Upwork Customer Service: A Case Study of What Not to Do
Bad Web Design, Bad Operational Policies, and Bad Employee Training Can Easily Turn Into Bad Press
Last Sunday, August 10, 2025, I saw on my calendar a little reminder to cancel my monthly paid subscription to Upwork.
If you’re unfamiliar with Upwork, Hayden Brown, its President & CEO, on their website, touts it as “the world’s work marketplace where every day businesses of all sizes and independent talent from around the globe meet . . . to accomplish incredible things.” Business for Upwork appears to be quite good—they reported $4.0 billion in gross services volume (GSV), $215.6 million in net income, and $167.6 million in adjusted EBITDA for 2024 in their Form 10-K Annual Shareholder Report filed with the SEC on February 13, 2025. Here’s a nice results of operations summary for the past three years:
Things look to be decently good for Upwork. They have no good reason (certainly not any financial one) for not doing all they can for “best in class” service provision like I like to tout and excel at. Great!
(As a little aside, look at this graph also from their 10-K . . . that COVID-19 spike in their cumulative total return was massive, as I guess we ought to have expected. Wow!)
But I digress too much . . . back to the case study in bad web design, bad operational policies, and bad employee training.
I had placed that cancelation calendar reminder back in mid-July when I saw the latest-at-the-time $19.99 monthly fee hit my bank account. I had joined Upwork back on May 13, 2025 at the suggestion of a few people as a way to potentially have a little bit of cash flow and activity while I geared back up from my 6.5 years dealing with the aftermath of the bicycle accident back in 2016. I gave Upwork my attention quite a bit for those two months, but by mid-July, I was getting too busy with The Second Bill of Rights book and overall project, my strategic advisory businesses, Substack writings, and all the other initiatives and projects that I love so much. I just didn’t have the time to check it every day or even once a week PLUS, in those two months of activity on Upwork, I hadn’t really found many opportunities appropriate or even plausible for what my background, experience, and expertise are. I think I had one opportunity turn into a Zoom call only to have the company I spoke with ghost on me. Oh well . . .
So, my Sunday, August 10th account cancelation calendar reminder came up and I went to the Upwork website and canceled my account with days to spare . . . or at least that’s what I thought I had done.
I happened to log into my bank account on Wednesday morning, August 13, 2025 and immediately saw that Upwork had charged me another $19.99 for yet another month of usage that I was never going to utilize much like I hadn’t utilized it the month prior. I promptly logged back onto their website searched around for the actual account cancelation functionality and canceled it for real. The account cancelation functionality is not that easy to locate as compared to merely the account deactivation functionality. I’d fix that if I were you Upwork and Ms. Brown.
Bad web design . . . I see you!
Right after that, at 9:26am ET, I sent Upwork an email on their Contacts webpage endeavoring to get my $19.99 refunded to me. Easy, normal stuff.
Roughly 18 hours later at 3:48am ET (?!?!?), “Johnabi” at Upwork responded saying in pertinent part:
“I’ve carefully reviewed your account and also consulted with our team. Based on our findings, it appears that your membership was downgraded after the monthly charge had already been processed.
Because Upwork’s system immediately applies membership perks to your account upon renewal or upgrade, we’re unable to issue refunds for membership charges. These benefits are non-reversible once assigned.”
The timing and substantive content of Upwork’s response felt and still feels very robotic and non-human, yet trying to seem human. (Maybe it was handled overseas?) I’d fix that too if I were you Upwork and Ms. Brown.
Bad operational policies . . . I see you!
When I read Upwork’s response, I was a bit surprised at how short-sighted and non-human feeling it was. There’s nothing wrong with automation, but it’s August 2025 . . . an AI-driven, dynamic response system for procedural communications and escalation to a real human is less than $100/month from a variety of SaaS vendors. Splurge, Upwork! Splurge!
At 8:32am ET, I replied back saying in pertinent part:
“I think this ought to be a nice seed for another one of my ‘best practices’ articles across my social media platforms.”
At 7:26pm ET, “Joanne” at Upwork responded saying in pertinent part:
“I'm pleased to let you know that I've coordinated your concern to our team and received approval to issue the refund or your last renewal as a one-time courtesy.”
At 9:32pm ET, I responded saying in full:
“That's nice to hear, Joanne, but now things are a bit different. I already have the article scheduled for this coming Monday morning and an outline prepared. Share this with whomever needs to see it on up the chain of command there.”
Roughly 13 hours later, at 11:02am ET on Friday, August 15, 2025, “Joanne” at Upwork responded again, but there’s nothing pertinent or even slightly relevant in that message to even quote.
And, that was the end of my communication with Upwork. I think they’ve now sent 3-4 automatic “rate our performance” emails all of which I’ve just ignored.
It goes without saying, but I’m still going to say it loudly, that all those messages also felt and still feel VERY robotic and non-human, yet trying to seem human. I’d fix every little bit of that training and protocol too if I were you Upwork and Ms. Brown.
Bad employee training (I guess???) . . . I see you!
My $19.99 refund hit my bank account on Friday for whatever that means . . . it’s only $19.99, remember.
This was on an account that had barely, if at all, been used in a month. It’s just bad business practices through and through.
So, this is just another little drip or drop of:
Bad press for Upwork.
Don’t be like Upwork in your business or work.
Review your website, operational policies, and employee training at least every quarter given how rapidly technology is changing to make situations like this NEVER even come close to happening for insignificant expense, if even any at all.
Hire an outside “secret shopper” even to try to break or stress-test your systems.
You can find someone to do so cheap on Fiverr, Freelancer, or even Toptal (if you need someone higher skilled).