The Application

Application Questions

While every company uses its own set of application questions, there are rules you can follow to provide great responses regardless of the question being asked.

There’s a trend where some companies don’t even ask for a resume or cover letter anymore and use only their application questions as the starting point for weeding out people who aren’t a good fit.

In this section of the workbook you’ll find:

  • A checklist of items you need to consider when writing up your responses.
  • Tips for standing (football fields 🏈) apart from other applicants.
  • Links to example questions and answers to help you see how these checklist items look in action.

Tip: Before you start writing up your responses, copy the application questions into a doc or your preferred note-taking app, so you don't lose any of the answers you're writing or accidentally submit the application form before you're ready. This happens more often than you might think, and it's not fun for anyone to deal with.

The Application Question Checklist

🔲 Alignment, alignment, oh and more alignment

Make sure you’re highlighting the skills and experience that you have that make you a good fit for this specific job at this specific company.

🔲 Show off your research

Show them that you dug into the details on the role and the company, and that you considered those when applying. It’ll show them that you actually care about this specific role and aren’t looking to land just any job fast.

🔲 Show your personality

Don’t be overly formal or use words and phrases that you would never say. Not even Sir Stick-Up-His-Butt has ever said something like, “Experienced and professional customer support representative with three years of experience in a dynamic work environment.” Just, no. Also, what does a “dynamic work environment” even mean!?!

Instead, show that you’re human. Be personable and show your personality. The type of companies you're applying for care about who they hire beyond just matching skills and experience. Go for friendly and professional, not a robot built in the 80's by a repressed, British earl.

🔲 Fully answer the question

Make sure to read the question carefully and answer everything that’s asked. If you don't, at best, the hiring manager will forgive the mistake but can’t use the information to get a good read on you (and they won’t be following up to give you another chance, unless the rest of your application is stellar and the question wasn’t a dealbreaker).

At worst, it looks like you were rushing or weren’t taking the questions seriously. And it may lead them to believe that you’d make the same mistake when responding to real customer questions.

🔲 Mention that you enjoy supporting customers

Too often candidates don’t make it clear that they enjoy supporting customers or find satisfaction in their work. Hiring managers want to know that you like support work because you’re saying that you want to do some version of it full time, often for at least 2-3 years.

🔲 Show off the skills that make you a good fit for remote work

In your application responses, resume, and cover letter, highlight the skills that hiring managers look for to gauge how well you’ll do working remotely. Those skills include:

  • self-management, self-motivated, can prioritize
  • takes initiative, action-taker, resourceful
  • enjoys learning, adapts well, flexible
  • great communicator, writer
    • This one gets highlighted in how you respond to application questions and how you write your cover letter. So you don't need to do anything about it now, it'll get covered in another section of the series.

🔲 Be clear and concise; don’t ramble

You will be reviewing and editing your application later. For now, if you’re on your third comma in a single sentence, use bullet points or find a good place for a period.

Your Resume

Before anything, check to see if the job you’re applying to even requires a resume. More and more remote companies are replacing the need for a resume with in-depth or targeted questions on their application.

When it comes to resumes, there are thousands of articles available to help you with everything from what social links to include to what font size works best for a specific ATS.

This section isn’t going to cover any of that.

There is only one thing that we will be focusing on. The thing that really makes a difference to hiring managers:

Does your resume show that you are a fit for THIS role at THIS company?

That’s it.

The part of your resume that does the heavy lifting on showing that is your work history, so we’ll mainly focus on that. The other area that can help is the summary statement, so we’ll spend a little time on that too.

Beyond that, if you have questions about your education, skills, or anything else about your resume, check out the Resume Tools & Resources section below.

Below you’ll find a step-by-step guide, templates, and examples to help you with updating your:

  • Work history (does the heavy lifting 💪)
  • Summary statement (catches the hiring manager’s attention 😮)
Work History Update

Here’s how you’re going to turn those bullet points on your resume into increasingly excited head nods from hiring managers no longer losing their will to go on. (Look at you saving someone’s sanity while scooping up a fabulous remote job. Niiice.)

Step 1

Make a copy of your resume. New role, new resume.

Step 2

Pull up your list of alignment points and the job post with the description of the role.

Step 3

Now’s the fun part. Go through the bullet points in your work history and update them to highlight the alignment points you identified and any qualities or skills you have mentioned in the job description. If there are bullet points you left off that align with the role, this is the time to add them back in.

Here’s an example of what that looks like in action.

Job Description
(click to expand)
Notes on the Company, Role, and, Alignment
(click to expand)
Resume Work History
(click to expand)
Original resume work history

Customer Success Manager
Pink Hippo, January 2018 - Present

  • Supported customers via Zendesk, averaging 100+ tickets a week with a 1.8 business-hour median response time.
  • Investigated, diagnosed, and troubleshot customer-reported issues utilizing tools such as Fullstory to escalate specific details to the engineering team.
  • Worked to promote client retention, growth, and satisfaction by maintaining positive customer relationships.
  • Created a process for gathering positive customer reviews and exceeded the first month’s goal of 100 reviews.
  • Educated customers on using the product and walked them through every step of onboarding.

Tier 2 Customer Support Agent
Red Rhino, January 2017 - October 2017

  • Responded to an average of 20+ tickets per hour when while maintaining a high CSAT score.
    Replied to questions in the community’s Facebook Group within an hour.
  • Triaged and resolved email requests from students, parents, and teachers. Averaged 500+ tickets per week.
  • Assisted in training new team members and provided them with guidance on handling complex problems.
  • Monitored and helped manage four social media groups by answering questions, providing access, and taking care of any other issues that arose.
Updated resume work history based on the job description

Customer Success Manager
Pink Hippo, January 2018 - Present

  • Consult customers on getting the most value from the product by understanding their use case and using product expertise to guide them towards their goals.
  • Investigate and troubleshoot technical issues, using tools such as Fullstory to resolve problems independently.
  • Collaborate with the product team to advocate for customer input and engineering teams to resolve complex technical issues.
  • Created a process for gathering positive customer reviews to give new users real examples of how they can use the product and exceeded the first month’s goal of 100 reviews.
  • Average 100+ tickets a week in Zendesk with a 1.8 business-hour median response time while balancing different customer needs, changing support volumes, and continually learning how our customers can leverage new features.

Tier 2 Customer Support Agent
Red Rhino, January 2017 - October 2017

  • Triaged and resolved email requests from students, parents, and teachers. Averaged 500+ tickets per week while maintaining a CSAT score of over 90%.
  • Assisted in training new team members and provided them with guidance on handling complex problems and providing creative workarounds.
  • Monitored and managed four social media groups by answering questions, providing access, and handling any other issues that arose within an hour.
  • Proactively brought in account managers when customers were nearing account limits and worked with account managers to recommend new product additions for customers.

Step 4

Now pick out the bullet points that don’t seem to align with the role you’re applying for.

Review each one to see if there is anything you missed that does align with the role or company. Consider whether they:

  • Highlight a skill that would help you in the new support role even if you used/learned the skill in a non-support role.
  • Highlight your experience in an industry or company type (like B2B, B2C, SaaS) that aligns with the company you want to work for.
  • Highlight a skill that you could use as you grow in that role. For example, the job description may not mention anything about creating and editing videos, but you have those skills and know that they can help with creating support resources for customers.

After your review, if you still have any bullet points that don’t align, remove them. Yep, take them right out.

Remember, they are still on your original resume, and you can reuse them if they are relevant for a future role. But right now, those bullet points are going to hurt you more than they help you.

Step 5

If your resume feels light now because you haven’t had a lot of customer-related roles or you removed a lot of irrelevant bullet points, then there are a few things you can do:

Multiple roles, same company

If you had multiple roles at the same company with different responsibilities, list those out separately.

For example, let’s say you spent three years at a company and you started as a junior support rep. Then two years in, you became a team lead coaching other teammates and managing the queues. Then you can list both of those positions on your resume. Here’s what that could look like:

Gold Tiger Inc., Austin, TX

Product Support Team Lead (January 2019–Present)

  • [mention your promotion/role change]
  • [That awesome thing you did for your team that people still talk about]
  • [The skill you’re proudest of and wield like a pro]
  • [That thing you did every day to ensure customers stuck around]

Product Support Specialist (January 2018–January 2019)

  • [The cool skill you learned to do that made customers go, “What?! You rock!”]
  • [That empathetic thing you did that turned a customer into a fan]
  • [The recap of all the work you did every month to help customers—with a smile and saint-level patience]

You might be missing some experience/skills (or underselling yourself)

If you think that all you offer is experience with answering dozens of phone calls and emails every day, you are dead wrong!

There is a difference between answering a question and...listening to someone, empathizing with their struggle, providing a thoughtful and creative solution to their problem, and following up a day or two later to see if that did the trick.

There is a difference between answering a phone call and...patiently letting someone vent, empathizing with their problem, asking them questions to understand the cause of their problem, suggesting a solution, waiting on the phone to confirm the solution fixed the issue, and reassuring them that you and your team are available to help ease their anxiety and concerns when they need it.

And that’s just the tip of the iceberg.

Don't doubt the immense value that you offer. Give yourself the credit you’ve rightfully earned.

Summary Statement Examples

The summary statement is right at the top of your resume so you don’t want to waste that valuable real estate. It’s an opportunity to show hiring managers how you’re different by:

  • Customizing it for the role you’re applying to (this is easier to do than you might think)
  • Highlighting your biggest accomplishment(s) right away, so they aren’t missed

Below are three example summary statements so you can see how the templates look in action. The comments in [ ] are there to clarify what’s working in the summary and why.

Example #1

Empathetic and self-motivated customer support professional with 2+ years of experience focused on helping customers understand and leverage the value of a product for their specific needs. Eager to help Green Llama Co. extend its already excellent customer experience to more customers by thoroughly understanding a customer’s needs and customizing each solution accordingly. Was promoted to the first Onboarding Specialist role at Purple Lions because of my ability to design and present creative solutions that customers were excited to implement.

[Notice that nowhere in that statement did we quantify how many tickets we worked on or what our CSAT score was. You can make an impression without numbers, especially when you focus on what’s most important to a company for the role they are hiring for. This company was looking for someone who could use deep product knowledge to generate creative and personalized solutions for each customer. So that’s what the applicant was trying to highlight.]
Example #2

Adaptable and resourceful customer experience leader with 7+ years of experience working to improve every point at which a customer interacts with a brand. Excited to help with Yellow Moose’s mission to empower entrepreneurs to build more successful businesses using automation by advocating for and executing data-driven projects that improve and scale the customer experience.

  • Implemented a process for creating and promoting high-quality knowledge base articles in half the time that resulted in a 20% increase in article views and 10% fewer support emails.
  • Developed, tested, and launched the use of an automated chatbot for capturing important details upfront about a variety of technical issues which resulted in those issues being resolved 4 hours sooner (25% faster).
  • Led and coordinated an initiative to grow customer focus across the company by sharing customer stories that showed how each team’s and individual’s contributions led to the specific successes customers were enjoying.
[This applicant was excited about the company’s mission and was able to mention that while still highlighting how they would be an asset to the company. This company was looking for a leader who had previous success in scaling support and customer resources using data. So the applicant focused on highlighting the projects and accomplishments that were in line with those needs. The company also wanted someone who could help maintain a sense of customer focus throughout the company as it continued to grow, and that’s where the last bullet point comes in.]
Summary Statement Templates
Replace everything in [ ] with your own details and make sure to remove all the [brackets] before saving the final version of your summary statement.

Shorter summary for those with less work experience (1-2 positions/titles or less than 5 years of experience)

[Strong soft skills that align with the role/company][your job title] with [x] years of experience [quick overview of your experience aligned with the role/company]. Eager/excited to help [company name][what you want to help the company achieve and how you want to do it]. [your key accomplishment(s)].

Longer summary with bullet points for those with more work experience (More than 2 positions/titles or more than 5 years of experience)

[Strong soft skills that align with the role/company][your job title] with [x] years of experience [quick overview of your experience aligned with the role/company]. Eager/excited to help [company name][what you want to help the employer achieve and how you want to do it].

  • [Key accomplishment 1]
  • [Key accomplishment 2]
  • [Key accomplishment 3]
Resume Templates

If you don't have a resume already or your resume isn't setup to be easily readable and scannable, then check out these resume templates:

To use the templates, you'll need to be logged into your Google or Gmail account and you'll be immediately prompted to make a copy of the template.

If you want a resume template that you can add more sections to or you can format while keep things readable, check out my favorite free resume builder:

Out of the dozens of resume builders I’ve tried, this one’s my fave because it’s actually free, you can store multiple resumes, and their formatting is clean, modern, and easy. Plus, you don't need to change a lot of the default options.

Resume Tools & Resources

There are thousands of articles and tools to help answer any questions you might have about putting together a resume. A lot of the advice out there is outdated or doesn’t apply to remote companies with a great culture, because they hire differently than most companies (that’s how they build awesome companies).

The good news is that there are websites out there sharing great advice and providing helpful tools. Below is a list of the resources that generally offer advice that will help you create a resume that will help (not hurt) your chances at an awesome remote company.

Your Cover Letter

Before anything, check to see if the job you’re applying to even requires a cover letter. Some remote companies are replacing the need for a cover letter with more in-depth or targeted questions on their application.

If a cover letter is required or you don't see any application questions asking you about why you're a good fit for the role or why you're interested in the role, then submit a cover letter. You want to make sure you have the chance to explain why you'd slay in this role.

Lots of articles mention how cover letters don’t matter or aren’t often read, yadda, yadda, yadda. Here’s the thing, for companies that care about the person they are hiring beyond just matching qualifications, knowing why you’re a great fit as a human is critical.

The good news is that thanks to the research you did and your list of alignment points, writing a custom cover letter can be a fun game of fill in the blank.

Below you have multiple cover letter examples and a cover letter template to help you write a cover letter that will get you noticed for all the right reasons.

Cover Letter Examples
Example #1

Details: Customer support role; a company with a platform for creating and selling sustainable products

Hello Idina,

I can’t say enough how excited I was to see the Customer Advocate job posted at Blue Palm. I’ve been buying sustainable products for years and truly appreciate that you’ve built a platform to bring more sustainable products to the world. I also really like the honest and goofy vibe that the company conveys. I, too, am a huge Keanu Reeves fan (whoa). Add to that how much you value transparency and honest feedback, and Blue Palm seems like the kind of company where I’d be excited to go to work every day.

I’ve been happily supporting customers with technical products for over three years, and I would be thrilled to be a part of helping your customers create their own sustainable products using your growing platform.

What, specifically, would I bring to Blue Palm as your newest Customer Advocate?

  • A dedication to creating memorable customer experiences  — In my support roles at Red Frog and Green Moose, I helped customers with everything from basic technical troubleshooting to complex product setups through email and chat. My approach of leading with empathy, clearly understanding and resolving the source of a question or issue, and following up until an issue was fully resolved, resulted in a consistent 97% satisfaction rate. It also led to customers repeatedly requesting to work with me.
  • Experience working with the product team for continuous improvement — In my role at Green Moose, I created a process for more easily sharing customer feedback with the product team. That improved their ability to prioritize the features and UI improvements that would have the greatest impact on customers. I also represented customers and the support team in weekly meetings with the product team to provide insights on customer feedback.
  • Experience in creating scalable customer resources — Every week, I used the insights gained on where customers were struggling with the product to create dozens of videos, articles, and guides for our knowledge base and website. I was impressed with the customer videos and walkthroughs I saw in the Blue Palm forums. I’d really enjoy helping to create walkthroughs for the customers in industries that are not yet covered.
  • A passion for sustainable products — I still remember the first pair of sustainable sneakers I bought. They were made from self-regenerating bamboo and recycled plastics, and were nothing like what I had expected. That first pair wasn't just my introduction to sustainable products. It also sparked a passion for helping communities all over the world and for the future of our planet.

I believe my successes in creating stellar customer experiences, advocating for customers internally, and my passion for sustainability would serve Blue Palm well. I would love to discuss the value I could add in more detail as your next Customer Advocate. Thanks so much for your consideration, Idina. I hope to speak with you soon!

Example #2

Details: Onboarding specialist role; online education company for kids

Hello Gregory,

With each word I read about your mission at Orange Cricket, I found myself enthusiastically nodding my head and thinking how much I wish your company existed when I was growing up. While I didn’t have that option, I’m making it up for it now by taking a couple of online classes every year because I’m a firm believer in “always be learning”. With a mission like yours and your dedication to your team’s learning and growth as well, it’s hard not to be excited about the Onboarding Specialist role.

I’ve been supporting customers and sales teams for two years at a SaaS company, and a busy queue of questions and calls is my jam. I would be thrilled to be a part of your mission to help kids and their families get the most out of your programs.

What, specifically, would I bring to Orange Cricket as your Onboarding Specialist?

  • Experience with a high-volume day while building trust with customers — In my sales support role at Purple Lion, I respond to about 60 emails and handle about 5-10 calls per day. Whether I’m emailing someone in the morning or on a late afternoon call, I make sure that I take care of every question and issue the customer has. And I read between the lines so that I can also take care of what they didn’t ask about but will keep them from being successful later.
  • Ability to maintain high standards without supervision  — I’m currently part of a flat-structured company where everyone is expected to manage themselves and deliver high-quality work. Thanks to my systems-focused approach to work, I can stay organized while juggling multiple customer issues and internal requests without missing the important details.
  • Focus on being valuable to the team as well — While I find a lot of joy in turning a frustrated customer into a happy and relieved customer, I also enjoy making work easier for those on my team. My love of systems and automation means that I’m always on the lookout for ways to improve existing processes or to add in automation that allows us all to provide customers with a better experience.

I believe that my passion for your work and for learning, my ability to build trust through dependable and high-quality work, and that I can manage my work myself would serve Orange Cricket well. I would love to discuss the value I could add in more detail as your next Onboarding Specialist. Thanks so much for your consideration, Gregory. I hope to speak with you soon!

Cover Letter Template
Replace everything in [ ] with your own details and make sure to remove all the [brackets] before saving the final version of your cover letter.

Hello [hiring manager],

[Strong opener with a personal story or details about why you’re interested in this job. This is a good place to talk more about the alignment of values, mission, culture, and growth. The majority of cover letters are about skills and experience, so by starting with your alignment in other areas, you’re already showing how different you are.

In the end, include a line that mentions a quick overview of your support experience and your excitement about the job. This will be a good lead into the details of your experience. This part shouldn’t be longer than 1-2 concise paragraphs.]

What, specifically, would I bring to [company name] as a [role you’re applying to]?

  • [Experience/skill that aligns with the role #1] — [Two to three sentences about your experience and skills that directly ties to how you would be of value to the company you’re applying for. Since this is the first bullet point, make sure this covers the skill or experience that you think makes you the best fit for the role.].
  • [Experience/skill that aligns with the role #2] — [Two to three sentences about your experience and skills that directly ties to how you would be of value to the company you’re applying for. This should cover the next most impactful skill or experience that makes you a good fit for the role].
  • A history of accelerating brand affinity for nonprofits — [You get the point by now, right? Of course you do. Now finish this section off!].

I believe [most important alignment point #1], [most important alignment point #2], and [most important alignment point #3] would serve [company name] well. I would love to discuss the value I could add in more detail as your next [role you’re applying to]. Thanks so much for your consideration, [hiring manager]. I hope to speak with you soon!

Second-guessing yourself?

You’ve added in the ways you’re aligned with the job and company. You’ve highlighted your skills and experience. You got a little personal and resisted the urge to delete the whole cover letter. But there’s a lingering feeling that maybe you oversold your abilities.

Sure, you wrote a bunch of support articles for your help desk. NBD. Lots of support folks write articles, right? And, yes, you spend a little extra time walking new customers through how to set up their first marketing campaign. They’re new and need the extra help. Anyone would do the same. It’s nothing special...

First, not every single support person writes articles, spends extra time with certain customers, or does any of the things you do.

Second, doing those things IS a big deal. Writing knowledge base articles means that you help more customers and make it easier for them to get answers more quickly. Spending that extra time can be the difference between a customer loving your product and giving up after a few weeks and going to a competitor.

The work you do is immensely valuable. Period.

Don’t sell your hard-earned experience, skills, and yourself short. Now, read through your cover letter again and make sure that you’re not downplaying your worth. Being confident in your skills and experience is helpful to the hiring manager who’s trying to find someone like you who can help their customers be successful. Breathe that in until you believe it.