The 8 Biggest Mistakes to Avoid When Applying For a Remote Job

Advice on landing remote roles from hiring experts at Doist, Buffer, InVision, Timely, and Toggl.

Illustration by Yin Weihung

There’s a quiet revolt brewing against traditional office jobs.

People are tired of open office plans, unreasonable commute times, and the struggle of doing their best work within the limiting confines of 9 to 5.

The rise of remote work and fully distributed teams has been a direct response to the pains of the modern workplace and a growing desire to achieve work-life balance. Perks like extravagant offices are no match for what people truly want: flexibility.

3.9 million U.S. employees work from home at least half of the time, which is up from 1.8 million in 2005. While a flexible schedule is a huge benefit for almost anyone, for stay-at-home parents, military spouses, primary caregivers, and those with disabilities, remote work is often one of the only opportunities to develop a meaningful career.

There’s just one snag: How do you land a remote job when you’re competing for a single role alongside hundreds, or even thousands, of applicants from across the world?

Application pool for the “Your Position” role at Doist

Since joining Doist in January 2018 as our People Operations Manager, I’ve reviewed over 7,000 applications for roles spanning design, marketing, customer support, and software development.

However, even small changes to the way you approach your remote job search will help you stand out. I’ll be highlighting where you may go wrong on your quest for a remote role with advice straight from those actually doing the hiring.

The Remote Hiring Process

Before diving into common remote job hunt mistakes, let’s look at the process as a whole.

Here’s what the hiring process looks like at Doist:

  1. Initial screening — Resume and Cover Letter Review.
  2. Interview 1 — Interview with someone you would be working with
  3. Test Project and Assessment
  4. Interview 2 — Interview with someone else you would be working with
  5. Interview 3 — Interview with our COO
  6. Job Offer

This is similar to processes at other remote companies like Buffer, Gitlab, Zapier, and Automattic.

While a comprehensive hiring process might feel daunting, try to view it as multiple opportunities to stand out. While we’ll touch upon best practices throughout the entire funnel, we’ll pay close attention to mistakes to avoid before the initial screening phase. Why? This is typically the only stage most applicants reach.

Mistake #1: Sacrificing quality for quantity

It’s tempting to submit your resume to every opening that remotely (pun definitely intended) fits your experience. Unfortunately, this method results in low-quality applications that are unlikely to stand out. Instead, determine the key criteria you’re searching for in a remote job and focus on preparing a few high-quality applications that you’re proud to submit.

Go deep on a few companies instead of wide on many companies.

When you’re searching for an exciting new opportunity, it feels counterintuitive to shrink your net instead of widening it. But it’s often dedicated effort on a few priorities that wins out over divided attention on various options.

This is also the case when pursuing various open positions at a single company. It’s acceptable to apply to multiple roles at the same place if you feel qualified for each one. However, it’s a red flag when we see candidates apply for 4+ positions. I’ve observed applicants simultaneously submit applications to be software engineers, translators in multiple languages, and support specialists. Don’t do this. Instead, hone in on your experience and the value you can bring to a team and communicate that clearly throughout your application.

Going deep on a few companies means you can dedicate extra time and effort not only to your application but additional networking and contact as well. If there’s a company you’re excited about, go the extra mile to build connections with people there beforehand. Find opportunities to organically interact with their team members on social media or reach out and ask for an informational interview. Demonstrate that you’re genuinely interested in what they do and how you can be a part of it. Not only does this put you on the company’s radar, but it also provides you with inside information that can give you a leg up as you’re going through the hiring process. This isn’t a tactic you can meaningfully duplicate with fifty companies. Start with five and go from there.

Mistake #2: Not doing enough research before applying

“So, why do you want to work here?”

Long before you need to answer this question during an interview, you should be able to answer it for yourself. The best way to do this is through extensive research.

  • What are the company’s values?
  • Do they have a core mission?
  • What are their goals over the coming years?
  • What’s the company’s origin story?
  • Who is the hiring manager for this position?
  • Do they have a positive team culture?

Dig into a company’s website, blog, and social media accounts. Go deep and check if the company’s founder has been featured on podcasts where they speak to their company’s mission or values. Set up a Google Alert for the company and its founders.

Glassdoor gives you an idea of what employees really think of the company.

Websites like Glassdoor can also help you see what current and former employees at a company like and dislike about working there. Apps like Blind can provide insights into a company’s culture as well as their recruiting and interview process. While you shouldn’t base your entire opinion about a company on individual reviews, they can provide additional insight and help you craft a compelling cover letter or raise questions during the interview phase.

For instance, candidates applying to Doist sabotage their chances of being considered for a role when they express something in their application that directly contradicts our values. Writing “I can work 12+ hours for you in a day. And weekly 84 hours and I’ll work 365 days” isn’t a strong value proposition when maintaining balance is central to our values and culture.

Vanessa Radich is the People Experience Lead at Timely. They’ve been a distributed team since day one and have experimented with their own version of remote work they call “#timelylife”. They’re deeply passionate about their product and look for new team members who can share in that excitement. Candidates conducting research before applying, to truly understand the company they’ll be joining, is one of the first clues that a potential hire will thrive at Timely.

I am always really impressed when candidates know where we’re at as a business — in terms of where our product sits in the market, our target customer, how many years we’ve been in operation and the number of staff we have. Most people do little to no research, so even just getting a few basic things right makes a candidate really stand out!

— Vanessa Radich, People Experience Lead at Timely

Your research should also include finding out what “remote” means for each company:

  • Do team members work from home on occasion but are expected to go into the office most of the time?
  • Will you be required to be online during specific windows of time?
  • Will you have to track your hours?

These details matter. Consider them when researching whether a job is a good fit for you.

Magda Cheang, EMEA International Recruiter at InVision, suggests that research is imperative when applying for a remote role. Despite being over 700 strong and an enviable model for building a highly valued remote company, they want candidates to go beyond the surface and explore the company and its products.

“Applying for a distributed company shouldn’t be any different from a traditional, office-based company. In fact, I’d say you have to do more research and showcase you are interested in the business model, product, and company culture, and not make it seem that remote working is your main driver. Remote working is more of an approach and value that a company has, but is not the main aspect.”

— Magda Cheang, EMEA International Recruiter at InVision

After completing your research, you may discover that a company isn’t quite what you were searching for. That’s okay! You haven’t wasted your time, you’ve simply strengthened your criteria and will be better suited to identify a remote position that checks all the boxes.

Mistake #3: Disregarding the cover letter requirement

Companies typically request a resume and cover letter. Your resume tells the company what you’ve done in the past.

Your cover letter should demonstrate the following:

  1. Why you’ve applied
  2. What you’ll do for the company in the future

Required or not, always write a cover letter.

The “why” behind your application is a key detail to remote companies. When a company is hiring someone to work remotely, they are looking for someone they can trust. For a distributed team, where there isn’t a physical location to help facilitate the development of organizational culture, it’s important that everyone shares mutual values and is motivated by the company’s mission. Without a cover letter, a hiring manager has no way of knowing who you are or why you are applying.

At Doist, not including a cover letter is a deal-breaker. Before even looking at role-related skills, we look to a candidate’s cover letter to learn why they are applying and what they can bring to the team. Not including a cover letter sends us the message that a candidate hasn’t spent any time learning about us. That may not always be the truth, but when a candidate hasn’t put in effort upfront it’s hard to believe they’ll be committed once hired.

Cover letters aren’t just about learning who you as a candidate, they help remote companies get a sense of your written communication skills. In remote companies where asynchronous communication is key, you interact with your team primarily through writing.

Courtney Seiter is the Director of People of Buffer, one of the pioneers of remote work. She notes that “one of the biggest factors in standing out as a strong remote job candidate is the ability to communicate well and proactively.”

At Buffer, we find that great candidates generally show a high level of communication skill in a number of ways. One way is by matching their tone to that of the job description and our other online content, like blog posts. Buffer tends to communicate in a casual, friendly, and open way. When we see candidates model this communication, it’s generally a sign that they’ve done a bit of research to become familiar with the way we talk with our customers and community, which feels really great. They’re already one step closer to feeling like a part of the team!

— Courtney Seiter, Director of People at Buffer

Mistake #4: Writing a generic cover letter

A generic cover letter is nearly as ineffective as no cover letter. Don’t submit cover letters where the only thing you change is the name of the company. If a cover letter could be reused, mostly unchanged, for multiple applications, it’s generic.

Making a handful of changes to your application isn’t quite enough to impress a hiring manager either. Many candidates fail to write a memorable cover letter because they waste it on providing “a quick resume summary” or highlighting a selection of their past experiences without making a connection to the role and company they’re applying to. These types of cover letters are redundant and don’t present a full picture of the candidate. If you feel the need to summarize your resume, then chances are high that your resume needs some tweaking.

A cover letter is also a strong indicator of how much time a candidate has spent preparing their application. It’s a great opportunity to demonstrate your knowledge of a company beyond what was included in the job description. When writing a cover letter, aim to showcase a deep understanding of a company’s mission, why you want to be part of it, and the value you hope to add.

To avoid submitting an unmemorable cover letter, ask yourself the following questions:

Ensure your cover letter is as original as you are.

If you can answer “yes” to all of these questions then your cover letter is on track to stand out.

I find that a personalized cover letter quite hard to come by these days! A friendly tone with some genuine reasons as to why the role at Timely appeals to them goes a long way with me.

— Vanessa Radich, People Experience Lead at Timely

Cover letters also play an important role if you decide to submit an unsolicited application. In these cases, a company isn’t actively hiring for a particular role or may not even know that this role is needed. For this scenario, a cover letter needs to explain what value the proposed role would add while still providing insight into you as a candidate.

At Doist, we receive a lot of unsolicited applications through “Your role” (which you can find on our jobs page). Many of these submissions are resumes accompanied by messages such as “let me know if you have a job for me”. This is an incredibly passive approach to job hunting that simply doesn’t work. However, some unsolicited applications include some of the best cover letters we read because they are written by candidates who care about what our company does and feel compelled to apply without a position available. Although we can’t always offer a role to these candidates right away, their motivation doesn’t go unnoticed.

In place of cover letters, some companies ask applicants to answer a series of application questions instead. Doist recently adopted this practice in response to our global applicants who have expressed cover letters were not a common practice in their countries. We found that asking specific questions allows us to create a more equal entry point for candidates. We’re able to learn more about them upfront and see how effectively they communicate, while minimizing the stress that comes with the open-ended task of writing a cover letter.

In fact, we removed the cover letter field entirely. This has also helped us read and respond quicker to the high volume of applications we receive because we don’t have to hunt for indicators in cover letters.

When reviewing candidate responses there are three types that we see very often:

  1. Too short: These responses are only a few sentences long and don’t give us much insight on the candidate. The lack of depth suggests that the candidate didn’t spend very much time preparing their application.
  2. Too general: These responses are ambiguous and could have possibly been reused from other applications. When we read these, we tend to question whether the candidate actually took the time to learn about us.
  3. Too long: These responses are sometimes as long as, or shockingly, longer than a typical cover letter and tend to lack focus. They often sacrifice quality for quantity.

The best way to approach answering application questions is to imagine that you are answering them in a live interview. You want to provide a detailed, specific, and well-developed answer that shows that you’ve taken the time to prepare and can communicate effectively.

A very simple example that we see frequently is when we ask candidates to share a few of their top strengths. Many candidates simply list three skills and end their responses there. However, imagine you were asked this question in an interview? You wouldn’t just list your strengths and end your responses, you would go into more detail about how you put those strengths into action or what it took to develop them.

These are your opportunities to make your application stand out in a meaningful way. Of course, quality responses alone will not necessarily land you an interview, but they’ll draw closer attention to your application.

Don’t underestimate the value that a strongly written cover letter or thoughtfully answered application question adds. When applying for a remote job alongside candidates around the world, It’s likely that there are many candidates who are just as qualified as you. However, personal and original cover letters or application questions could provide just the edge you need to stand out as someone that a company needs to meet.

Mistake #5: Overemphasizing your desire to work remotely

There’s no denying the appeal and benefits of working remotely. It’s okay to acknowledge that you enjoy remote work, but there’s a fine line between doing this and making it clear that your main motivation is to “work from home” or “travel the world”. Remember, at the end of the day you’re still applying for a job; it just happens to be remote.

While stressing your desire to travel or work from home may send the wrong message, demonstrating your ability to work independently and framing it around what a flexible work arrangement will allow you to bring to the company is always a plus.

In the content of their messaging, standout candidates focus not just on their experience and background but also bring home how those experiences relate to the position they’re applying for to make them a strong choice. For example, many folks mention that they have experience working remotely or a passion for remote work as the way of the future. The next step that really stands out is to share what remote work allows you to do. Are you more focused? More creative? More communicative? How will those qualities display themselves in the work and lead to great outcomes for the company you hope to work with?

— Courtney Seiter, Director of People at Buffer

Vanessa from Timely offers similar advice:

We place importance on folks having a genuine reason to want to work remotely. It’s best when there’s an obvious benefit to them that is unlocked by being able to work remotely. Usually, that’s a passion or a commitment outside of work, but it could also be that it suits their working style. On the flipside, if a candidate is talking about “making it work” or “there shouldn’t be any problems” that tends to indicate it won’t be a good fit. We look for people that are excited about working remotely, either knowing from experience or excited by the prospects. It’s also really important that people are able to work autonomously and be self-motivated.

— Vanessa Radich, People Experience Lead at Timely

If you’ve previously had experience in a remote role, draw from that and explain that you have the skillset to thrive without supervision. If you’ve never had a remote job, demonstrate that you have strong communications skills, the ability to work autonomously, and strong personal responsibility, through other non-remote experiences. In this case, emphasize any experience with freelancing, leading work projects, working on personal projects, or starting your own venture.

Mistake #6: Letting interviews be one-sided

Congrats, you landed an interview! You’re one step closer to landing that remote job you’ve wanted. Of course, like any interview you’ve had in the past, you’ll be asked a series of questions that span various topics relating to your past experience and future ambitions.

Interviews are one of the best opportunities throughout the hiring process to leave it all on the table. Demonstrate your knowledge of the role and the company. Hone in and share the skills you possess. Let your interviewer know you’re perfect for the role.

Showcase that you are someone who has a good work ethic, are transparent and over-communicative. All of these skills are necessary to be successful in this distributed model. It’s not about how you work, but how you show what you’re working on and the impact of your work. Here at InVision, we care about impact and not the hours that you work. Don’t mistake motion for progress. It’s a wonderful way to ensure you can design your life and work in the way that you want but companies still want to see the impact of what you do.

— Magda Cheang, EMEA International Recruiter at InVision

While resumes and cover lets can be incredibly telling, finally meeting face-to-face (or Zoom Window to Zoom Window!) will be the first time a company gets a glimpse into your personality and what you’re like to work with. If a company is seeking out strong collaborators and team members with humility, actions like speaking over your interviewer or being condescending will be a red flag.

Evelin Andrespok is the HR Manager at Toggl, a fully distributed team. They’re not willing to sacrifice a strong culture of respect, even for the most talented individuals.

While we look for the best people in their fields, there is no place for know-alls or primadonnas at Toggl. We are looking for team players who add value to each other’s work, not compete for the spotlight.

— Evelin Andrespok, HR Manager at Toggl

It’s easy to feel like you’re in the hot seat, but remember that interviews are a two-way street. They also allow you to better determine whether the company and the role are a good fit.

As a candidate, prepare a set of questions to ask your interviewer about the company and the role. If you use a generic set of questions during every job interview, it’s time to retire that list. Generic questions, like a generic cover letter, aren’t going to make you stand out as a candidate. Generic questions also tend to have answers that you could (and should) have found by doing thorough research.

Examples of bad questions to ask during an interview:

  • What does your company do?
  • How quickly can I get promoted?
  • Who are some of your competitors?

In general, good interview questions demonstrate that you’ve done your research and are seeking a deeper understanding of the company and the role. These questions could be prompted by details you’ve come across in a company’s blog, social media updates, or interviews that employees have done. Referring to specific sources that have prompted your questions can add additional credibility to your interest in the company.

Examples of good questions to ask during an interview:

  • What are some qualities that have allowed others in a similar role within the company to thrive?
  • Is there a particular pain point within the company that this role should address?
  • Is this role open in order to replace a previous employee or to grow a team?
  • What does good and/or bad performance look like on your team?
  • I read an interesting article in your blog about x, y, or z. Can you elaborate on how you’re currently addressing this issue at the company?

Consider asking questions that respectfully challenge your interviewer and speak to the tough issues the company is facing. Asking these types of questions can give you insight into what the company culture is like and how willing employees are to reveal areas of growth within their company. Asking these types of questions also shows your interviewer that you don’t shy away from difficult conversations.

Mistake #7: Doing the bare minimum

The hiring process offers several opportunities to share your personality, how you think and approach problems, and how you would fit in a team. Remote companies often look for people who will not just fill a role, but go above and beyond. It’s not uncommon to look for people who have the potential to take a role to new heights that previously weren’t envisioned.

How do you show that you are able and willing to take this kind of initiative before you get the job?

Of course, it begins with making an above-average effort on your application. If you do the bare minimum, such as attaching a resume and a generic cover letter, then you’ve already sent a message that you’re only willing to invest minimal effort into tasks.

Be creative and show you have done your research and are truly passionate about the company! We had a candidate recently who used the InVision tools to create his resume, that definitely got him noticed and we fast-tracked his application. It turned out he was a wonderful fit with the team.

— Magda Cheang, EMEA International Recruiter at InVision

Going above and beyond sends a clear message that you’re invested, even before you get a job offer. At Buffer, applications typically ask a few open-ended questions that go beyond the standard “cover letter” material (such as questions that relate to specific company values and how candidates might relate to them). These questions are optional, but as Courtney Seiter puts it, it’s “puzzling” when applicants choose to leave them blank. “Every field is an opportunity to help a hiring team learn about you, root for you, and imagine you doing awesome work with them,” says Seiter.

But it’s not just about saying all the right things; it’s also about what you actually do. At Doist, every candidate is asked to complete at least one paid test task that is related to their role as part of the hiring process. This is another opportunity to go above and beyond what is requested. How can you think bigger about the task that you’ve been given? In addition to completing the task, you might offer additional suggestions or an implementation plan. These suggestions might not necessarily work for the company, but they will demonstrate your thought process, creativity, and willingness to think beyond the immediate task. Don’t waste these little opportunities to demonstrate the value you can bring to a team.

“The goal of trial work and interviews at Toggl is to test a candidate’s skills, but also to see whether they are open to new experiences and able to learn new things, especially on their own, without being told to do so.”

— Evelin Andrespok, HR Manager at Toggl

Mistake #8: Handling rejection poorly

Unfortunately, only one candidate ultimately gets the job. After all the time spent applying it can be frustrating to receive a rejection email, or worse, no response at all. Some candidates choose to respond distastefully and, in doing so, ruin their chances of being considered for future openings.

Instead of getting frustrated or responding in a way that you might regret, use the opportunity to ask for feedback. Not every company is able to respond to individual feedback requests, but you have nothing to lose by asking. At worst, you won’t receive a response. At best, you could receive valuable feedback that will help you when applying for a new opportunity or applying again at the same company down the line. Asking for feedback also shows that you have a growth mindset.

“Feedback is a gift and is really coming from a positive intention — trying to help you improve, showcase your gaps in knowledge or weaknesses. This way you can understand yourself more, reflect, and work to improve your skills. Sometimes it’s down to other candidates being stronger, so you shouldn’t take the decision too personally. Getting rejected will also help you build resilience and perhaps understand the timing isn’t right for you to get that job you applied for.”

— Magda Cheang, EMEA International Recruiter at InVision

At Doist, several of our current team members were initially rejected but were proactive in turning the rejection into an opportunity for learning and growth. Panos Tsamoudakis, a member of our design team, found himself in this very situation when he applied to join Doist back in 2016.

Panos turned an initial rejection into a job offer at Doist by asking for feedback.

After receiving the rejection, Panos kindly requested feedback. His proactive and persistent response to rejection earned him a second chance, and after going through the hiring process, he got the job (and is still going strong at Doist today). It doesn’t always work out this way, but if he hadn’t asked for feedback, he might never have gotten a second chance.

If you find that you’re receiving rejection after rejection, take time to assess why that might be.

  • Are you applying for roles that are far outside of your experience or skill set?
  • Is it clear from your application why you’re applying?
  • Are you consistently making the same mistake from one application or interview to the next?

Requesting feedback can help you identify any issues in your remote job search approach.


I hope you take away valuable advice from this article on how to stand out while applying for a remote job.

Here’s what I hope you didn’t take away:

  • “I’ll never be able to get my application noticed by a remote company”
  • “Applying for a remote job is far too time-consuming”
  • “I’ll probably get rejected, I shouldn’t even bother”

This tidbit of information should help quell your fears: the vast majority of applicants don’t adhere to a single one of the tenets we describe throughout this article. We receive hundreds of applications with no cover letters and countless submissions that don’t make any mention of what we do as a company.

Take it from from someone who followed this advice:

Several years before applying to join Doist, I had a very clear vision of what I wanted in a job. I was looking for an HR role that would leverage my background in Psychology, Human Resource Development, and interest in technology and productivity. I wanted to join a company that had strong values and would see me and others as people, not just “resources”. It was my goal to do meaningful work that would positively impact people. I had been using Todoist (our flagship productivity app) for years before I applied, but it wasn’t until I learned about the company behind the product that I started to see that we shared a lot of mutual values and common goals — I knew I wanted to work there.

By chance, an HR internship opened towards the end of my program. By the time I eventually applied, I had been closely following the company for at least two years. I read Doist’s Ambition and Balance blog, listened to podcast interviews featuring Doist team members, and continued investing in my personal and professional development. This made all the difference. By the time I applied, it felt natural for me to communicate my motivations and how I would bring value to the team. I didn’t have it all figured out, and I couldn’t have until I joined the company, but applying with a deep understanding upfront was instrumental in landing my current role.

Following the advice in this article may not immediately land you the job of your dreams, but it will put you in the top percentile of applicants and help you rise above the noise.