Learn at Headway

Apprentice Designer

Crew Description

As an Apprentice Designer at Headway you'll work alongside our design lead and developers to learn the profession of modern digital product design.

We're looking for designers or front-end developers with about a year of experience and passionate about growing a career in technology and design.

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


The program runs for 12 weeks, in person at our office in De Pere, WI. It is a full-time program, running for 40 hours a week during normal business hours, from Monday to Friday.

During your first week you’ll be paired with a mentor to help guide you. For the first 6 weeks apprentices participate in lectures and an intense set of challenges meant to develop new skills. You’ll spend the final 8 weeks working directly on client projects with our team to cultivate valuable real-world experience. During this time we also teach interviewing and negotiation skills, help you with your portfolio, and make introductions to companies looking for UX talent (including Headway!).


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 open to designers local to the Green Bay, WI area. We want to have you immersed in our culture and look forward to mashing some keys as we sit (or stand) at our modular workstations together solving fun problems for awesome clients.

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!

Please send your resume, cover letter, portfolio, GitHub, dribbble and anything else that represents you to careers@headway.io!


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?