Staff & Training

5 Tips For Applying To Jobs At UpKeep

Ryan Chan


Almost every hiring manager knows hiring is tough. With hundreds of applicants and resumes, it’s no longer simply about having the skills and background listed in a job description, but being able to stand out from the crowd.

Often times the actual hiring process is quite opaque to the applicant. Job seekers are often left asking questions like… “Did someone even READ my cover letter that I spent hours writing? Why did I get rejected? Are they still hiring for this position at company X if the opening is 3 weeks old? What else can I do to express my genuine interest in this company, even if that means being open to multiple positions?”

That was exactly me when I was applying for my first job coming out of college. I remember writing dozens of cover letters only to be left in the dark…. forever without a response. At times it felt like it was just dropping my name into the resume lottery and simply wishing for the best.

Reflecting on this lack of transparency is what led me to write this post. In an attempt to take out any mystery to the process, you can find out exactly what we look for in applicants here at UpKeep, the general timeline to our hiring process, how to prepare and more  – all below!

Without further ado…. Here are 5 tips when applying for a job at UpKeep.

Hint! If you’re reading this article, you’re already one step ahead of the game 🙂 Don’t be afraid to mention you read it!

1. One of the most important questions on every job application we ask is “Why UpKeep and why this position?”

This is our more modern approach to a cover letter and your response is the very first thing we screen for. Our promise to you is that we read each and every single response regardless of your prior experience and resume.

We’re all guilty of it…. and I am too. We’ve all sent a generic cover letter, copying and pasting the same one to the 30 different jobs and the 10 different positions. However, to truly stand out from the crowd, we want to see that you really know what UpKeep is all about, who we are, and what the position entails.

To help make this simple for you, we’ve done away with requesting traditional cover letters and instead ask you directly, “why?” Your response doesn’t need to (and shouldn’t) be paragraphs long. We want to hear your enthusiasm about working at UpKeep, your excitement for joining a startup environment, interest in learning about the the maintenance industry. Anything that has you applying to this position should shine through in your answer!

Here’s an example of a bad cover letter (it was one of my first ones coming out of college. Is that embarrassing or what?!)

And here’s a great one


2. Tailor your resume to highlight your experience for the position you’re applying for.

After reading the cover letter, our hiring managers then screen through the resume.

A reminder that our hiring managers read dozens of resumes a day. Your prior experience at other companies probably spanned work across multiple departments and you may wish to add details on every responsibility you’ve ever had into your resume.

At the end of the day, the longer a resume is, the better, right? Wrong! You can read our job description and know exactly what our hiring managers are looking for. If you have experience with any of our skills or requirements listed in the job description, don’t be afraid to add our language to your resume directly. This highlights your resume to show us that you’ve got the skills and experience for what we’re looking for at UpKeep (and that you’ve read our job description thoroughly!)

For example, if you’re applying for an operations role, highlight all of the areas where you’ve done that before! Here’s a great resume for our operations manager position.

3. If you don’t have the skills, requirements, and experience, don’t hide it (and definitely don’t lie!) Just tell us… why is now the time to learn? How have your past experiences prepared you to take on this new challenge?

Often times, having working professional experience is not only about the skills developed over time, but also about “knowing what the position entails.”

For example, if you’re looking for your first position in sales as a Sales Development Representative and you’re coming from a customer success role, you may worry that you don’t have the exact past experience in a sales-related position. Since you’ve had a customer facing role previously, you can easily explain how you’ve done this task before in a slightly different fashion. It’s important, however, that you mention how you see this role being different than your last! Sales takes a very unique personality, one that’s quite different than someone in CS, and vice versa. Be ready to own up to the new challenges that would be ahead of you in your new position, and explain that you know how you’d need to grow if selected.

The “Why UpKeep” question on the application is the perfect place to include this.

4. During the interview, know UpKeep’s core values and be prepared to answer questions on how you’ve previously applied those values at your previous jobs:

    1. Gritty resourcefulness
    2. Customer commitment
    3. Dedication to progress

5. Download UpKeep and be prepared to talk about the product, the mission, and our customers.

Our product and customers are what the entire company revolves around. Knowing the product is essential for every single position here at UpKeep!

*Bonus tip – be sure to come prepared with interesting questions to ask us during your interview!

We take note of all our candidates’ questions to make sure our interview process is as informational as possible.

Ready to apply? Start your next journey at UpKeep here!

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