CrossOver, a Remote Jobs site, Axed By AI?
Joe Liemandt became a multi-billionaire by turning computer programming into factory work. But is AI making that business model obsolete?
This is a supplementary companion article to “AI Schools, the Future of Education?”.
CrossOver claims their services are used by “over 70 companies”. Yet, as of June 2025, their client list contains a mere handful of companies owned by Trilogy, founded by multi-billionaire Joseph Liemandt… who also owns CrossOver itself!
The site is full of remote work centered marketing but hardly any remote jobs. What’s up with that?
CrossOver
Imagine how many people around the world would leap at the chance to apply for a relatively high paying remote job. So why are they employing multi-level marketing tactics?
Take a look at the video titles from the CrossOver channel on YouTube:
“Have You Got What it Takes to Land a World Class Remote Job?”
“An Accountant In Pakistan Can Grow His Career While Having More Time For Family”
“Crossover Rockstar | How a Software Engineer In Mumbai Can Let The Code Just Flow”
“How a Crossover Rockstar Software Engineer in Sri Lanka Has Saved 2 Hours A Day”
“How Nadia from Romania became a Crossover Rockstar”
“Crossover Rockstars | How An Accountant in the Philippines Could Buy Her Own Condo”
“Crossover Rockstars | How a Senior Software Engineer from Egypt Can Work Remote to Stay Near Family”
Well, clearly it’s working. Collectively these few videos have millions of views. On LinkedIn, CrossOver has 8 million followers.
When asked about his experience working at Trilogy, Sameer Dholakia, CEO of SendGrid, said:
“The joke was it was cult-like because it was cult-like. […] But I loved that.”
Getting the Gig
"Here’s Why Crossover is a Scam" provides ground level insight on how CrossOver operated in 2016-2018.
Crossover will promise you a virtual utopia […] allow me, please, to call BS.
Now, before you label me as a disgruntled employee […] note that since my contract was terminated a year ago, I started a new business (my third), and am happily living my 30s doing less and earning more than I ever had.
In fact the only reason I’m writing this is that I’ve got enough time on my hands to worry about other people.
I like that!
Marcus describes the job application process as taking months, not “a week”. Throughout the lengthy process; applicants aren’t given timely assurance if they’re doing well or getting rejected.
Applicants need to be willing to work 40 to 50 hours per week, but are ultimately hourly contract workers.
You’ll only get paid for however much you manage to work in a week, so if there’s just 2 hours’ work this week you’ll only get 2 hours worth of pay.
Trilogy gig workers need to install WorkSmart, spyware that monitors mouse clicks, takes screenshots, and streams photos and video from their webcam. “If you’re not doing anything wrong, you have nothing to fear”, claims CrossOver.
…if your resume was internally marked as a ‘1’, even if by mistake, you can part waters and shit gold during the assessment, you won’t be hearing back before next Hanukkah.
Allegedly, regardless of whether an applicant can get the gig, they’re told to do the sample “real-world work assessment”.
An employer asking for unpaid work is already a huge red flag, but asking that all applicants do a significant amount of unpaid work…
It begs the question, are they exploiting free work from applicants desperate to impress hiring managers?!
Crossover’s marketing strategy for 2018 is to show prospective clients that their [hiring] tournaments are massively successful.
Acquiring a large pool of top applicants would make CrossOver’s services appealing to third-party clients looking to hire… in theory. But it’s likely that CrossOver solely exists as the vertically integrated recruiting wing of Trilogy.
A Global Software Sweatshop
A Forbes article from 2018, “How A Mysterious Tech Billionaire Created Two Fortunes—And A Global Software Sweatshop” by Nathan Vardi, provides a more comprehensive overview of CrossOver.
Joe Liemandt became a multi-billionaire by running ESW Capital, a private equity firm that buys US software companies, strips them of their US employees, and re-staffs with foreign developers they can pay “cloud wages” to.
Tryba argues that the current cloud wage for a C++ programmer, for example, is $15 an hour. That’s what Amazon pays its warehouse workers.
Crossover, which is actually the recruiting wing of ESW, has amassed an army of 5,000 workers in 131 countries from Ukraine to Pakistan to Egypt. In the past 12 years, ESW has quietly acquired some 75 software companies, mostly in the U.S., and it exports as many as 150 high-tech jobs every week.
Granted, these are low wages by US standards, but can be life changing relative to how far the dollar goes in other countries.
Spyware or not, programmers are applying in droves, and it’s made Liemandt richer than ever. At age 50 he’s back on The Forbes 400, with a net worth of $3 billion. But rather than celebrate his return, he refused to speak to Forbes for this article. “I am very private; I am an introvert,” Liemandt said to Forbes in 2017.
His preference for anonymity is no surprise. Liemandt’s metamorphosis has transformed him from every dorm-room coder’s hero to an ominous force in tech as his expanding global cloud-force pushes down wages and turns computer programming into factory work.
Liemandt was also a patent troll. ESW Capital purchased Versata in 2006, since then it’s been wielded in lawsuits against 20 companies: ranging from SAP (won $345 million), Sears (settled for $175 million), and Ford (won $104 million). Several of these were overturned later though.
Versata Development Group, Inc. v. SAP America, Inc. became a landmark case, since it was overturned in 2015 due to Versata’s patent being deemed ineligible, due to its basis on abstract ideas.
Regarding Versata Software Inc. v. Ford Motor Co., in 2023 a judge reduced the jury’s $82.3 million contract damages award to just $3 in nominal damages and eliminated the $22.4 million verdict for misappropriation of trade secrets.
Turning Programmers into Human CPUs
In a 2021 followup article, “The Billionaire Who Pioneered Remote Work Has A New Plan To Turn His Workers Into Algorithms”, Vardi describes the inner workings of CrossOver in vile detail via leaked internal documents.
Remote staffing is now ubiquitous, so Liemandt has decided to take his operation to the next level. His workers have been told by their managers that the goal is to turn them into “algorithms” and “human CPUs.” At the same time, Liemandt has updated his acquisition process with a new playbook, obtained by Forbes, with an eye toward purchasing one company each week.
To train workers to fix software bugs or handle customer help requests, new Crossover workers complete four weeks of “remote university” after they are hired, people familiar with the process say. The training, sometimes referred to as a camp, “teaches leading-edge programming practices based on the software factory theory.” The workers are taught to perform work units that are constantly assessed. If the workers do not perform adequately at remote university, their contracts are terminated, even if they just left a job to become Crossover workers.
During remote university, new employees must pass an additional proctored cognitive test. Workers must get 35 of 50 math and word problems right; some jobs require 40 correct answers. Most people who start remote university are either dismissed or quit after the four weeks. Once they start working, the tasks Crossover workers perform are constantly assessed. They can be demoted and are dismissed at any time, people familiar with Crossover say. The attrition rate is about 69% annually.
Unlike Google, Microsoft, Nvidia and Amazon, who compete fiercely for promising programmers from top universities, Liemandt’s hourly workforce was largely expendable, with his operation casting off and replacing workers on a routine basis.
In a video titled “My Experience with CrossOver”, Waleed El Nimer explains that to play it safe during his three month application process, and even a month after getting hired as a financial analyst, he spent 8 hours a day working his current job and 8 hours a day on the CrossOver application process. Brutal!
Unlike CrossOver’s marketing claims, the reality is that US corporations don’t want to pay “Silicon Valley salaries” to anyone, anywhere. Trilogy was thinning wages to fatten profits, not altruistically spreading tech industry wealth around the world.
That was just a small byproduct of a system designed to make a billionaire even more grotesquely wealthy.
What Now?
In 2025, are CrossOver and UpWork still in a neo-colonial race to outsource US jobs?
Well, the lack of jobs listed on CrossOver seems to indicate that like the rest of the tech industry, Trilogy might be downsizing. CrossOver’s business model could become obsolete soon if AI can replace junior developers.
Also, surely Liemandt would say his real passion in life isn’t soul sucking private equity or patent trolling: it’s teaching entrepreneurship.
Hence, Liemandt’s focus has shifted to the development of 2 Hour Learning (2HL) software for several “AI-powered” schools.
Teachers Wanted?
In a post on the “Teachers in Transition” subreddit, a teacher shared their experience applying for a $200k job at Novatio School (not remote), which uses 2HL.
I progressed far in the process, submitted detailed assignments, and in the most recent application, was invited to an interview.
After being told that I was not successful, I then received a Calendly invite for an interview. Confused but hopeful, I scheduled and prepared thoroughly. On the day of the interview, I waited in the Google Meet room—only for no one to show up. I was left in the dark, with no communication or follow-up.
I have received zero feedback, and after repeated attempts to gain clarity from both Crossover and Novatio, I still have no idea what happened or why the process was handled so inconsistently.
[…] complete lack of respect for applicants’ effort, time, and emotional investment.
Could these job listings be fake?
On r/teacher another user had the same thought, “Is this real?”, reacting to a crazy job offer to work at GT School, another AI school that uses 2HL.
Unfortunately it’s become common for companies in the US to post fake job ads. 40% of companies posted a fake job listing in 2024, according to a survey of 650 hiring managers. Inflated job boards can help companies look like they’re growing to investors, even when they aren’t.
Yet another 2HL front, Alpha School, is opening seven new schools in Fall 2025. Certainly they have a real need to hire staff… and all that labor could cost a pretty penny!
Conspiracy for Hire
AI hasn’t replaced teachers or software engineers, but what if it’s replacing recruiters?
It’s possible that Trilogy is using another one of its holdings, IgniteTech, to automate hiring workflows. That could explain why applicants simply get ghosted at the interview stage.
Is CrossOver harvesting free labor under the guise of “job applications”?
I’ve got no proof of that… but it seems Gauntlet AI is doing it openly!
Gauntlet AI
“Thirty yards of board fence nine feet high” - Tom Sawyer
The most Elite AI-First Engineers in the world don't apply to jobs -
they finish the Gauntlet.Complete the Gauntlet. Receive a $200k/yr offer as an AI Engineer.
Gauntlet AI is a thousand hour long job application. No joke.
Applicants are “challenged” to spend 80 to 100 hours per week, for 5 weeks in training/preparation and 5 weeks (up to 500 hours) working on real projects provided by hiring partners, which are… you guessed it… all owned by Trilogy (Liemandt)!
Zero tuition. All expenses paid.
Yup that’s right, you get to do $7,500+ worth of work for a billionaire: free of charge! (Based on Austin’s $15/hr minimum wage.)
Incredibly though, they’ve already convinced a cohort of “students” they’re just one yard of whitewashed fence away from earning the big bucks.
It’s a clever scheme: rebranding an unpaid internship as hands-on learning.
Call it the “real-world work assessment” of a “job application”.
“Does a boy get a chance to whitewash a fence every day?”
That put the thing in a new light. […]
“Say, Tom, let me whitewash a little.”