Today’s my last day at Carta, where I got the chance to serve as their CTO for the past two years. I’ve learned so much working there, and I wanted to end my chapter there by collecting my thoughts on what I learned. (I am heading somewhere, and will share news in a week or two after firming up the communication plan with my new team there.) The most important things I learned at Carta were: Working in the details – if you took a critical lens towards my historical leadership style, I think the biggest issue you’d point at is my being too comfortable operating at a high level of abstraction. Utilizing the expertise of others to fill in your gaps is a valuable skill, but–like any single approach–it’s limiting when utilized too frequently. One of the strengths of Carta’s “house leadership style” is expecting leaders to go deep into the details to get informed and push pace. What I practiced there turned into the pieces on strategy testing and developing domain expertise. Refining my approach to engineering strategy – over the past 18 months, I’ve written a book on engineering strategy (posts are all in #eng-strategy-book), with initial chapters coming available for early release with O’Reilly next month. Fingers crossed, the book will be released in approximately October. Coming into Carta, I already had much of my core thesis about how to do engineering strategy, but Carta gave me a number of complex projects to practice on, and excellent people to practice with: thank you to Dan, Shawna and Vogl in particular! More on this project in the next few weeks. Extract the kernel – everywhere I’ve ever worked, teams have struggled understanding executives. In every case, the executives could be clearer, but it’s not particularly interesting to frame these problems as something the executives need to fix. Sure, that’s true they could communicate better, but that framing makes you powerless, when you have a great deal of power to understand confusing communication. After all, even good communicators communicate poorly sometimes. Meaningfully adopting LLMs – a year ago I wrote up notes on adopting LLMs in your products, based on what we’d learned so far. Since then, we’ve learned a lot more, and LLMs themselves have significantly improved. Carta has been using LLMs in real, business-impacting workflows for over a year. That’s continuing to expand into solving more complex internal workflows, and even more interestingly into creating net-new product capabilities that ought to roll out more widely in the next few months (currently released to small beta groups). This is the first major technology transition that I’ve experienced in a senior leadership role (since I was earlier in my career when mobile internet transitioned from novelty to commodity). The immense pressure to adopt faster, combined with the immense uncertainty if it’s a meaningful change or a brief blip was a lot of fun, and was the inspiration for this strategy document around LLM adoption. Multi-dimensional tradeoffs – a phrase that Henry Ward uses frequent is that “everyone’s right, just at a different altitude.” That idea resonates with me, and meshes well with the ideas of multi-dimensional tradeoffs and layers of context that I find improve decision making for folks in roles that require making numerous, complex decisions. Working at Carta, these ideas formalized from something I intuited into something I could explain clearly. Navigators – I think our most successful engineering strategy at Carta was rolling out the Navigator program, which ensured senior-most engineers had context and direct representation, rather than relying exclusively on indirect representation via engineering management. Carta’s engineering managers are excellent, but there’s always something lost as discussions extend across layers. The Navigator program probably isn’t a perfect fit for particularly small companies, but I think any company with more than 100-150 engineers would benefit from something along these lines. How to create software quality – I’ve evolved my thinking about software quality quite a bit over time, but Carta was particularly helpful in distinguishing why some pieces of software are so hard to build despite having little-to-no scale from a data or concurrency perspective. These systems, which I label as “high essential complexity”, deserve more credit for their complexity, even if they have little in the way of complexity from infrastructure scaling. Shaping eng org costs – a few years ago, I wrote about my mental model for managing infrastructure costs. At Carta, I got to refine my thinking about engineering salary costs, with most of those ideas getting incorporated in the Navigating Private Equity ownership strategy, and the eng org seniority mix model. The three biggest levers are (1) “N-1 backfills”, (2) requiring a business rationale for promotions into senior-most levels, and (3) shifting hiring into cost efficient hiring regions. None of these are the sort of inspiring topics that excite folks, but they are all essential to the long term stability of your organization. Explaining engineering costs to boards/execs – Similarly, I finally have a clear perspective on how to represent R&D investment to boards in the same language that they speak in, which I wrote up here, and know how to do it quickly without relying on any manually curated internal datasets. Lots of smaller stuff, like the no wrong doors policy for routing colleagues to appropriate channels, how to request headcount in a way that is convincing to executives, Act Two rationales for how people’s motivations evolve over the course of long careers (and my own personal career mission to advance the industry, why friction isn’t velocity even though many folks act like it is. I’ve also learned quite a bit about venture capital, fund administration, cap tables, non-social network products, operating a multi-business line company, and various operating models. Figuring out how to sanitize those learnings to share the interesting tidbits without leaking internal details is a bit too painful, so I’m omitting them for now. Maybe some will be shareable in four or five years after my context goes sufficiently stale. As a closing thought, I just want to say how much I’ve appreciated the folks I’ve gotten to work with at Carta. From the executive team (Ali, April, Charly, Davis, Henry, Jeff, Nicole, Vrushali) to my directs (Adi, Ciera, Dan, Dave, Jasmine, Javier, Jayesh, Karen, Madhuri, Sam, Shawna) to the navigators (there’s a bunch of y’all). The people truly are always the best part, and that was certainly true at Carta.

I’ve written about how I don’t love the idea of overriding basic computing controls. Instead, I generally favor opting to respect user choice and provide the controls their platform does. Of course, this means platforms need to surface better primitives rather than supplying basic ones with an ability to opt out. What am I even talking about? Let me give an example. The Webkit team just shipped a new API for <input type=color> which provides users the ability to pick colors with wide gamut P3 and alpha transparency. The entire API is just a little bit of declarative HTML: <label> Select a color: <input type="color" colorspace="display-p3" alpha> </label> From that simple markup (on iOS) you get this beautiful, robust color picker. That’s a great color picker, and if you’re choosing colors a lot on iOS respectively and encountering this particular UI a lot, that’s even better — like, “Oh hey, I know how to use this thing!” With a picker like that, how many folks really want additional APIs to override that interface and style it themselves? This is the kind of better platform defaults I’m talking about. A little bit of HTML markup, and boom, a great interface to a common computing task that’s tailored to my device and uniform in appearance and functionality across the websites and applications I use. What more could I want? You might want more, like shoving your brand down my throat, but I really don’t need to see BigFinanceCorp Green™️ as a themed element in my color or date picker. If I could give HTML an aspirational slogan, it would be something along the lines of Mastercard’s old one: There are a few use cases platform defaults can’t solve, for everything else there’s HTML. Email · Mastodon · Bluesky

Some major updates to our open-source Automerge library, an introduction to Sketchy Calendars, and a peek at our work on collaborative game development. Also some meta content—a refreshed website, and a talk about how we work.

Test UI outcomes, not API requests. Mock network calls in setup, but assert on what users actually see and experience, not implementation details.

Do you feel that the number of applications needed to land a role has skyrocketed? If so, your instincts are correct. According to a Workday Global Workforce Report in September 2024, job applications are growing at a rate four times faster than job openings. This growth is fuelled by a tight job market as well as the new availability of remote work and online job boards. It’s also one of the results of improved generative AI. Around half of all job seekers use AI tools to create their resumes or fill out applications. More than that, a 2024 survey found that 29 percent of applicants were using AI tools to complete skills tests, while 26 percent employed AI tools to mass apply to positions, regardless of fit or qualifications. This never-before-seen flood of applications poses new hardships for both job candidates and recruiters. Candidates must ensure that their applications stand out enough from the pile to receive a recruiter’s attention. Recruiters, meanwhile, are struggling to manage the sheer number of resumes they receive, and winnow through heaps of irrelevant or unqualified applicants to find the ones they need. These problems worsen if you’re an overseas candidate hoping to find a role in Japan. Japan is a popular country for migrants, thereby increasing the competition for each open position. In addition, recruiters here have set expectations and criteria, some of which can be triggered unknowingly by candidates unfamiliar with the Japanese market. With all this in mind, how can you ensure your resume stands out from the crowd—and is there anything else you can do to pass the screening stage? I interviewed nine recruiters, both external and in-house, to learn how applicants can increase their chances of success. Below are their detailed suggestions on improving your resume, avoiding Japan-specific red flags, and persisting even in the face of rejection. The competition The first questions I asked each recruiter were: How many resumes do you review in a month? How long does it take you to review a resume? Some interviewees work for agencies or independently, while others are employed by the companies they screen applicants for. Surprisingly, where they work doesn’t consistently affect how many resumes they receive. What does affect their numbers is whether they accept candidates from overseas. One anonymous contributor stated the case plainly: “The volume of applications depends on whether the job posting targets candidates in Japan or internationally.” In Japan: we receive around 20–100+ applications within the first three days. Outside of Japan: a single job posting can attract 200–1,000 applications within three days. ”[Because] we are generally only open to current residents of Japan, our total applicant count is around 100 or so in a month,” said Caleb McClain, who is both a Senior Software Engineer and a hiring manager at Lunaris. “In the past, when we accepted applications from abroad it was much higher, though I unfortunately don’t have stats for that period. It was unmanageable for a single person (me) reviewing the applications, though! “Given that I deal with 100 or so per month, I probably spend a bit more time than others screening applications, but it depends. I’ll give every candidate a quick read through within a minute or so and, if I didn’t find a reason to immediately reject them, I’ll spend a few more minutes reading about their experience more deeply. I’ll check out the companies they have listed for their experience if I’m not familiar with them and, if they have a Github or personal projects listed, I’ll also spend a few minutes checking those out.” For companies that accept overseas candidates, the workload is greater. Laine Takahashi, a Talent Acquisition employee at HENNGE, estimated that every month they receive around 200 completed applications for engineering mid-career roles and 270 applications for their Global Internship program. Since their application process starts with a coding test as well as a resume and cover letter, it can take up to two weeks to review, score, and respond to each application. Clement Chidiac, Senior Technical Recruiter at Mercari, explained that the number of resumes he reviews monthly varies widely. “As an example, one of the current roles I am working on received 250+ applications in three weeks. Typically a recruiter at Mercari can work from 5–20 positions at a time, so this gives you an idea.” He also said that his initial quick scan of each resume might take between 5–30 seconds. External recruiters process resumes at a similar rate. Edmund Ho, Principal Consultant for Talisman Corporation, works with around 15 clients a month. To find them, he looks at 20–30 resumes a day, or 600–700 a month, and can only spend 30 seconds to 2 minutes on each one before coming to a decision. Axel Algoet, founder and CEO of InnoHyve, only reviews 200 resumes a month—but “if you count LinkedIn profiles, it’s probably around 1,000.” Why LinkedIn? “I usually start by looking at LinkedIn—the companies they’ve worked at and the roles they’ve had,” Algoet explained. “From there, I can quickly tell whether I’m open to talking with them or not. Since I focus on a very specific segment of roles, I can rapidly identify if a candidate might be a fit for my clients.” Applicant Tracking Systems (ATS) Given the sheer volume of resumes to review and respond to, it’s not surprising that companies are using Applicant Tracking Systems. What’s more unexpected is how few recruiters personally use an ATS or AI when evaluating candidates. Both Ho and Algoet reported that though a high percentage of their clients use an ATS—as many as 90 percent, according to Ho—they themselves don’t use one. Ho in particular emphasized that he manually reads every resume he receives. Lunaris doesn’t use an ATS, “unless you count Notion,” joked McClain. “Open to recommendations!” Koji Hamane, Vice President of Human Resources at KOMOJU, said, “Up to 2023, we were managing the pipeline on a spreadsheet basis, and you cannot do it anymore with 3,000 applications [a year]. So it’s more effective and efficient in terms of tracking where each applicant sits in the recruiting process, but it also facilitates communication among [the members of] the interview panel.” The ATS KOMOJU uses is Workable. “Workable, I mean, you know, it works,” Hamane joked. “It’s much better than nothing. . . . Workable actually shows the valid points of the candidates, highlights characteristics, and evaluates the fit for the required positions, like from a 0 to 100 point basis. It helps, but actually you need to go through the details anyway, to properly assess the candidates.” Chidiac explained that Mercari also uses Workable, which has a feature that matches keywords from the job description to the resume, giving the resume a score. “I’ve never made a decision based on that,” said Chidiac. “It’s an indicator, but it’s not accurate enough yet to use it as a decision-making tool.” For example, it doesn’t screen out non-Japanese speakers when Japanese is a requirement for the role. I think these [ATS] tools are going to be better, and they’re going to work. I think it’s a good idea to help junior recruiters. But I think it has to be used as a ‘decision helper,’ not a decision-making tool. There’s also an element of ethics—do you want to be screened out by a robot? HENNGE uses a different ATS, Greenhouse, mostly to communicate with candidates and send them the results of their application. “ Everything they submit,” said Sonam Choden, HENNGE’s Software Engineer Recruiter, “is actually manually checked by somebody in our team. It’s not that everything is automated for the coding test—the bot only checks if they meet the minimum score. Then there is another [human] screener that will actually look over the test itself. If they pass the coding test, then we have another [human] screener looking through each and every document, both the resume and the cover letter.” How to format your resume The good news is that, according to our interviewees, passing the resume screening doesn’t involve trying to master ATS algorithms. However, since many recruiters are manually evaluating a high number of resume every day, they can spend at most only a few minutes on each one. That’s why it’s critical to make your resume stand out positively from the rest. You can see tips on formatting and good practices in our article on the subject, but below recruiters offer detailed explanations of exactly what they’re looking for—and, importantly, what red flags lead to rejection. Red flags The biggest red flags called out by recruiters are frequent job changes, not having skills required by the position, applications from abroad when no visa support is available, mismatches in salary expectations, and lack of required Japanese language ability. Frequent job changes Jumpiness. Job-hopping. Career-switching. Although they had different names for it, nearly everyone listed frequent job changes as the number one red flag on a candidate’s resume—at least, when applying to jobs in Japan. “There’s a term HR in Japan uses: ‘Oh, this guy is jumpy,’” Clement Chidiac told me. When he asked what they meant by that, they told him it referred to a candidate who had only been in their last job for two years or less. “And my first reaction was like, ‘Is that a bad thing?’ I think in the US, and in most tech companies, people change over every two to three years. I remember at my university in France, I was told you need to change your job externally or internally every three years to grow. But in Japan, there’s still the element of loyalty, right?” It’s changing a little bit, but when I have a candidate, a good candidate, that has had four jobs in the past ten years, I know I’m going to get questioned. . . . If I get a candidate that’s changed jobs three times in the past three years, they’re not likely to pass the screening, especially if they’re overseas. “Which is fair, right?” he added. “Because it’s a bit expensive, it’s a bit of a risk, and [it takes] a bit of time.” Why do Japanese companies feel so strongly on this issue? Some of it is simply history—lifetime employment at a single company was the Japanese ideal until quite recently. But as Chidiac pointed out, hiring overseas candidates represents additional investments in both money and time spent navigating the visa system, so it makes sense for Japanese companies to move more cautiously when doing so. Sayaka Sasaki, who was previously employed as a Sourcing Specialist by Tech Japan Inc., told me that recruiters attempt to use past job history to foresee the future. “A lack of consistency in career history can also lead to rejection,” she said. “Recruiters can often predict a candidate’s future career plans and job-switching tendencies based on their past job-change patterns.” Koji Hamane has another reason for considering job tenure. “When you try to leave some achievement or visible impact, [you have to] take some time in the same job, in the same company. So from that perspective, the tenure of each position on a resume really matters. Even though you say, ‘I have this capability and I have this strength,’ your tenure at each company is very short, and [you] don’t leave an impact on those workplaces.” In this sense, Hamane is not evaluating loyalty for its own sake, but considering tenure as a variable to assess the reproducibility of meaningful achievement. For him, achievement and impact—rather than tenure length itself—are the true signals of qualities such as leadership and resilience. Long-time or regular freelancers may face similar scrutiny. Though Chidiac is reluctant to call freelancing a red flag, he acknowledged that it can cause problems. “[With] an engineer that’s been doing freelance for the past three or four years, I know I’m going to get pushback from the hiring team, because they might have worked on three-, four-, five-month projects. They might not have the depth of knowledge that companies on a large scale might want to hire.” Also my question is, if that person has been working on their own for three or four years, how are they going to work in the team? How long are they going to stay with us? Are they going to be happy being part of a company and then maybe having to come to the office, that kind of thing? He gave an example: “If you get 100 applicants for backend engineer roles, it’s sad, but you’re going to go with the ones that fit the most traditional background. If I’m hiring and I’m getting five candidates from PayPay . . . I might prioritize these people as opposed to a freelancer that’s based out of Spain and wants to relocate to Japan, because there are a lot of question marks. That’s the reality of the candidate pool. “Now, if the freelancer in Spain has the exact experience that I want, and I don’t have other applicants, then yeah, of course I’ll talk to that person. I’ll take time to understand [their reasons].” How to “fix” job-hopping on your resume If you have changed jobs frequently, is rejection guaranteed? Not necessarily. These recruiters also offered a host of tips to compensate for job-hopping, freelancing stints, or gaps in your work history. The biggest tip: include an explanation on your resume. Edmund Ho advises offering a “reason for leaving” for short-term jobs, defining short-term as “less than three years.” For example, if the job was a limited contract role, then labelling it as such will prevent Japanese companies from drawing the conclusion that you left prematurely. Lay-offs and failed start-ups will also be looked upon more benevolently than simply quitting. In addition, Ho suggested that those with difficult resumes avail themselves of an agent or recruiter. Since the recruiter will contact the company directly, they have the chance to advocate and explain your job history better than the resume alone can. Sasaki also feels that explanations can help, but added a caveat: “Being honest about what you did during a gap period is not a bad thing. However, it is important to present it in a positive light. For example, if you traveled abroad or spent time at your family home during the gap period, you could write something like this: ‘Once I start a new job, it will be difficult to take a long vacation. So, I took advantage of this break to visit [destination], which I had always dreamed of seeing. Experiencing [specific highlight] was a lifelong goal, and it helped me refresh myself while boosting my motivation for work.’ “If the gap period lasted for more than a year, it is necessary to provide a convincing explanation for the hiring manager. For instance, you could write, ‘I used this time to enhance my skills by studying [specific subject] and preparing for [certification].’ If you have actually obtained a qualification, that would be a perfect way to present your time productively.” Hamane answered the question quite differently. “Do you gamble?” he asked me. He went on: “ When I say ‘gamble,’ ultimately recruiting is decision-making under uncertainty, right? It comes with risks. But the most important question is, what are the downside risks and upside risks?” “In the game of hiring,” Hamane explained, “employers are looking for indicators of future performance. Tenure, to me, is not inherently valuable, but serves as a variable to assess whether a candidate had the opportunity to leave a meaningful impact. It’s not about loyalty or raw length of time, but about whether qualities like resilience or leadership had the chance to emerge. Those qualities often require time. However, I don’t judge the number of years on its own—what matters is whether there is evidence of real contributions.” A shorter tenure with clear impact can be just as strong a signal as longer service. That’s why I view tenure not categorically, but contextually—as one indicator among others. If possible, then, a candidate should focus on highlighting their work contributions and unique strengths in their resume, which can counterbalance the perceived “downside risk” of job-hopping. Incompatibility with the job description Most other red flags can be categorized as “incompatible with the job description.” This includes: Not possessing the required skills Applying from abroad when the position doesn’t offer visa support Mismatch in salary expectations Not speaking Japanese Many of the resumes recruiters receive are wholly unsuited for the position. Hamane estimated that 70 percent of the resumes his department reviews are essentially “random applications.” Almost all the applications are basically not qualified. One of the major reasons why is the Internet. The Internet enables us to apply for any job from anywhere, right? So there are so many applications with no required skills. . . .  From my perspective, they are applying on a batch basis, like mass applications. Even if the candidate has the required job skills, if they’re overseas and the position doesn’t offer visa support, their resume almost certainly won’t pass. Caleb McClain, whose company is currently hiring only domestically, said, “The most common reason [for rejection] is the person is applying from abroad. . . . After that, if there’s just a clear skills mismatch, we won’t move forward with them.” Axel Algoet pointed out that nationality can be a problem even if the company is open to hiring from overseas. “I support many companies in the space, aerospace, and defense industries,” he said, “and they are not allowed to hire candidates from certain countries.” It’s important to comprehend any legal issues surrounding sensitive industries before applying, to save both your own and the company’s time. He also mentioned that, while companies do look for candidates with experience at top enterprises, a prestigious background can actually be a red flag—-mostly in terms of compensation. Japanese tech companies on average pay lower wages than American businesses, and a mismatch in expectations can become a major stumbling block in the application process overall. “Especially [for] candidates coming from companies like Indeed or some foreign firms,” Algoet said, “if I know I won’t be able to match or beat their current salary, I tell them upfront.” Not speaking Japanese is another common stumbling block. Companies have different expectations of candidates when it comes to Japanese language ability. Algoet said that, although in his own niche Japanese often isn’t required at all, a Japanese level below JLPT N2 can be a problem for other roles. Sasaki agreed that speaking Japanese to at least the JLPT N3 level would open more doors. Anticipating potential rejection points If you can anticipate why recruiters might reject you, you can structure your resume accordingly, highlighting your strengths while deemphasizing any weak points. For example, if you don’t live in Japan but do speak Japanese, it’s important to bring attention to that fact. “Something that’s annoying,” said Chidiac, “that I’m seeing a lot from a hiring manager point of view, is that they sort of anticipate or presume things. . . . ‘That person has only been in Japan for a year, they can’t speak Japanese.’ But there are some people that have been [going to] Japanese school back home.” That’s why he urges candidates to clearly state both their language ability and their connections to Japan in their resume whenever possible. Chidiac also mentioned seniority issues. “It’s important that you highlight any elements of seniority.” However, he added, “Seniority means different things depending on the environment.” That’s why context is critical in your resume. If you’ve worked for a company in another country or another industry, the recruiter may not intuitively know much about the scale or complexity of the projects you’ve worked on. Without offering some context—the size of the project, the size of the team, the technologies involved, etc.—it’s difficult for recruiters to judge. If you contextualize your projects properly, though, Chidiac believes that even someone with relatively few years of experience may still be viewed favorably for higher roles. If you’ve led a very strong project, you might have the seniority we want. Finally, Edmund Ho suggested an easy trick for those without a STEM degree: just put down the university you graduated from, and not your major. “It’s cheating!” he said with a chuckle. Green flags Creating a great resume isn’t just about avoiding pitfalls. Your resume may also be missing some of the green flags recruiters get excited to see, which can open doors or lead to unexpected offers. Niche skills Niche skills were cited by several as not only being valuable in and of themselves, but also being a great way to open otherwise closed doors. Even when the job description doesn’t call for your unusual ability or experience, it’s probably worth including them in your resume. “I’ll of course take into consideration the requirements as written in our current open listings,” said McClain, “as that represents the core of what we are looking for at any given time. However, I also try to keep an eye out for interesting individuals with skills or experience that may benefit us in ways we haven’t considered yet, or match well with projects that aren’t formally planned but we are excited about starting when we have the time or the right people.” Chidiac agrees that he takes special note of rare skills or very senior candidates on a resume. “We might be able to create an unseeable headcount to secure a rare talent. . . . I think it’s important to have that mindset, especially for niche areas. Machine learning is one that comes to mind, but it could also be very senior [candidates], like staff level or principal level engineers, or people coming from very strong companies, or people that solve problems that we want to solve at the moment, that kind of thing.” I call it the opportunistic approach, like the unusual path, but it’s important to have that in mind when you apply for a company, because you might not be a fit for a role now, but you might not be aware that a role is going to open soon. Sasaki pointed out that niche skills can compensate for an otherwise relatively weak resume, or one that would be bypassed by more traditional Japanese companies. “If the company you are applying to is looking for a niche skill set that only you possess, they will want to speak with you in an interview. So don’t lose hope!” Tailoring to the job description “I don’t think there’s a secret recipe to automatically pass the resume screening, because at the end of the day, you need to match the job, right?” said Chidiac. “But I’ve seen people that use the same resume for different roles, and sometimes it’s missing [relevant] experience or specific keywords. So I think it’s important to really read the job description and think about, ‘Okay, these are all the main skills they want. Let me highlight these in some way.’” If you’re a cloud infrastructure engineer, but you’ve done a lot of coding in the past, or you use a specific technology but it doesn’t show on your CV, you may be automatically rejected either by the recruiter or by the [ATS]. But if you make sure that, ‘Oh yeah, I’ve seen the need for coding skill. I’m going to add that I was a software engineer when I started and I’m doing coding on my side project,’ that will help you with the screening. It’s not necessary to entirely remake your resume each time, Chidiac believes, but you should at least ensure that at the top of the resume you highlight the skills that match the job description. Connections to Japan While most of this advice would be relevant anywhere in the world, recruiters did offer one additional tip for applying in Japan—emphasizing your connection to the country. “Whenever a candidate overseas writes a little thing about any ties to Japan, it usually helps,” said Chidiac. For example, he believes that it helps to highlight your Japanese language ability at the top of your resume. [If] someone writes like, ‘I want to come to Japan,’ ‘I’ve been going to Japanese school for the last five years,’ ‘I’ve got family in Japan,’ . . . that kind of stuff usually helps. Laine Takahashi confirmed that HENNGE shows extra interest in those kinds of candidates. “Either in the cover letter or the CV,” she said, “if they’re not living in Japan, we want them to write about their passion for coming to Japan.” Ho went so far as to state that every overseas candidate he’d helped land a job in Japan had either already learned some Japanese, or had an interest in Japanese culture. Tourists who’d just enjoyed traveling in Japan were less successful, he’d found. How important is a cover letter? Most recruiters had similar advice for candidates, but one serious point of contention arose: cover letters. Depending on their company and hiring style, interviewees’ opinions ranged widely on whether cover letters were necessary or helpful. Cover letters aren’t important “I was trying to remember the last time I read a cover letter,” said Clement Chidiac, “and I honestly don’t think I’ve ever screened an application based on the cover letter.” Instead, Mercari typically requests a resume and poses some screening questions. Chidiac thought this might be a controversial opinion to take, but it was echoed strongly by around half of the other interviewees. When applying to jobs in Japan, there’s no need to write a cover letter, Edmund Ho told me. “Companies in Japan don’t care!” He then added, “One company, HENNGE, uses cover letters. But you don’t need,” he advised, “to write a fancy cover letter.” “I never ask for cover letters,” said Axel Algoet. “Instead, I usually set up a casual twenty-minute call between the hiring manager and the candidate, as a quick intro to decide if it’s worth moving forward with the interview process.” Getting to skip the cover letter and go straight to an early-stage interview is a major advantage Algoet is able to offer his candidates. “That said,” he added, “if a candidate is rejected at the screening stage and I feel the client is making a mistake, we sometimes work on a cover letter together to give it another shot.” Cover letters are extremely important According to Sayaka Sasaki, though, Japanese companies don’t just expect cover letters—they read them quite closely. “Some people may find this hard to believe,” said Sasaki, “but many Japanese companies carefully analyze aspects of a candidate’s personality that cannot be directly read from the text of a cover letter. They expect to see respect, humility, enthusiasm, and sincerity reflected in the writing.” Such companies also expect, or at least hope for, brevity and clarity. “Long cover letters are not a good sign,” said Koji Hamane. “You need to be clear and concise.” He does appreciate cover letters, though, especially for junior candidates, who have less information on their resume. “It supplements [our knowledge of] the candidate’s objectives, and helps us to verify the fit between the candidate’s motivation and the job and the company.” Caleb McClain feels strongly that a good cover letter is the best way for a candidate to stand out from a crowd. “After looking at enough resumes,” he said, “you start to notice similarities and patterns, and as the resume screener I feel a bit of exhaustion over trying to pick out what makes a person unique or better-suited for the position than another.” A well-written and personal cover letter that expresses genuine interest in joining ‘our’ team and company and working on ‘our’ projects will make you stand out and, assuming you meet the requirements otherwise, I will take that interest into serious consideration. “For example,” McClain continued, “we had an applicant in the past who wrote about his experience using our e-commerce site, SolarisJapan, many years ago, and his positive impressions of shopping there. Others wrote about their interests which clearly align with our businesses, or about details from our TokyoDev company profile that appealed to them.” McClain urged candidates to “really tie your experience and interests into what the company does, show us why you’re the best fit! Use the cover letter to stand out in the crowd and show us who you are in ways that a standard resume cannot. If you have interesting projects on Github or blogs on technical topics, share them! But of course,” he added, “make sure they are in a state where you’d want others to read them.” What to avoid in your cover letter “However,” McClain also cautioned, “[cover letters are] a double-edged sword, and for as many times as they’ve caused an application to rise to the top, they’ve also sunk that many.” For this reason, it’s best not to attach a cover letter unless one is specifically requested. Since cover letters are extremely important to some recruiters, however, you should have a good one prepared in advance—and not one authored by an AI tool. “I sometimes receive cover letters,” McClain told me, “that are very clearly written by AI, even going so far as to leave the prompt in the cover letter. Others simply rehash points from their resume, which is a shame and feels like a waste. This is your chance to really sell yourself!” He wasn’t the only recruiter who frowned on using AI. “Avoid simply copying and pasting AI-generated content into your cover letter,” Sasaki advised. “At the very least, you should write the base structure yourself. Using AI to refine your writing is acceptable, but hiring managers tend to dislike cover letters that clearly appear to be AI-written.” Laine Takahashi and Sonam Choden at HENNGE have also received their share of AI-generated letters. Sometimes, Choden explained, the use of AI is blatantly obvious, because the places where the company or applicant’s name should be written aren’t filled out. That doesn’t mean they’re opposed to all use of AI, though. “[The screeners] do not have a problem with the usage of AI technology. It’s just that [you should] show a bit more of your personality,” Takahashi said. She thinks it’s acceptable to use AI “just for making the sentences a bit more pretty, for example, but the story itself is still yours.” A bigger mistake would be not writing a cover letter at all. “There are cases,” Takahashi explained, “where perhaps the candidate thought that we actually don’t look at or read the cover letter.” They sent the CV, and then the cover letter was like, ‘Whatever, you’re not going to read this anyway.’ That’s an automatic fail from our side. “We do understand,” said Choden, “that most developers now think cover letters are an outdated type of process. But for us, there is a lot of benefit in actually going through with the cover letter, because it’s really hard to judge someone by one piece like a resume, right? So the cover letter is perfect to supplement with things that you might not be able to express in a one-page CV.” Other tips for success The interviewees offered a host of other tips to help candidates advance in the application process. Recruiters vs job boards There are pros and cons to working with a recruiter as opposed to applying directly. Partnering with a recruiter can be a complex process in its own right, and candidates should not expect recruiters to guarantee a specific placement or job. Edmund Ho pointed out some of the advantages of working with a recruiter from the start of your job search. Not only can they help fix your resume, or call a company’s HR directly if you’re rejected, but these services are free. After all, external recruiters are paid only if they successfully place you with a company. Axel Algoet also recommended candidates find a recruiter, but he offered a few caveats to this general advice. “Many candidates are unaware of the candidate ownership rule—which means that when a recruiter submits your application, they ‘own’ it for the next 12–18 months. There’s nothing you can do about it after that point.” By that, he means that the agency you work with will be eligible for a fee if you are hired within that timeframe. Other agencies typically won’t submit your application if it is currently “owned” by another. This affects TokyoDev as well: if you apply to a company with a recruiter, and then later apply to another role at that company via TokyoDev within 12 months of the original application, the recruiter receives the hiring fee rather than TokyoDev. That’s why, Algoet said, you should make sure your recruiter is a good fit and can represent you properly. “If you feel they can’t,” he suggested, “walk away.” And if you have less than three years of experience, he suggests skipping a recruiter entirely. “Many companies don’t want to pay recruitment fees for junior candidates,” he added, “but that doesn’t mean they won’t hire you. Reach out to hiring managers directly.” From the internal recruiter’s perspective, Sonam Choden is in favor of candidates who come through job boards. “I think we definitely have more success with job boards where people are actively directly applying, rather than candidates from agents. In terms of the requirements, the candidates introduced by agents have the experience and what we’re looking for, but those candidates introduced by agents might not necessarily be looking for work, or even if they are . . . [HENNGE] might not be their first choice.” Laine Takahashi agreed and cited TokyoDev as one of HENNGE’s best sources for candidates. We’ve been using TokyoDev for the longest time . . . before the [other] job boards that we’re using now. I think TokyoDev was the one that gave us a good head start for hiring inside Japan. “And now we’re expanding to other job boards as well,” she said, “but still, TokyoDev is [at] the top, definitely.” Follow up Ho casually nailed the dilemma around sending a message or email to follow up on your application. “It’s always best to follow up if you don’t hear back,” he said, “but if you follow up too much, it’s irritating.” The question is, how much is too much? When is it too soon to message a recruiter or hiring manager? Ho gave a concrete suggestion: “Send a message after three days to one week.” For Chidiac, following up is a strategy he’s used himself to great effect. “Something that I’ve always done when I look for a job is ping people on LinkedIn, trying to anticipate who is the hiring manager for that role, or who’s the recruiter for that role, and say ‘Hey, I want to apply,’ or ‘I’ve applied.’” [I’ve said] ‘I know I might not be able to do this and this and that, but I’ve done this and this and this. Can we have a quick chat? Do you need me to tailor my CV differently? Do you have any other roles that you think would be a good fit?’ And then, follow up frequently. “This is something that’s important,” he added, “showing that you’ve researched about the company, showing that you’ve attended meetups from time to time, checking the [company] blogs as well. I’ve had people that just said, ‘Hey, I’ve seen on the blogs that you’re working on this. This is what I’ve done in my company. If you’re hiring [for] this team, let me know, right?’ So that could be a good tip to stand out from other applicants. [But] I think there’s no rule. It’s just going to be down to individuals.” “You might,” he continued, “end up talking to someone who’s like, ‘Hey, don’t ever contact me again.’ As an agency recruiter that happened to me, someone said, ‘How did you get my phone [number]? Don’t ever call me again.’ . . . [But] then a lot of the time it’s like, ‘Oh, we’re both French, let’s help each other out,’ or, ‘Oh, yeah, we were at the same university,’ or ‘Hey, I know you know that person.’” Chidiac gave a recent example of a highly-effective follow-up message. “He used to work in top US tech companies for the past 25 years. [After he applied to Mercari], the person messaged me out of the blue: ‘I’m in Japan, I’m semi-retired, I don’t care about money. I really like what Mercari is doing. I’ve done X and Y at these companies.’ . . . So yeah, I was like, I don’t have a role, but this is an exceptional CV. I’ll show it to the hiring team.” There are a few caveats to this advice, however. First, a well-researched, well-crafted follow-up message is necessary to stand out from the crowd—and these days, there is quite a crowd. “Oh my goodness,” Choden exclaimed when I brought up the subject. “I actually wanted to write a post on LinkedIn, apologizing to people for not being able to get back to them, because of the amount of requests to connect and all related to the positions that we have at HENNGE.” Takahashi and Choden explained that many of these messages are attempts to get around the actual hiring process. “Sometimes,” Choden said, “when I do have the time, I try to redirect them. ‘Oh, please, apply here, or go directly to the site,’ because we can’t really do anything, they have to start with the coding test itself. . . . I do look at them,” Choden went on, “and if they’re actually asking a question that I can help with, then I’m more than happy to reply.” Nonetheless, a few candidates have attempted to go over their heads. Sometimes we have some candidates who are asking for updates on their application directly from our CEO. It’s quite shocking, because they send it to his work email as well. “And then he’s like, ‘Is anybody handling this? Why am I getting this email?’,” Choden related. Other applicants have emailed random HENNGE employees, or even members of the overseas branch in Taiwan. Needless to say, such candidates don’t endear themselves to anyone on the hiring team. Be persistent “I know a bunch of people,” Chidiac told me, “that managed to land a job because they’ve tried harder going to meetups, reaching out to people, networking, that kind of thing.” One of those people was Chidiac himself, who in 2021 was searching for an in-house recruiter position in Japan, while not speaking Japanese. In his job hunt, Chidiac was well aware that he faced some major disadvantages. “So I went the extra mile by contacting the company directly and being like, ‘This is what I’ve done, I’ve solved these problems, I’ve done this, I’ve done that, I know the Japanese market . . . [but] I don’t speak Japanese.’” There’s a bit of a reality check that everyone has to have on what they can bring to the table and how much effort they need to [put forth]. You’re going to have to sell yourself and reach out and find your people. “Does it always work? No. Does it often work? No. But it works, right?” said Chidiac with a laugh. “Like five percent of the time it works every time. But you need to understand that there are some markets that are tougher than others.” Ho agreed that job-hunters, particularly candidates who are overseas hoping to work in Japan for the first time, face a tough road. He recommended applying to as many jobs as possible, but in a strictly organized way. “Make an Excel sheet for your applications,” he urged. Such a spreadsheet should track your applications, when you followed up on those applications, and the probation period for reapplying to that company when you receive a rejection. Most importantly, Ho believes candidates should maintain a realistic, but optimistic, view of the process. “Keep a longer mindset,” he suggested. “Maybe you don’t get an offer the first year, but you do the second year.” Conclusion Given the staggering number of applications recruiters must process, and the increasing competition for good roles—especially those open to candidates overseas—it’s easy to become discouraged. Nonetheless, Japan needs international developers. Given Japan’s demographics, as well as the government’s interest in implementing AI and digital transformation (DX) solutions for social problems, that fact won’t change anytime soon. We at TokyoDev suggest that candidates interested in working in Japan adopt two basic approaches. First, follow the advice in this article and also in our resume-writing guide to prevent your resume from being rejected for common flaws. You can highlight niche skills, write an original cover letter, and send appropriate follow-up messages to the recruiters and hiring managers you hope to impress. Second, persistence is key. The work culture in Japan is evolving and there are more openings for new candidates. Japan’s startup scene is also burgeoning, and modern tech companies—such as Mercari—continue to grow and hire. If your long-term goal is to work in Japan, then it’s worth investing the time to keep applying. That said, hopefully the suggestions offered above will help turn what might have been a lengthy job-hunt into a quicker and more successful search. To apply to open positions right now, see our job board. If you want to hear more tips from other international developers in Japan, check out the TokyoDev Discord. We also have articles with more advice on job hunting, relocating to Japan, and life in Japan.