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Finding a Career You Love: Lessons Learned From My Job Hunt

I'm writing this article for someone who works in tech and is looking for a new job, but wants to be somewhat selective and build stuff they believe in. If that describes you, read on!


On June 3, I left my job at Punch Through, a hardware consulting firm in Minneapolis and San Francisco. My wife and I moved to Denver, CO. She's attending pharmacy school in the fall and I was looking for something new in my career.

Before I left Minneapolis, I started looking for a new job in Denver. Here's what I learned and what I would do differently.

Overview

  • What I Wanted: An overview of my target career and why I was so picky.
  • How I Searched: The boards and networks I used to find my dream job in Colorado.
  • How I Applied: How I got my foot in the door and how I kept the conversation going.
  • General Tips: Everything else that I think will help people searching for an awesome place to work.
  • How It Turned Out: The results. How many jobs I applied for, how many companies turned me down, and how many offers I received.

What I Wanted

I was in the market for

  1. a product manager role,
  2. or if that wasn't available, an engineering role with room to grow into management,
  3. with a team that cared about quality
  4. and worked on a product I believed in.

I loved my coworkers and the projects at Punch Through. I worked there for three years during and after college as a software developer. My primary work was on iOS, Android, and web software for LightBlue Bean, a Bluetooth Low Energy development board for makers and product designers.

Our team was small – about 16 people when I left – and we all had lots of ownership over the things we built. I enjoyed the responsibility of ownership and liked managing the Scrum backlog. I made it my short-term career goal to get into a position where I was formally responsible for a product's direction. Since my experience was in engineering, my friends and coworkers advised me to consider taking a dev role with the possibility of growth into management.

When I searched for companies to apply to, the specific product and industry were very important to me. If the best company in the world were hiring, but they weren't building a product I could be proud of, I would never apply for a job there. I avoided companies doing marketing and building social networks, and I refused to work in advertising tech.

How I Searched

I searched for leads through a few channels:

  1. Personal network and friends of friends
  2. Job sites: Glassdoor, Stack Overflow Careers, LinkedIn
  3. Community: Denver Devs, TechFriends Front Range, Built In Brews
  4. Recruiters: Dice

Personal Network

I reached out to my coworkers from Punch Through and friends living in Colorado and asked if anyone knew anyone building anything cool. Everyone was happy to pass along what they knew. I got very few leads through my personal network, but the ones I did get were all high quality – no fussing about, let's meet up for coffee and chat.

Job Sites

I searched job sites for the keywords Product Manager, Developer and Engineer.

Glassdoor has excellent data on job satisfaction which helped me get a quick idea of whether a team's culture was healthy. When most people are complaining about management not listening, not communicating, and hiring in managers from outside, that's a big set of red flags.

Stack Overflow Careers has less jobs listed, but most of them are high quality. People posting jobs on SO are encouraged to list the job's salary range, which is a breath of fresh air.

LinkedIn has everything but it's incredibly hard to find relevant postings or info. This is a last resort. What you should be using LinkedIn for is to find the name of a hiring manager at Acme Corp, figure out their email, and send them a nice cover letter directly. More on that later.

Community

All three of the communities I listed were excellent leads for awesome companies. The Denver Devs Slack channel has a weekly Gigs Day: employers post about open jobs and individuals post if they're looking for a job. It's a great way to skip the recruiting site and ask some quick questions to see if you're a good fit.

Built In Brews is a fantastic networking event. Show up at an awesome office, have some food and drinks, and chat with other awesome people. I got in touch with a couple of excellent recruiters who set me up with great companies. Their parent site, Built in Colorado, also has a job posting board with lots of great leads.

Recruiters

The easiest way to get recruiters to do the legwork for you is to put your resume on Dice and list your relevant skills. You'll get calls and emails for the next month with stuff that is – surprisingly – mostly relevant! The quality is mixed but there are a couple of diamonds in the rough. For example, many of the recruiters that reached out were filling Contract or Contract to Hire roles, even though I was seeking full-time exclusively. But the calls I got for full-time roles were mostly real jobs where my experience was relevant.

One recruiter was a complete asshole. They called me once to see if I was interested in the role and the industry. I was, so they sent over the job details. I liked them, so I scheduled a Skype call. Here's how that call went once we got past small talk:

Them: "How much did you make at your last job?"
Me: "Sorry, I prefer not to say."
Them: "I really need to know."
Me: "Sorry, I don't want to cap my next salary by stating that. But I can tell you what I'm targeting."
Them: "Let me worry about that. What did you make at your last job?"
Me: "...I really can't give you that number for several reasons."
Them: "I understand. Sorry this didn't work out. Have a nice day." Skype hangup

I don't think I could fix that recruiter's broken behavior. There are so many things wrong with what they said and did. Between the blatant disrespect, lack of professionalism, and the Skype equivalent of slamming the phone down, I'm amazed that Asshole Recruiter moves forward with anyone in the hiring process.

Pro tip – don't say Let me worry about [your salary], because I will worry about my salary. Thanks.

How I Applied

OK, I have a big pile of job listings. How do I turn those into interviews?

Here are the approaches I used, from most to least successful:

  1. Get a personal introduction from a friend of a friend and send them a nice cover letter
  2. Find the hiring manager's work email and send them a nice cover letter
  3. Apply for the job online with a nice cover letter

Notice anything in common?

The Cover Letter

This is the cover letter skeleton I used for 90% of my job applications. I think it struck a balance of giving them information about me, letting them know what I wanted, telling them why I'd be a great pick, and asking to move forward in the process.

Hello! My name is $NAME. [Why I'm looking for a job right now.] My last position was as a $ROLE at $COMPANY, a $TYPE_OF_COMPANY in $PLACE. I wanted to get in touch with you because I’m looking for a position building $TYPE_OF_PRODUCT, and I really like the sound of $COMPANY. I think your company is a great place to $PROFESSONAL_GOAL.

[Brief history of my time at my last company. Any of my relevant experience with impressive KPIs attached.]

I want to work with $COMPANY because $COMPANY_CULTURE. [Short blurb about stuff I saw on their site or read about the company that would make me happy to work there.]

I feel my experience in $RELEVANT_EXPERIENCE will fit right in at $COMPANY. [Sentence about how my personality fits with the company culture. Sentence about how my experience is relevant. Sentence about how I can start adding value as soon as I'm hired.]

I’d like to chat with you sometime. I want to learn more about $COMPANY's needs and let you find out if there’s a place I would fit in.

Thank you for your time!

$NAME
$WEBSITE
$PHONE_NUMBER

Please feel free to steal this template and use it yourself. This letter is brief, to the point, and professional. If your paragraphs start looking longish, consider shortening them. It's a cover letter, and the goal is to get the hiring manager on the phone so they can ask about what they really care about.

It's important that this letter has your voice in it. Think business casual, not T-shirt and shorts. Some excitement (!) and some talk about your personal reasons for looking for a new job is OK. Emoji is not.

Always ask for the job! It's important to ask for the job throughout the process. It's not aggressive – it's professional. Asking for the job makes it clear that you're interested and want to be put at the top of their list.

After an email, ask when they're available for a call. At the end of a phone call, ask what the next steps are. After an interview, ask when you should expect to hear back from them on a decision.

Great – you have a cover letter. How should you get it to the hiring manager?

Personal Introduction

If you can get someone to CC you into a conversation with the person responsible for hiring, you have just saved yourself weeks of waiting for them to check the inbound resumes. Ask your friends if they would be comfortable with introducing you to hiring at their company, and nudge them until they send the email.

Email the Hiring Manager

There are a couple of tricks to this one. You can often leverage LinkedIn to help you find the hiring manager. Once you know who they are, you can usually guess their email based on the email addresses of other people at the company. Here's a good set of tips.

Just Apply Online

When you apply online, assume your resume will go to the glorious digital circle file and never be seen again. I consider it a happy accident when someone actually responds to my online application. Don't forget to write a cover letter for online apps – it goes a long way.

General Tips

Here's stuff I wish I had known when I started my job hunt.

Plan For A Long Hunt

My job hunt took ten weeks total. When you start your search, plan to be looking for at least a few weeks.

A few weeks?!

Yes, a few weeks. The longer you hunt, the more you apply, and the later you wait, the better your odds of finding the job you really want. Unfortunately, that gets a bit stressful when you don't have steady income coming in.

I wish I had had a job lined up by the time I moved to Denver. If I were to do this all again, I'd start hunting a month earlier.

Set Clear Expectations

In my first few interviews, I told the interviewer I wanted a position in management even though I was applying for a dev role. I told them that I would be happy to grow into a new role. This spooked my interviewers – they were worried I would be dissatisfied with my job and leave if I didn't get a promotion to management quickly.

I honed my approach as I went through more interviews. Instead of saying "I want to move to a mangement role sometime," I asked about the company roles and culture. I asked if the company was big enough to hire product managers, and if they tended to hire from inside. I asked questions like "If I were to work here and I liked it a lot, is there room to grow?"

Those questions helped me understand what roles I could move into without making them think I wouldn't be happy with an engineering role.

Be So, So, So Organized

Use iCal. Use Google Calendar. Use Fantastical, my favorite Mac and iOS calendar app. It doesn't matter what tool you use – just use some tool. When you apply for five to ten jobs a day, you will need a calendar to tell you who you're talking to and when.

Show up early. 30 minutes early is acceptable. 15 minutes early is ideal. If you arrive on time, you are late. When you're trying to find parking in downtown Denver, you'll pass the lot you want twice. Then you won't be able to find the office. (Not that I know from experience.)

If you screw up, completely flub an interview time, and don't show up, you might be screwed. But you can usually salvage it if you are very apologetic and polite and extremely thankful that they gave you another shot.

Always Say Thank You

Any time you finish a phone call, a meeting over coffee, or an in-person interview, send that person a thank you note the next day. It doesn't have to be anything fancy. Just email them saying you appreciated their time and mention what you liked about the last interaction. For example:

I was happy to learn about the role and my day-to-day responsibilities.

I liked meeting Sam and getting a feel for the engineering culture at E Corp.

I enjoyed learning about the roles you have available and I'd like to learn more.

Sending the thank you note the next day keeps your interaction fresh in their mind. Don't forget to ask for the job!

Be Politely Pushy

You've gotten in touch with hiring. Now you're sitting and waiting for them to get back to you. What's the etiquette on bugging someone you hardly know after they don't email you for weeks?

My rule is: Wait three to five business days and ping them again. You need a job and being too polite will hurt your chances. If someone hasn't returned your email or scheduled a call with you, send them one of these:

Hey $NAME,

Just wanted to check in and make sure I'm still on your radar. I'd like to move forward at $COMPANY. Are you available for a call this week?

Thanks,
Matt

It's a polite reminder that you're still interested but do need a response soon. You can send a few of these in a row if you wait a few days and still don't hear back. If you send three of these and don't get anything back, assume they ghosted you and aren't interested.

Set A (Fake) Deadline

I started applying for jobs on May 2. I accepted a job on July 16. This was way longer than I thought I would spend job searching.

Once I got my first offer from a Boulder dev shop, I asked them for just over a week to consider the offer. Then I told all the other companies I was still interviewing with that I had an offer on the table. Once I told them I had a deadline, the managers hustled to get me through the process. One mid-sized company flew me to SF in the morning and back at night the day before my deadline, while another got me a last-minute on-site appointment to finish up the process with two engineers and a hiring manager.

The lesson? Most places can lift heaven and earth to move you through the process – but they aren't incentivized to unless you tell them they have to. The next time I seek a job, I'm setting a deadline to encourage companies to move it.

How It Turned Out

I applied to 26 companies. This doesn't include recruiter gigs that fell through or positions I wasn't seriously interested in. Here's how those turned out:

9 companies dropped out because I couldn't get in touch with them.

  • 4: No response. I applied online and no one got back to me.
  • 5: Ghosted. I started talking with a recruiter or hiring manager and they refused to respond after I pinged them several times.

13 companies didn't give me an offer for one reason or another.

  • 2: Situation mismatch. They were looking for something totally different. One manager wanted to hire someone like me but couldn't get a budget in time. One team found a lead developer in Pennsylvania and wanted me to relocate.
  • 3: I declined to continue the process. I didn't have time to complete their code test, or they got back to me too late in the process and I had to accept an offer.
  • 8: Job not offered. I wasn't a good fit for the position or they found someone they preferred.

4 companies got back to me with an offer. I turned down three offers and accepted one.

Conclusion

I feel OK about the job hunt. Four offers out of 23 serious applications sounds low, but at each step along the way I learned more about the companies and the roles I was applying to. It was occasionally disappointing to be turned away, but I'm glad I didn't end up working somewhere where I would be a poor fit for the role.

I'm happy where I ended up: a Project Management position at a connected device company. That's exactly what I was looking for when I started my job hunt, and I'm glad I found a growing company that was looking for someone like me.

I don't look forward to searching for a job, but I'm confident I will be able to navigate the interviews and hiring process much more easily next time.