To revist this article, visit My Profile, then View saved stories.To revist this article, visit My Profile, then View saved stories.Caitlin HarringtonFive months ago, Software engineer Shikhar Sachdev adopted a peculiar hobby. While his friends met for drinks or played FIFA 23 to unwind after work, he would come home, boot up his laptop, and spend hours filling out job applications, for sport.Sachdev is content with his job at a San Francisco fintech company, but he writes a career blog in his spare time and had noticed a recurring sentiment: Job hunting these days is the worst. Friends described returning home from an exhausting day of work they hated, applying for new positions, and quickly growing discouraged by clunky Application software and a low response rate. Research suggests the frustration is widespread: 92 percent of candidates abandon online job applications before completing them, according to the recruitment platform Appcast.“You might hate your boss. But if you think that searching for jobs is worse, you're never going to change,” Sachdev says. “I wanted to try to put some data behind the claim that job hunting sucks.”Sachdev set himself the challenge of applying to 500 software engineering jobs to observe exactly what made the endeavor more or less frustrating. Halfway through, however, he hit a snag. “I wanted to chop my head off,” Sachdev says. He scaled back his target to a still brain-melting 250 jobs across a range of industries and company sizes, chosen largely at random—companies he’d seen on billboards, for instance, or friends’ employers.Sachdev timed each application from start to finish and for consistency always applied directly through a company’s career page—he ended up spending about 11 hours total filling applications. Since he wasn’t looking for a new position, he always stopped short of clicking “Submit” on a completed application, except for a few choice roles that piqued his interest. (He landed three interviews, but didn’t pursue the jobs.) He aimed to make each application serviceable, but wasn't as thorough as a truly ambitious or desperate job seeker would be, so he figures the times he logged are underestimates.Sachdev found it took an average of 2 minutes and 42 seconds to fill out a job application—but that doesn’t include time spent identifying suitable roles, and the time could vary widely from job to job. The longest took more than 10 minutes, the shortest less than 20 seconds. Much of this variation sprang from the particularities of applicant tracking software.Matt BurgessNiamh RoweJulian ChokkattuSimon HillApplying to work at a company that used Workday, for instance, took 128 percent longer than average for similarly sized companies in the same industry. Workday spokesperson Nina Oestlien called customer service a “core value” at the company and says that application timing is determined by how customers configure their applications. (Disclosure: WIRED owner Condé Nast uses Workday. Also, we’re hiring!)Sachdev’s job hunting obsession was born partly from rejection. Originally from Geneva, Switzerland, he graduated from UC Berkeley in 2019 with a degree in environmental economics and philosophy. Most of his friends lived in the Bay Area, and career opportunities in the region abounded, so he resolved to stay.As Sachdev’s senior year wound down, he began furiously applying for local jobs. But his heart sank each time he reached the portion of an application that asked if he needed visa sponsorship. Since he lacked US citizenship, he needed an employer to sponsor him, likely with a specialty H-1B worker visa. “When I would click the H-1B box, my application would go straight into the garbage,” he says. “I was getting rejections four minutes after I applied.”But Sachdev has the tenacity to power through the uttermost tedium for months on end. And he discovered what looked like a loophole. Foreigners who earn STEM degrees from certain US institutions can work in the country for up to three years without a visa under a federal program called Optional Practical Training. “Who stays at their first job for more than three years?” he rationalized. So when the visa sponsorship question popped up in an application for a product manager role at a major tech company he wanted to work for, he clicked “no.”Matt BurgessNiamh RoweJulian ChokkattuSimon HillAfter he landed an interview, Sachdev spent 40 hours scouring job sites for tips, cramming his notebook full of hypothetical questions and their responses, compiling a presentation the company required—and totally neglecting his coursework. Half a dozen interviews later, he got the job. His heart soared, but not for long. When he explained his immigration status to the recruiter, she rescinded the offer. Sachdev started over, eventually landing a job with a startup willing to sponsor his H-1B visa, and decided to parlay his experience into a career blog offering help to other hapless job questers.Job hunters have long complained about the process, but it developed fresh annoyances after moving online starting in the mid-’90s, says Chris Russell, managing director of the recruitment consultancy RecTech Media. Online job boards like Monster and CareerBuilder flooded companies with candidates, giving rise to applicant tracking systems built to help recruiters manage the deluge.These systems promised to save recruiters time by automatically ranking and filtering applicants based on keywords. From the perspective of applicants required to laboriously enter their information into the software, they felt like a new barrier. “These systems were built with the companies in mind,” says Russell. “They never really considered the user experience from the job seeker’s point of view.” A cottage industry sprang up of tools and résumé whisperers promising to help job seekers get past the automated scanners.In recent years, new features like psychological assessments and “digital interviews,” in which applicants answer prepared questions into their webcams, only placed more barriers between candidates and human decisionmakers. Meanwhile, the fundamentals of hiring remain stuck in the past, says Scott Dobroski, a career trends expert at jobs platform Indeed. It takes three and a half months for most Indeed users to find a job, he says. “All the other parts of our lives have sped up. The hiring process has not caught up.”While job hunters have much to gripe about, from “ghost jobs” to the dreaded “résumé black hole,” Sachdev decided to focus his efforts on the initial application process. He identified three main factors that affected the time it took to apply: the size of a company, the industry it was part of, and the applicant tracking software it used.Applicant tracking software was a major source of Sachdev’s frustration. The most common systems he encountered were Workday, Taleo, Greenhouse, Lever, and Phenom, which adds AI-powered features on top of systems like Workday. More established systems such as Workday and Taleo redirected him away from the careers page and made him create a separate account for each application, adding significant time and vexation. By the end of his 250 applications, he had 83 separate accounts.Matt BurgessNiamh RoweJulian ChokkattuSimon HillNewer offerings such as Greenhouse and Lever spared him some of these frustrations. Applications through Lever, for instance, took 42 percent less time to complete than the average for similarly sized companies in the same industry.Sachdev also spent many excruciating minutes retyping information he’d already uploaded on his résumé because software would misread it. Workday, for instance, would routinely populate the education field with “Munich Business School” even though Sachdev’s résumé clearly says he graduated from non-soundalike UC Berkeley. “Sometimes it's not even the time,” he says. “It's the mental fatigue of having to do it every single time.”The longest application to fill out was for the US Postal Service, clocking in at 10 minutes and 12 seconds, while the shortest was that of hedge fund Renaissance Technologies, which requested only his name and résumé and consumed a mere 17 seconds. In general, Sachdev found that government applications took the longest—a trend that Indeed’s data backs up—followed by aerospace and consulting jobs. Younger industries such as online banks, AI firms, and crypto companies were amongst the least time-consuming. Legacy banks, for instance, took about four times longer to apply to than their newer online counterparts.Sachdev also found applications to large companies more time-consuming than for smaller firms. In general, a doubling of company size added 5 percent to the average application time.While the process was largely an exercise in repetition, Sachdev encountered a few creative takes on a musty old format. Plaid, a fintech company that provides APIs to connect software with bank accounts, invited applicants to apply via API. (Sachdev opted for the old-fashioned route, for consistency.) The gaming company Roblox let candidates apply in-game.While hiring software has historically been stacked in employers’ favor, more job seekers are using their own forms of automation. Bots and tools like LazyApply use text-generation technology like that behind ChatGPT to automatically mass apply to jobs, to the likely chagrin of overwhelmed recruiters. When Sachdev posted his results on discussion site Hacker News, one commenter claimed to use bots to fill out job applications and ChatGPT to write cover letters and correspond with recruiters, fully taking over only at the interview stage. “Can you blame him?” Sachdev says. “Because the companies are doing it too. Their résumé parsers, their application tracking software, and their tools are also using AI. So it's almost as if the applicant now has this weapon they can use against the companies.”Matt BurgessNiamh RoweJulian ChokkattuSimon HillAn AI arms race that floods the job market with unserious applicants and insurmountable filtering tools is in nobody’s interest, however. Indeed’s Dobroski says some platforms, including his own, have begun rolling out a new approach that aims to save time on both sides, albeit also by leaning on algorithms. Instead of sending hundreds of résumés into the void and hoping for the best—“spray and pray” he calls it—candidates can list their skills, qualifications, and preferences and let AI suggest suitable jobs to apply for. “The matching really speeds up the hiring process, and it connects the candidate with employers that they otherwise may not even have considered,” he says.Sachdev has his own ideas for what would make job applications more productive for both seekers and recruiters. First off, he advises applicants to save time and mental anguish by prioritizing employers that use simpler software like Lever and Greenhouse. For jobs he’s really serious about, he’ll try to make a human connection with the hiring manager on LinkedIn.There’s a saying Sachdev likes, from computer science professor Randy Pausch: The brick walls are there for a reason. Facing and surmounting hurdles can help a person discover how much they want something. But if an employer erects too many barriers, “is an applicant really going to think, ‘That brick wall is there for a reason?’ Or is the applicant going to exit out of your website and go apply somewhere else?” Sachdev says. “I think it's the latter.”WIRED has teamed up with Jobbio to create WIRED Hired, a dedicated career marketplace for WIRED readers. Companies who want to advertise their jobs can visit WIRED Hired to post open roles, while anyone can search and apply for thousands of career opportunities. 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