The design of getting hired
On knowing your audience, clarity over cleverness, and why slow is smooth
A thousand people applied for a single back-end engineering role. Only forty made it to serious consideration. One person got the job. These aren’t unusual numbers in tech hiring, but they highlight why thoughtful applications matter so much. To understand what makes the difference between landing in that stack of forty versus being lost in the pile, I sat down with Rotimi Lademo, Senior Technical Recruiter at Medium.
This summer, noticing candidates struggling in an increasingly tough market, Rotimi opened his calendar for resume reviews. What started as a few conversations expanded to over fifty meetings, each revealing common patterns in how people approach—and often mishandle—their job search.
“One woman emailed recently saying our conversation completely changed her trajectory and helped her land a new role,” Rotimi tells me. What made the difference? Rather than just offering generic advice, he shows candidates exactly how recruiters evaluate applications in real time, revealing the gap between presentation and reception—a process that often surprises even experienced job seekers.
The reality check
“I put up my screen and put the resume in one half and the job in the other,” Rotimi explains. “I show them how I would view this as a recruiter looking at both for the first time.” This side-by-side comparison often reveals an immediate disconnect between how candidates present themselves and what recruiters actually need to see.
While many candidates worry about AI gatekeepers, Rotimi explains the reality is more nuanced. “From the tools I have access to and that I’ve seen—the classics like Lever, Greenhouse, Pinpoint—they don’t use AI in the way candidates are thinking,” Rotimi explains. “Most of these companies don’t want to be adding a layer of their own judgment on who’s good and who’s bad. You still have to manually sort through the resumes, and recruiters really do have to read them.”
The fear factor
Fear makes us sloppy. When the pressure mounts to land a job, many candidates start firing off applications without strategy or care. “When you feel a certain amount of pressure, you start doing the opposite of what you should do,” Rotimi observes. “You start slinging resumes instead of taking a step back.” This fear-driven approach creates a vicious cycle: The more anxious we are about landing a role, the less thoughtful our applications become. The less thoughtful our applications, the fewer responses we receive. The fewer responses, the more anxiety.
This hits hardest for those with the most at stake. Early-career designers scramble to build portfolios. International candidates race against visa clocks. The urgency is real, but paradoxically, it often pushes people toward exactly the wrong approach.
Why slow is smooth
The conventional job search wisdom says cast a wide net—apply everywhere, pray something sticks.But in reviewing thousands of applications, Rotimi has found the opposite works: “Taking the time to thoughtfully customize a resume for one role will get you further than sending out dozens of generic applications.”
His advice? “Look for jobs every day, but don’t apply every day.” When you find a role that truly fits, that’s when you go all in—researching the company, tailoring your materials, reaching out thoughtfully to the team. Quality over quantity isn’t just a nice idea; in a flooded market, it’s your competitive advantage.
“If you find yourself applying to 5–10 jobs a day, that’s probably too many,” Rotimi posts on LinkedIn. “Slow down. The goal is to find one job.” In other words: Slow is smooth, smooth is fast.
The cover letter conundrum
Many candidates feel they need to supplement their applications with cover letters, but Rotimi takes a practical view: “A cover letter is not going to get you the job. But it might take you over the edge if you have everything else.” For someone applying to just five jobs a month and doing everything in their power to stand out, sure—write the cover letter. But don’t prioritize it over your resume.
The designer’s dilemma
For designers, there’s a particular irony at play. Designers who preach user-centered design often create resumes that prioritize aesthetics over usability. In trying to stand out visually, they create documents that actively frustrate their primary user—the recruiter trying to evaluate their fit.
“If I get a resume with size eight-point font from a designer,” Rotimi says, “that might tell me something about their design sensibility.” While your portfolio demonstrates craft, your resume reveals something equally important: Can you set aside your creative ego to serve user needs?
A recruiter who can’t easily parse your resume is unlikely to click through to your carefully curated portfolio. Every pixel-perfect project in your portfolio means nothing if your resume suggests you don’t understand basic user needs. The most common mistakes are surprisingly basic: microscopic fonts, bloated documents, missing portfolio links.
What actually works
Here’s what Rotimi looks for in resumes that most candidates miss:
Lead with impact: Skip the day-to-day tasks. A recruiter doesn’t care how many calls you made or emails you sent—they want to know what changed because you were there. Did you launch something? Fix something? Transform something? That's your opener.
Add context clues: “If you work at a company that’s not extremely well known, put a two- to three-word summary of what they do next to the company name,” Rotimi advises. That digital publishing startup might be perfectly relevant experience for Medium, but without context, a recruiter might skip right past it.
Mind the space: “Your work experience should start in the first 2/5 of the page,” he adds. If your experience starts near the center, you’ve taken up too much space talking about things that aren’t relevant. Remember: Recruiters scan before they read.
The pivot problem
Career transitions pose a particular challenge, especially in tech. While “early career” roles used to imply blank resumes, the landscape has changed. Like angling for a promotion—where you often have to prove that you’re already doing the job you want (protection against the Peter principle, perhaps)—candidates need relevant experience to make the leap.
“When it comes to early careers recruiting from a tech perspective, you need to have internships in the field, some experience that shows you can do the job here,” Rotimi says, relaying a conversation he had with other recruiters. “The amount of inertia you have to overcome, pivoting in a career is extreme. There’s just no one formula.” But there is a path: Create opportunities where none exist. Side projects. Freelance work. Find ways to build that bridge between where you are and where you want to be.
Beyond the resume
The thoughtfulness Rotimi advocates for—understanding your audience, crafting clear communication, showing genuine interest—extends beyond landing the job. “A ramp-up period isn’t about taking it slow,” he posts. “It’s really about how long it’ll take you to become fully productive—assuming you’re putting in maximum effort from day one.”
Whether you’re designing products or your career path, the best approach is to slow down and do things thoughtfully. Your resume isn’t just a requirement—it’s an interface between your experience and your future. Design it accordingly.
—Carly
Great resource to pass on to my mentees. Thanks for creating!
Great tips. I would like to understand how others have handled career pauses. Any good advice on presenting it?