Work at Headway

Apprentice Developer

Crew Description

If you recently graduated from college, a dev bootcamp, or are just diving into programming as a new career and are looking for your first job as a professional programmer, Headway wants to talk to you about joining our team as a junior web application developer! We have a history of bringing up driven, talented, green developers (regardless of age!) and would love to help you on the path to becoming a more proficient coder. We understand that “Senior Developers” don’t grow on trees, and we pledge to help you build and grow your skillset each week with cross-functional pair programming, lunch and learns, and the ability to join a diverse and motivated community of coders and makers through one of our many affiliations with community groups like Digital Fertilizer.

We're a small team, so we all wear many hats, but we're consultants first, so you'll need to be comfortable communicating complex ideas to clients in an easily digestible way. Estimating your work to help give ballpark costs to clients before starting an agile sprint cycle is also an important skill. Don’t worry though, each Apprentice Developer is paired with a mentor that will help walk them through how Headway operates. There is no shortage of things to work on or ways to grow your career!

Help us make a difference, make waves, and make headway!

What You'll Know

  • 3mo+ experience (doesn’t have to be professional / paid) with web application development (Ruby on Rails, along with other common libraries such as RSpec and Sidekiq preferred).
  • Basic understanding of object-oriented programming (even if you can’t always implement it correctly).
  • Basic understanding of JavaScript (ES6 is a bonus!).
  • Familiarity with server-side templating languages like HAML / SLIM / ERB.
  • Familiarity with server-side CSS preprocessors like as SASS / SCSS.
  • Familiarity with the concepts of MVC, ORM, TDD, and a desire to explore more about them!
  • The drive to write clean, readable code that communicates intent and is self-documenting.
  • Able to understand database schemas that represent and support business processes.
  • The desire to write automated tests to back up an exploratory code spike while working on TDD skills.
  • Familiarity with version control using Git (GUIs are fine to start).
  • Desire to pair program with other members of the team (sometimes cross-functionally).
  • Open to standardizing your toolset. We all use Vim + Tmux. Some of our clients even require it!


Work, Play, and everything in between.


We cover 100% and offer PPO or HSA matching plans.


We cover 100% of your dental insurance.

Continuous Learning

32 hrs/week for client work and 8 hrs/week for investment time.


15 days of vacation and sick-time off every year.


Work where you work best. We're remote-first.

Holiday Refresh

Headway HQ is closed between Christmas and New Years.

Horizontally Structured

We all grow together. Have a clear path for professional development.

Bi-Annual Retreats

Hiking, Snowboarding, Surfing, Relaxing.

Onboarding Package

A $5,000 on-boarding hardware package; MacBook Pro, Sitting/Standing Desk, and more!

Maternity & Paternity Leave

2 Weeks PTO for Fathers, 4 Weeks PTO for Mothers, Unlimited UTO thereafter.

Free Lunch & Learn Fridays

Every Friday a Team Member Presents on a topic they've learned about recently.

Swag & Gatherings

Get all the free gear you need! We also host gatherings, meetups & workshops.


Make a Difference, Make Waves & Make Headway

If this sounds like you, we’d love to have you apply! The position is full-time, includes 100% health & dental coverage, and comes with a $5,000 on-boarding hardware package! This position is primarily open to developers local to the Green Bay, WI area or people willing to relocate. We want to have you immersed in our culture and look forward to mashing some keys together as we sit (or stand!) at our modular workstations solving fun problems for awesome clients. However, exceptions can be made for outstanding candidates.

All positions at Headway are open to anyone who can legally work in the US. Headway does not discriminate on the basis of gender, race, age, ethnicity, or disability. We’re actively trying to build a culture of positivity, learning, and growth. Women and minorities are encouraged to apply!

Apply To Position


Inquiry Sent!

Thanks so much for your interest in working with us, and for your time to fill out the form. We're passionate about what we do and would love the opportunity to create a successful solution for you.

Expect to hear back from us within the next 3 business days.

Work With Us

We can take any type of project, but we only work with specific technologies that we are deep experts in and with clients who respect and embrace our systems. You should only partner with us on what we are great at.

We don’t take every project that comes our way, and we’re not always the best fit for every customer. That doesn’t mean we’re right, and everyone else is wrong, it just means that we’re different.

We diagnose before we prescribe. We show you a deliverable every two weeks. We’re looking for clients that value our knowledge, respect our process and want a partner, not another firm.

What type of project would you like to partner with us on?