Lessons Learned from my Job Search

Update (January 11th, 2016): I’m proud to say that this article was featured on the wonderful Zealify blog. Check them out for great job search tips, career advice, startup jobs, and more!


Nearly two months after leaving my job in Canada, I’ve officially accepted a job offer. I’m delighted to have signed on with Wall Street Systems to work on their IT2 treasury management software with, judging by my first few visits, an extremely talented, agile, and welcoming development team.

I had a great time at my interview and they seemed to like me despite my incessant asking of questions. Anyway, here’s what I learned in my job search.

The Numbers

  • 23 Jobs Applied to (Effort ranging from tailoring cheeky but professional cover letters- see below- to simply submitting my CV)
  • 8 Companies Responded (ranging from just a coding test to several stages of in-person interviews)
  • 1 Promising Application Withdrawn (I withdrew after a great final interview before they could make an offer)
  • 1 Job Offer (Accepted!)

Lesson One: Don’t Get Discouraged

I went through varying ups and downs that included several bouts of impostor syndrome– There were times that I started to doubt that I could bring value to any company. Fifteen different companies that I applied to didn’t even respond. On the flip side, though, over 33% of the jobs that I applied to DID respond, which seems to be much better than average (20%? 2%?). This type of thinking tended to help me during the downs.

Bottom line: Keep your head up and focus on the positives! Good things will come.

Lesson Two: A Little “Hustle” Goes a Long Way

A little bit of creativity can pay off hugely. Inspired by Zealify’s Career Hustlers Series, I decided to craft a personalized, tailored SwiftKey cover letter, complete with the SwiftKey-themed signature (see tweet below) and online stalking of the company’s HR team to learn about them personally.

I also got a great response from my “cheeky” cover letter for LShift that took the form of their “People” page.

About Page- Me Only-revised

Despite probably being a little under-qualified for the jobs that I applied for using those creative cover letters, I managed to land interviews with both companies. Neither ended up in a job offer, but both led to some great connections in the London tech scene.

Lesson Three: Work with Recruiters

There are lots of opportunities out there, so why not let recruiters help you find them? Recruiters sometimes get a bad rap, but remember that their job is to get you a job, so don’t be afraid of them!

Obviously, take what they say with a grain of salt and keep in mind that their main goal is to get you a job as quick as possible, not necessarily to get you your dream job, but they really can help. I particularly enjoyed working with Chris Curtis at FunctionalWorks and Kelly McCarthy at Huxley. Both put effort into getting to know me in order to help me find a great job.

Lesson Four: Trello is Awesome for Tracking Opportunities

My approach to the job search really evolved over time, but I couldn’t have done it without my beloved Trello board. Inspired by this post, I custom-made a board for my needs.

Keys to my approach were:

  • Dump all job-related information in one place. Someone mentions a job site I should check out? I quickly put it in Trello even if I don’t have time to check it out right now.
  • Send-to-Trello bookmarklet. Super handy for quickly adding jobs to my “To Apply” list

See below for a screenshot of the “jobs funnel”. The different colors on each card are because I used Trello’s tags to keep track of which of my criteria each job satisfied (for example, “Some, but not all C++”, “Intermediate Seniority”, and “Strong Development and UX Practices”).

Trello Job Board Job Funnel

Lesson Five: Trello is Awesome for Continuous Improvement

As always, incremental improvement can lead to huge gains. To take advantage of this, I tried to split my job-related tasks into bite-sized chunks like “Improve About Me Page on Website” and “Create a Slick Email Signature”. That way, when I had a free couple hours, I could pick one of my tasks and get it done. See below for the task-related section of my Trello board. Also shown is a list of job boards to keep an eye on, as well as the aforementioned job criteria.

Trello Job Board Tasks, Boards, and Criteria


The job search was a lot of work but it was worth it! I’m very excited to be working at Wall Street Systems and I expect to add a lot of value but also learn a lot there.

As an added bonus, their offices are in one of London’s most iconic buildings, 30 St Mary Axe (aka The Gherkin). In fact, before my interview, I just couldn’t resist sneaking a photo before heading in!

Picture I took of myself before my interview at The Gherkin

#PreInterviewSelfie #WorkinAtTheGherkin #SuitAndTieAndBackpack

Wish me luck!


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