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Learn How to Land A *Dream* Remote Job from The Best

Practical Tips from Top Hiring Managers at GitLab, Buffer, Hotjar, Dropbox, Microsoft, The Hustle, Moonpig, Zapier & Automattic

Penélope Wan 🟣🟠
9 min readDec 14, 2020

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As a Digital Product Manager based in Taiwan, where even tech companies are slow to embrace working from home due to cultural reasons, I’ve fancied the possibility to work remotely but never know how to best pursue.

I participated Remote Career Success Week with an intention to conduct business research on Arc, got really inspired by personal stories shared by the speakers, who are also experienced hiring managers building remote teams at GitLab, Buffer, Hotjar, Dropbox, Microsoft, The Hustle, Moonpig, Zapier and Automattic, on how & why they got their first remote jobs, so I use this article to document my takeaways on the steps I can take toward the goal.

10 Speakers of Remote Career Success Week 2020 hosted by Arc

Takeaway Highlights

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  1. Mind Your Intention Of Working Remotely And Show It
  2. Build A Strong Online Presence To Display Who You Are
  3. Demonstrate You Are Capable To Excel Even Without Prior Experience With Remote Work
  4. Cultivate Yourself To Be Suitable For This Work Style
  5. Pick The Company With Values That Are Aligned With Yours

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  • What Did Other Participants Care to Know About Remote Working?
  • Useful Resources
Screenshot of the ongoing event on Hopin (Photo credit: Remote Career Community Facebook group by Arc)

1. Mind Your Intention Of Working Remotely And Show It

As many things in life, you need to identify the “WHY” behind each decision to find clarity that would eventually guide you with mindful actions towards fulfillment — same for “remote working”.

For me, it’s that total ownership in how I could structure my days that appeals me to explore this work style that is opposite from what I’m comfortable with, so that I would have time and flexibility for something valuable to myself.

Such as replacing long commuting hours with quality time spent with family and close friends beyond borders, or any activities to build a strong foundation for my physical health and wellbeing.

“Start With Why” explained in the Golden Circle proposed by Simon Sinek

Speakers explained (and I agree), if your answer is simply to travel around the world, which is also a great reason as it pleases you, you won’t be able to differentiate yourself much from other candidates applying for the same position.

Know your own values, think whether the way you work really fits the backbone, and display them in your cover letters and applications.

2. Build A Strong Online Presence To Display Who You Are

By setting up a blog sharing thoughts or a work portfolio and putting it out there, you create a pull for others to approach you with new opportunities, versus you actively searching as a push.

Established platforms, such as LinkedIn, Twitter, Quora, Slack, are recommended for professional networking by sharing curated content on a regular basis. Key is to show your mindset and how you’re engaging with the industry, examples of content could be:

  • Briefing on books or articles you recently read by experts in your field
  • Insightful conversations you found interesting over Podcasts
  • Inspirations from a conference or panels you just attended in a picture with enthusiastic fellow attendees in the background☺️
Visions of the Future, a fictional travel poster series by NASA’s Jet Propulsion Laboratory, which reminds us that “You can be an architect of the future.”

Almost every speaker mentioned about “Passion Projects.”

It can be something inspired from design jams with others, crazy “re-design” works for existing products in the market, or even going further: find someone on CoFoundersLab with complimentary skills to yours, such as a technical programmer, tell your story and inspire others to work with you!

Other helpful tips include:

  • Generally speaking, real world works are more favored than proof of concept.
  • For “Passion/Hobbit Project” — Choose at least one (after all, life isn’t all about work), something you’re really interested that would show who you are, and keep the idea small enough that is accomplishable but still solves a real problem.
  • For “Portfolio” — Quality over quantity. However, have at least 2 case studies that can demonstrate your comprehensive thought process in design or product development, even if your work is simply to carry out decisions made by others.

*Updates on Dec 16:
Codementor recently launched
DevProjects, a community that allows junior engineers work closely with senior developers and mentors on web development, mobile apps, and automation/tools, to start building their own portfolio.

3. Demonstrate You Are Capable To Excel Even Without Prior Experience With Remote Work

In-house professionals who have never had experience in remote working might find it hard to get started……

Image Credit: Wachiraphorn on Getty Images

Luckily, there are common traits and soft skills that the speakers underlined most of us might have already mastered:

OVER-COMMUNICATION

Unlike at office, where you can easily make up excuses passing by your colleague’s table to check in on the status of ongoing projects. Nor can’t you gauge unspoken ideas from body language through a video conference.

This is THE #1 MOST IMPORTANT trait to ensure alignment in understanding, that all speakers couldn’t emphasize on anymore. Period.

CONCISE

Simplify all your communication to express ideas concisely, written or oral. Example: always writing a preview for a document to let people know why they should spend 20min reading it.

SELF-AWARE

Know how you work would impact others, and respect other’s time. Example: flexibility to adapt your work schedules for others based in different time zones.

AUTONOMOUS

Combine different experiences from various jobs to exemplify. It could be a project when you needed to manage multiple vendors located remotely across several time zones, yet successfully delivered expected results on time.

FAMILIAR WITH COLLABORATION TOOLS

I, as a Software Product Manager, have used the following tools for my day-to-day work in product design and development:

Figma: collaborative interface design
Trello: project management
JIRA: issue and project tracking in software development
Confluence: collaborative wiki to share knowledge
Slack / Telegram: team communication
Notion: all-in-one workspace for documentation
XMind: complex information management
Zoom / Google Meet: video conferencing
Google Drive: file management
World Time Buddy: time converter for distributed teams
GitHub: software development (mainly for engineers)

4. Cultivate Yourself To Be Suitable For This Work Style

Image Credit: 5 New Routines to Create Work From Home Boundaries by Adobe

Self-discipline is very crucial to stay productive when working remotely. This is what your potential hiring manager would definitely ask about, to further evaluate whether you’re capable to perform as an individual as well as to collaborate with a distributed team.

This also echos the last takeaway: 3. Demonstrate You Are Capable To Excel Even Without Prior Experience With Remote Work, so be sure you’re constantly working to improve it throughout your daily life.

Speakers suggested to figure out your own morning rituals to kick off a productive working day! Acts like getting dressed, eating breakfast, working out, then grabbing coffee before starting to immerse yourself in a pleasant environment that yields the most productivity.

Create boundaries that help you to maintain good mental health habits. Never, ever skip any routine.

5. Pick The Company with Values That Are Aligned with Yours

Well, this (philosophically) is the end and the beginning.

One speaker, Megan Murphy, VP of Product at Hotjar, shared her real life experiences in very delightful juicy conversations, about how taking your personal values into account can help guide to achieve fulfillment toward this holistic goal with grounded tactics.

Get a Remote Job by Sticking to Your Values by Megan Murphy at Hotjar

There is really a lot worth covering (I highly recommend those who missed the interview to watch the recording), but to briefly summarize:

Step #1: Know your values.

You’ve got to first ask yourself what your values are. Recognize it when you are not in conditions that are aligned with your values, and then make sure that is actually the most important thing in choosing where you go next.

Try writing them down or consulting people whom you trust, who sound like they are aligned with your values. Moreover, make sure your values are your values, because sometimes we have the opportunity where we have the impression by other people and other factors in life.

There is no silver bullet or imaginary Oprah moment where it becomes clear out of a sudden, all you can do is to keep digging deep relentlessly and be constantly mindful with that pivot and change when it comes.

It’s a long game, as the speaker put it.

Step #2: Screen companies (values) for what you want and what you don’t.

Once you’ve recognized what your values are, don’t be afraid to ask questions accordingly even in very early interview or any round with the recruitment team before you go on to more mature stage of interview processes.

Let’s say, if “build trust with transparency” is important to you at work, then ask questions to the interviewer, who might possibly be your future up-line manager, like:

  • Can you give me an example of how your team exhibited transparency last week (a specific time)?
  • When were you transparent with the team you lead about a strategic decision made by the executives last week? What was that about? How did that go?

Things like that would give you early indicators. Even if it sounds like a dream job on paper, but then in the real talk in the real discussions, you’re not seeing consistent evidence that your values are really present and embodied there.

Then you need to start making conscious decisions in where you’re going that really speaks to you.

Image Credit: Emotional Competency

What Did Other Participants Care to Know About Remote Working?

The conference took place from 10am until 5pm at Pacific Standard time (2am to 9am in Taipei, for me), so I assumed they aimed to reach professionals based in the US.

Majority of the audience worked in Engineering (36%), Design (26%), Product (14%) and Marketing (8%).

About “Remote Working”, they expressed:

  • Companies that provide info about cultures, salary transparency and perks/benefits would interest them more to consider a remote position.
  • Having opportunities to learn new skills/grow professional and being part of a great team with an inclusive culture is important.
  • Time management, project management & client managements are the top skills to advance for them feel confident in remote success.
  • More work flexibility (hours/location) but smaller package (paycheck/benefits) is much preferable to larger salary but less flexibility.
  • Higher interest in full-time remote jobs than freelance part-time ones.
Screenshots of the polling to engage with online audience

Useful Resources

About “Arc”
A hiring platform, powered by Codementor, helping leading tech companies and startups that aim to efficiently grow remote teams, recruiting quality vetted developers from all around the world.

Remote Career Success Week 2020 event banner

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Image Credit: Digitalvision by Martin Puddy | Getty Images

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Penélope Wan 🟣🟠
Penelope Wan’s Product Journal

Product Professional | UX Design Enthusiast | Avid Solo-Backpacker | Passionate about creating awesome experiences across the end-to-end development lifecycle