Yours has to prove you read the posting. Four parts:
- One sentence showing you understand their specific problem
- One sentence of your experience with exactly that problem
- What you propose as a first step
- A question, to start a conversation
Example:
"I see you are looking for someone to secure your M365 tenant after a recent phishing incident - a common problem after a cloud migration. I secured a similar environment for a 60-person financial services firm after exactly this scenario. I would suggest starting with a configuration audit, which gives you a full risk picture within 48 hours. Can I ask which third-party applications you have integrated with M365?"
Three sentences and a question. Not an essay, not a certification dump.
The mistake that costs people months: pricing from fear
New specialists reason like this: no reviews yet, so I have to be cheaper.
On Upwork a low rate does not attract clients, it repels them. A client shopping for an IT security consultant who sees 25 dollars an hour thinks: what is wrong with this person?
And in my experience, clients who buy on price are the ones who cause the most trouble - the most demanding requirements, the most availability expected, the least willingness to pay for any of it.
Set your rate on the value you deliver, not on fear of rejection.
What actually won me first Upwork client as an IT consultant
The client needed help with SharePoint. He was an academic who also happened to run IT at the startup.
He saw two things. He saw that I wanted the work - I took that call from a gravel pit rather than reschedule. And he saw that I genuinely knew SharePoint: the limits, the traps, what could and could not be done. Every problem he raised on that call, I had an answer for in real time.
There is a second half to that story, and it is the part that mattered more. I did more than they expected. After about a year we moved off the platform to a direct B2B contract.
Two things changed at once. I started earning money I could only have dreamed of in my local market. And I started building things almost nobody around me had touched yet - the whole modern workplace stack, Intune, device management at scale. Working as an in-house consultant let me gain experience that turned out to be priceless.
That project gave me both the confidence and the skills that everything since has been built on.
Bottom line
On Upwork the cheapest person does not win. The most specific person does - specific profile, specific specialisation, specific proposal, specific rate.
Your 15 or 20 years in IT are not something to hide behind a discount. They are your strongest card.
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