TECH CAREERS
This guide is broken up into the following sections
Intro and Questions to Ask Yourself
Getting a job in tech is hard. I had a very good resume of technical work in the military, got great advice, had advocates within companies, and it was still very hard. You can still have good outcomes (e.g,. Become a product manager, make money, land at a cool company) but recognize that it’s difficult, requires luck, and may be a multi-hop journey rather than a linear path.
You likely will not land your dream job immediately. You will make compromises (pay, location, brand, work-life balance). Think about what matters most to you and what is the highest priority vs what is negotiable. I’ve met very senior engineers who didn’t get their ideal 1st (or 2nd) job.
Be kind to yourself. Job searching is stressful and overwhelming at times. It’s extra stressful when you’ve never done it before and when your end of active duty is looming. Don’t get stuck in decision paralysis—make a plan, aim at a target role, start working towards it. It will be stressful but you’ll learn a lot and grow a lot. Take care of yourself. Be kind to yourself.
Questions you should ask yourself early on
What problem in the world do I want to work on solving? (this defines industry)
What is the best way to solve that? (e.g., a big corp, existing startup other?)
What are my goals in 5 years if everything goes perfectly?
What are my career goals?
Am I competitive for the roles I want right now? If not, can I upskill before I transition? If not, can I get into a position that will make me more competitive for that eventual dream job?
What are my financial goals?
Note that taking a lower compensation role with the right fit/team/company may have a higher return on investment in the long term
What am I seeking?
Fast paced? Structure? Learning (what kind)? Autonomy or part of a team that collaborates? Growth opportunities? Financial security? Internally- or externally-facing projects?
What type of company do I want to work in?
Public vs private?
How do I feel about working with the government?
In government focused companies (e.g., Anduril)
In a government role within a heavily commercial company (e.g., AWS public sector)
Is doing government work a dealbreaker for me?
Do I put more emphasis on the work I do (e.g., tech area) or the company I work at?
Do I want to work in a specific vertical (e.g., health-tech)
Is location important to me? Is remote work important to me?
How long can I wait before needing a job?
How much vacation/time off/decompress time do I want before moving into a new job?
Strong recommendation: Take a month off between roles to recharge
Location Thoughts / Constraints
Where does location fit on your list of priorities?
What works for your family (if applicable)?
Don’t put your location on your resume if you’re willing to relocate for the job. A SF-based company may see “Augusta” on your resume and screen you out.
San Francisco / Silicon Valley and Seattle are the biggest tech hubs. New York and Austin are sizable. Some smaller ones exist too (e.g., Raleigh-Durham, Pittsburgh)
Larger tech hub = more stability in tech career (more jobs in the region), also higher cost of living (SF, NYC) and can lead to lifestyle creep
Companies like to hire to their headquarters, though they have satellite offices (e.g., Meta has an office in Washington DC).
Software engineering and engineering-adjacent roles (product, technical program management) are more commonly at large offices where you’ll be co-located with teammates working on the same products. This means that Meta may have a DC office but it may not have many engineering roles there.
Remote is not nearly as available as it was in 2021. Expect to be in the office 3+ days a week unless the recruiter / job posting says otherwise.
Washington DC has a lot of federal engineering roles
Preference for TS/SCI with full scope polygraph
Roles at Microsoft usually say “CTJ” in it for cleared jobs
Both Amazon and Microsoft offer bonuses for holding a clearance in cleared roles. If I recall correctly it’s ~$15k
Do you want to live somewhere new? Apply for roles there! You’ll rarely have this opportunity to geographically reset
Be transparent about your location preferences. Some companies may be flexible between major offices (e.g., SF vs NYC) but don’t waste everyone’s time if you know you aren’t willing to live in that location
Timing
Start preparing for transition early. > 6 months for sure, > 12 months if you can. There’s a lot to learn that you probably never covered in your military career
For SWEs, if you are not in a SWE role now and > 12 months out from transition, having a serious coding side project can be a really helpful talking point
For SWEs, if < 6 months out, grind leetcode until you know question patterns easily