Using AI to apply as Happiness Engineer

Since I posted that we’re hiring in Woo Happiness, my LinkedIn inbox has been flooded with people seeking advice on how to apply, wanting to share their résumé with me, and asking why they didn’t make it through to a next round.

While I understand these questions, they ironically also often pose a red flag for me: we want people to work autonomously, to read procedures carefully and follow them, and to be self-improving. When someone asks me in a direct message how to apply when I’ve just a shared a link to the application process, you likely won’t be a good fit for our team.

So, what would some of my advice be for applying? When I joined Woo before the Automattic acquisition over 10 years ago, AI and LLMs weren’t a thing yet, so I had to do the research myself. One of my biggest pieces of advice would be to use the available AI tools as your personal assistant throughout the process.

Research

Start by doing research. The job posting has many details, but both the Automattic website and the rest of the web contain a bunch of insightful information that could help with the application process. Find out what the company values, both in the content, but also in the format of the application.

I quickly asked ChatGPT:

I’m planning to apply as a Happiness Engineer at Automattic. What are the things that they seem to care about a lot? What are mistakes I shouldn’t make?

As the head of support, I can confirm that ChatGPT’s reply was to-the-point.

So think of questions you may have, or challenges you can encounter along the way, and let a bot help you prepare for those.

Apply

While I would recommend writing your own application, and trial replies, it would be a missed opportunity to not use AI tools to tweak it.

A few suggestions:

Many of us use grammar tools like Grammarly and LanguageTool. Use those, not just for your grammar, but also to compare with the style of the company.
Have ChatGPT check your application with the values of the company. Beware of course for hallucinations.

Improve

Both during the application process but also should you be rejected, use AI to help analyse where you could improve.

For example, I would give feed the rejection letter in Claude.ai and compare it with some of the tests I’ve written. I would then ask for advice on where I missed the ball.

Note: At Automattic, we take privacy and security very seriously, don’t share any personal and identification information with an AI tool.

Your thoughts?

What are some of your questions and suggestions on how to use AI tools during application processes?

Also, we’re hiring!

Interested in working for a company with more than 20 years of experience with remote or distributed work? We’re hiring!

November 20, 2024

2–3 minutes

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Comments

3 responses to “Using AI to apply as Happiness Engineer”

November 20, 2024

Marjorie

I had someone recently call me on my personal cell phone twice at 7am; send me 2 text messages an hour later when I didn’t respond; and DM’d me on LinkedIn that same evening.

I think this person thought he was being “proactive” and “out of the box” and “persistent”, which on its face sounds like qualities we look for in an Automattician, and yet on balance, the impression I’m getting is someone who:

has zero boundaries (how did this person get my personal phone number, and why did he think it would be appropriate to call me twice at such an early hour?);
didn’t do his research on the job listing (I’m not at all involved in hiring the role he’s asking about);
and has a shaky-at-best sense of what’s appropriate and not appropriate in a professional business environment (persistently texting a woman he’s never met, has never engaged with, who has never given him her personal phone number, is a BIG RED FLAG. All caps for those in the back)

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November 22, 2024

Iqbal

It’s indeed concerning if you have shared a link to the application process but people are still asking how to apply for a job at that place.

It seems that not everyone who has a desire also has the will to take action and find out what they want. I sometimes experience this too, where someone asks how to apply for a PhD scholarship that I am also pursuing, even though the application link has already been shared across various national media. In fact, pursuing a PhD requires the enthusiasm to read information (which is already available everywhere).

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November 20, 2025

Yukay

Thank you

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