JOB HUNTING

My Reverse Job Application

Jackie Guan
8 min readOct 16, 2020
Two notebooks on a coffee table
Photo by Thought Catalog on Unsplash

Jan 2021 update — I am pleased to say that I have accepted a full-time product offer and yes - my reverse job application helped me get the role. I will be leaving the article up for inspiration and archiving purposes.

Why❔

It’s been a few months since I’ve begun interviewing for product manager roles and my sister Joyce encouraged me to try a less conventional approach to job hunting and let the jobs come to me. Having a background in chemical engineering and transitioning from being an engineer to a product manager, writing the reverse job application was also a better way to tell my story.

Full disclosure — this version was heavily inspired by Julie Pagano’s page, my sister’s page and of course the original reverse job application.

When🗓️

Soon! I am happy to start conversations and interviews now. But recognizing that these chats take time, I am aiming for a start date around end of November or even early 2021.

Where 🍁

I am currently based in Toronto, Canada, and this is where I would like to stay. I am mostly interested in remote positions, but I am not opposed to going back to a socially distant office 2–3 days a week either. I deeply miss the office, and I’m excited for the pandemic to be over, so I can go back to building in-person relationships.

About me 👩🏻

Check out my LinkedIn or resume for an overview of my work experience, education, and more.

I am a product manager with experience in building digital products in urban transportation, AI chatbots and e-learning. In the past, I was a project engineer for almost 8 years in the mining industry designing innovative manufacturing processes. While the transition to product management is new, my ability to manage projects and people, understand complex technical concepts, and build interesting things is not. My favourite thing about going to work is collaborating with a team to solve interesting problems.

My latest project was building a mobile app for urban cyclists with a few friends called Arrive. Having been an urban cyclist myself for almost 10 years, I noticed that none of the conventional cycling apps seemed to address safety, which is arguably the #1 concern for current and would-be cyclists on the road. Wanting to make urban cycling safer and more accessible for everyone, I decided to work with some friends to make an app to change that. Over 3 months, we were able to survey 130 people with a $0 budget, launch a website, build a demo app for alpha users, and put in an entry for the Slingshot Pitch competition.

In the past, I spent 8 years as a project engineer in a small company wearing many hats such as managing R&D projects, developing large-scale multi-million dollar engineering construction projects, and writing government grant applications for extra funding. Though I was an engineer, it was also during this time where I honed my soft skills, such as the ability to manage different stakeholder groups, collaborate with cross-functional teams, juggle multiple priorities and build a presentation for any audience. The company was subjected to the whims of the market and our projects were often delayed, but I was always known as the person who could help you out and get things done, regardless of the circumstances.

In my spare time, I like learning new things and I am currently learning French at an intermediate level for fun! To keep my product skills sharp while I look for my next role, I’m currently building another side project with a group out of New York called Seguro Project. We are building an AI chatbot to help domestic violence organizations manage call volumes. It is a project that warms my heart and something I plan on continuing with even after securing full-time employment.

Having worked in complex environments with regulations and other constraints in place, I’m not opposed to working in a similar space again. The thing I’m most looking forward to though is working with a team to build products that will deliver value and improve experiences for the end-user.

What I’m looking for 🔎

  • Good people — I believe in the ‘Ubuntu’ philosophy — that I am who I am because of the people around us. ‘Good’ to me means teams and people who have a collaborative mindset, and can show kindness and respect to its members and each other.
  • Interesting problems — Coming from an engineering background, I love working in different problem spaces! In the past, I worked on inventing a new method for making lithium sulfate for the battery market, building a new Learning Management System (LMS) for kids to build soft skills, and I’m currently working on an AI chatbot for domestic violence shelters.
  • Work/life balance — I believe people do their best work when they are well rested, and this applies to me as well. While I’m not opposed to occasionally (once or twice a month) working a bit later to meet deadlines, working 60+ hour per week is just not for me.

Location 🌎

I am primarily looking for organizations working ±3 hours from Eastern Standard Time for ease of collaboration and work overlap. You do not have to be based in Canada, but you do have to be set up to support remote employees based there in accordance to Canadian law (e.g. vacation leave, sick leave, family leave).

Size 📏

I am flexible about the size of the organization, as I am most excited about building products and growing with the company. Having said that, I want to focus on being a product manager and would prefer being in a team with some structure eg) processes, staff, etc already in place.

Type of work 💼

I am primarily looking for Product Manager roles.

More specifically, I am looking for product roles that:

  • Will make a positive impact to user’s experience — Whether that is B2B or B2C, I’m really interested in building products that users will enjoy and will have a positive impact to their lives.
  • Include the ability to work closely with my team to solve problems — I love team work, collaboration and working together to build something together.
  • Include the ability to make and give presentations — I love building slide decks and I’m really looking forward to doing this in my next role.

While this is not an exhaustive list, I do think it highlights some of the key things that I’m looking for in my next role.

Culture ⛩️

Here are some of the things that are important to me in the culture where I work.

  • Collaboration — Did I mention that I really like working in teams? Haha. On a serious note though a good, collaborative team environment to me means that people work with each other and not against each other, and knowledge and help is shared at every level.
  • Communication — Managers and teammates set expectations for each other and the team and communicate on a regular basis on how these goals and expectations are going. If things are not going well, rather than escalating, honest discussions are held for possible solutions and next steps. Leadership are open to ideas and change from any one in the company and feedback is regularly exchanged at every level.
  • Work/life balance — I know that I work my best at ~40 hours a week. I don’t mind occasionally (once or twice a month) staying late or doing a bit of time on weekends but I’d really like to keep overtime at a minimum.

Pros 😃

The following things will excite me about your organization. I’m easily excitable.

  • A flexible work schedule — My main work hours are between 9–5 ET, but I appreciate flexibility when the occasion calls for it
  • 20+ days of paid vacation
  • 10+ days of sick leave
  • Retirement contribution/matching program
  • Support for employees for things like professional development, and extra-curricular activities (e.g. gym, learning fund etc)
  • Support for home office setup and other recurring home office costs (e.g. internet).
  • Your organization is in the health, travel, EdTech or FinTech field.
  • You have a scrum master/agile coach on your team
  • Your organization uses French in some ways, either with clients or you have offices in French speaking regions — I’ve been learning French on the side for 2 years now and I love it! I would love to be in an organization where I can practice with my coworkers

Cons 📉

Below are things that will make me less excited about your organization. They’re not dealbreakers, but seeing them will make me sigh out loud.

  • A very long and opaque hiring process — I get it, it costs a lot to hire and the impact of finding the wrong person is high but I think it’s fair to give timelines for candidates on what to expect and if the person is not succcessful — give them actionable feedback to improve for the future.
  • No established performance appraisal systems — Even if your company is very small, I still think it’s important to have regular discussions on how I’m doing and steps for progression and improvement.
  • Vague job descriptions like “Rock Star PM”, “work hard, play hard”. We all want to be rock stars but what does that mean really?
  • Lack of an HR department — people issues happen all the time and having processes in place to deal with them makes things smoother for all of us.

Dealbreakers 💔

The following are dealbreakers. Your organization is not going to be a good fit.

  • Requirement for travel — I’m not comfortable getting on an airplane any time soon.
  • Heavy over-time requirements outside work hours — For example- working on weekends more than once a month, or working past 7 PM everyday of the week when you started at 9AM.
  • Your company has zero women or visible minority employees.
  • Your company does not believe in climate change — The environment and combating climate change is an important part of my personal values.
  • Zero or low quality health care coverage — Canada provides wonderful healthcare but there are still gaps in our system and seeing the dentist is important to me.
  • Heavy drinking culture — I don’t mind socializing at a bar but I’m just not one to drink heavily all the time.

Contact me 📧

Congrats, you’ve made it to the end! Does all of this sound interesting to you? Great! You should contact me if you meet all of the following criteria:

  • You work for the organization you are contacting me about. Ideally you are a hiring manager, product manager, or someone who works closely with the team (e.g. designer, developer).
  • You’ve read the post and think your organization would be a good fit for me and vice versa.
  • Your organization is hiring now or in the near future.

Please contact me via email and include the following:

  • The name and location of your organization.
  • A link to your website and a brief description of why we would be a good fit
  • A brief description of the the position that you are hiring for
  • Any other information you think is useful.

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Jackie Guan

Product manager, side project builder, and book worm