How to Level Up Your Engineering Career

Practical Lessons from Headlight’s Panel Discussion

Jason Shen
Headlight
6 min readApr 26, 2018

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From left to right: Sam Lau, Vesha Parker, Frantz Joseph, Jason Shen

Note: if you’re hiring full-stack developers in the greater New York City area, we recently completed the NYC Engineering Tournament and have a number of proven software engineers we’d love to connect you with.

While there is a lot of content out there about learning to use new languages or frameworks, adopting coding practices, or learning from failed or successful projects, there’s not much out there that really talks directly about career advice for engineers. Things like how to pick the right place to work, what the skills are necessary to succeed, and how to get hired or promoted.

So last week, Headlight hosted an panel discussion and mixer at Brooklyn Commons called How To Level Up Your Engineering Career.

Our panelists for the evening were:

About 30 developers were in attendance as our panelists talked about how to work well within the engineering org, learn new skills, take on more interesting and challenging projects, and get paid what you’re worth.

While the discussion was not recorded, here are a few highlights from the evening:

Frantz Joseph and Jason Shen

Have regular conversations about your career with your manager

Talking about your career isn’t always comfortable, but it’s important. Your manager needs to know what your goals are so they can support them and you should never be surprised when you are (or are not) promoted.

One thing that Frantz Joseph tells his reports is that career conversations are always on the table. And to ensure they happen, every 8th one-on-one conversation will focus on career progression to make sure it never gets missed.

Vesha Parker and Frantz Joseph

Know yourself and the environments you thrive in

To have a successful career, you need to choose the companies you apply to work at with care. Different companies have different cultures and knowing what kind of environment you will succeed in is important.

Vesha Parker explained that she graduated out of a very competitive computer science program and many of her peers were going to work for big companies like Facebook and Microsoft, which were also known to have fast-paced and aggressive cultures. After interning at Etsy, she realized how deeply she appreciated being at a place where people were respectful and considerate, and has continued to stay at Etsy ever since.

Veronica Ray speaking to a panel attendee

Really understand what it takes to be promoted

Those career conversations with your manager are important because they most likely understand what it will take to get you a promotion. Ideally your company has published a consistent system for leveling and promotions or a competency matrix to align against, but even if it does, there’s always more nuance than meets the eye.

Veronica Ray went through the promotion process in 2017 to become a senior iOS engineer at LinkedIn, which required helping her manager build a huge packet of evidence that showed she was performing at the senior level on every aspect of the role. She sometimes had to go beyond her comfort zone and work on new kinds of projects and activities in order to demonstrate that she met the requirements for her new level.

She also spoke to people who had recently been promoted for advice and to understand what to expect in terms of increase in salary and stock options. This enormous amount of preparation and research allowed her to make a strong impression on the review panel and successfully negotiate a generous but fair bump in compensation.

From right to left: Sam Lau, Vesha Parker, Frantz Joseph

Invest the necessary time to prepare for interviewing

While the current state of engineering interviews has continued to evolve (there are probably fewer puzzles, gotchas, and brainteaser than there were a decade ago) many engineers can still be frustrated by hoops they have to jump through in the interview process. Companies like interviewing.io, Triplebyte, and of course Headlight are working to change that, but of course the industry doesn’t shift overnight.

Sam Lau, who I had the opportunity to work with in his first full-time engineering role, and has at worked a Series A+B funded startups and publicly traded companies, says he treats interviewing like a job. When he looks for a job, he makes sure to devote at least one full month just boning up on algorithms and whiteboarding experiences, using resources like How to Crack the Interviewing Code and CareerCup to prepare. While it’s a pain in the butt, it’s just part of the process, at least for now.

Izzy Oji (far left) and panel attendees

Don’t sweat side projects (unless they’re strictly for fun)

I’m personally a big fan of side projects, but I recognize that it’s not everyone’s cup of tea. When the panel discussion got on this topic, most people felt as a hobby, side projects are great. But as a career investment, it might only be useful for someone at the very early stages of their engineering career or if they don’t have a lot of other work they can share publicly.

As Izzy Oji put it, she loves life. She is 100% focused and diligent at work but when 6pm rolls around, she is closing up her laptop and doing aerial yoga, learning Arabic and exploring NYC’s many museums. As a member of the interview panel for a mobile engineering manager opening at Kickstarter, she does not hold the lack of a side project against any candidate.

Jason Shen and Wayne Gerard

Take a deep breath before sending an email or chat message when angry

Beyond just being a strong technical contributor, what else do you need to make an impact and get promoted? One topic that came up often in the evening was the importance of “soft skills”. The importance of being a trusted and respected member of the team cannot be overstated.

Headlight co-founder Wayne Gerard has a rule that even under stressful situations, like when the site is breaking or a major bug has blown up, he makes sure to communicate respectfully. If he feels himself wanting to write an angry and possibly hurtful message to someone he blames for the problem, he stops himself, waits a few minutes, and revisits the message. You can always send a message later, but you can’t take back a message you’ve already sent.

We were thrilled to have an evening full of lively conversation and were excited to share some of the lessons from the event. We expect this first panel is just the beginning of the kind of public events Headlight will host, so stay tuned.

Note: if you’re hiring full-stack developers in the greater New York City area, we recently completed the NYC Engineering Tournament and have a number of proven software engineers we’d love to connect you with.

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Jason Shen
Headlight

Rediscover your spark and come back stronger | Executive coach • PM for public groups on FB • the resilience guy • 3x startup founder • Stanford gymnast 🏆