Kaylie Boogaerts

I was quite cheeky in the cover letter that I sent to Checkly. I knew I needed to pique the interest of whoever read my application because I wanted a role they weren’t actually hiring for! I invite you to come on a journey with me, where we go back in time and I lay bare the secrets of how I landed a dream job that didn’t even exist when I applied!

Have you heard about the law of attraction? To me, it means that when I want to achieve something, I put it out there and I tell people about it. By doing that, I consciously or unconsciously start working towards that goal and eventually, my wish will come true. So when I started looking for a new job, I told as many people as I could. I told them exactly what I was looking for: a remote-first tech startup with an international team, looking to grow sustainably, where I would be the first People person in the team.

Lo and behold, an ex-colleague of mine (hi Niklas!) sent me the link to Checkly’s Executive Assistant job with a few People Ops responsibilities. He said he almost didn’t send it to me because he knew it didn’t quite fit the role I was looking for, but the company looked cool and the product was great. Because they were looking for someone to handle finance tasks, reporting, travel coordination, managing calendars and expenses etc, I also almost didn’t apply. Other than the actual position, the company seemed to fit exactly what I was looking for, so I took a chance.

Take a chance, be bold, and highlight your accomplishments


Here are my actual cover letter and CV from when I applied to Checkly in June 2021, and what I think made Checkly take a chance on me. 



This is probably the only time I was ever so bold and cheeky in a cover letter. I’m generally a humble person, but if I was going to convince them to hire me for a role that didn’t exist, I wanted to  grab their attention from the start.

I then highlighted my accomplishments in a similar environment, showing I have the necessary experience to build up the People function and grow the team at Checkly.

Here I showed the traits that make me thrive in a startup environment: I know exactly what I want, am proactive and have an entrepreneurial spirit. If I was writing this cover letter right now, I’d write about how the combination of being part of a team and consulting enables me to learn so much faster and more consistently.

That was my entire cover letter! Bold and specific to what I was looking for and what I thought Checkly needed. 


There’s something that feels very vulnerable about publishing your CV from 2 years ago like this, but here we go!

As someone who’s seen probably tens of thousands CVs in her life, if not more, here are a couple of tips that I personally find important:

Go for a layout that makes it extremely easy for the receiver to find what they’re looking for. That includes having your most recent experience at the top and least recent experience at the bottom. Same goes for your academic history.

Leave out irrelevant information. Even though I learned a lot during my student job selling roasted chicken, that’s not a fact that’s going to convince the hiring manager to hire me. If I were to look for a new job now, Checkly would be at the top of my CV and I’d leave out my experience as an Account Manager because it’s no longer relevant.

When describing your responsibilities, focus on what you’ve accomplished and add as many data points as you can. (See: yellow highlights)

If you have short tenures, add context as to why that is in your CV already to proactively take doubts that a recruiter or hiring manager might have. (See: blue “*1”)

Don’t only write the last or first title you had at a job, but make sure to show your progression and growth in your CV. (See: red “*2”)

How I made sure I’d love working at Checkly

I had a clear idea of what type of environment I thrive in: tech startup, remote-first/fully remote, sustainable team growth, building people topics up from scratch.

On top of that, I also understood my personal values and the values I seek in leadership: fairness, transparency, ownership, trust and caring for diversity and inclusion.

During the interview process, I asked targeted questions to see if Checkly and its leadership would match all of these wants and needs such as:

How would you describe their leadership style?

How do you collaborate across time zones?

If interviewing for a job was only about the questions you ask the interviewer, it’d be easy! You have to also answer questions. Here are my top 3 interview tips:

Research the company. Make sure you understand what the company does and how your background could benefit the company.

Be your authentic (best) self. Being genuine and authentic in your interview process makes it easier for interviewers to relate to you. On top of that, if you get the job and you were authentic during the interview process, you know that you can also be your authentic self at your new job. At least for me, this takes away a lot of new job stress!

Prepare examples of your work and impact. Think of some examples of initiatives and projects that you’ve worked on (or led!) that show impact or how you deal with difficult situations. The closer they relate to the role, the better! My mind usually goes blank if I have to think of examples on the spot. Pro-tip: practice laying out these examples in a structured and concise way to avoid rambling during the interview.

A day after I sent out this application, I received an invite for the first interview with the CEO. Eight days after the first interview, I had met the entire founder team, rewrote the job ad to fit the new role, received an offer and signed my contract. 🎉

As I was writing this blog post, I wondered if what I thought landed me my job at Checkly actually matches the perception of our CEO Hannes. What better way to find out than to ask, right? Here’s what he said:

“It was clear that People operations and someone helping us establish a culture and processes in this area were missing, though it wasn't the most crucial role then. At least, that's what I thought when I kicked off the hire for an Executive Assistant to cover operations. So what convinced me?

In the cover letter, the first sentence was 100% on point "you probably already know that I'm overqualified for this position." Yes, Kaylie was clearly overqualified. BUT she had seen scale in a startup that maybe had a similar culture to what I was trying to achieve with Checkly. I want to hire future leaders who have seen the scale and bring experience in their areas. So, the cover letter + CV convinced me to have a conversation - though I was skeptical if I could make Kaylie successful at Checkly then.

The first conversation was fantastic. It was clear that:

We could benefit from having Kaylie on board while scaling the org from 8 to 30.

Kaylie was hands-on enough to wear multiple hats for some time if needed. I asked her to amend the job description as a way to test this.

She could help me to push diversity! We were 100% man-only at that time and I was a bit nervous that I would have a hard time implementing the thinking about diversity later at scale.

My gut told me that working with Kaylie would be easy because of a cultural fit, but also because she had previous startup experience.

Last but not least, Kaylie’s former colleague - a user of ours - also thought she was a good fit. (Sometimes, these little signals make a huge difference.)”

I joined the Checkly team as a People Ops Manager in July 2021. Now almost 2 years later, I’ve been promoted to Director of People and still love working at Checkly.

I can’t promise you your dream company is going to change up a role for you, it just might not be the right time. But I encourage you to take a leap, stand out with an amazing application, and show them what you’re made of and what they’re missing out on if they don’t take you on board. You never know what might happen!

How I Landed My Dream Job – That Didn’t Exist

Detect

Communicate

Resolve

Monitoring as Code

Developers

Resources

Community

How I Landed My Dream Job – That Didn’t Exist