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Full-Stack (Rails) Developer


Posted: May 14, 2019

About Headway

Founded in 2015, Headway was born out of a passion to bring entrepreneurial ideas to market and keep them there. We work holistically with our client partners as a true extension of their product team, not just as the technical execution arm of their business. If we see something broken, whether that's a workflow, a marketing or messaging strategy, or a needless feature, we speak up, and our clients trust us to help them fix it.

Because we're more than just designers and developers, we achieve results that bring successful long-term partnerships and trusted referrals. We help entrepreneurs build a business not just an app. This approach, coupled with realistic and incremental software releases, results in a friendly, fun, and collaborative atmosphere where our colleagues and clients both have room to learn and grow.

See how our clients talk about our approach and check out some of the recognition we've received so far. Discover how we show our clients appreciation with unique holiday gifts each year. Or, if you're a podcast fan, check out Seaworthy, where we explore ways to help companies grow and scale their business and ideas. We're excited about what we've achieved in the last few years, but we're just getting started. We need your help to take us to the next level!

A Day In The Life

During a typical work week, our crew members enjoy a balanced assignment of 35 hours on client projects with the ability to invest the other 5 hours on a combination of individual goals and team meetings. Each quarter, we take a full week away from client work to focus on team goals and internal project initiatives. These weeks alternate between a retreat style destination that encourages team bonding and goal setting, and a more focused week-long design and development sprint at our primary office in Wisconsin. Check out some of our team week recaps and years in review to get a feel for how much fun it is to work at Headway!

What Does Success Look Like?

During your first 2-4 weeks at Headway, you'll receive extensive on the job training including a customized trail of technical assessments and assignments. This training covers fundamentals of our core technologies, the way we delegate tasks within a development team, our git process and workflow, testing strategies, tips for successful client interactions, and much more.

You'll have dedicated pairing time scheduled with various colleagues to cover different skills, and we'll even participate in several mock client meetings so your first standup or sprint planning meeting doesn't carry with it the weight of your first client interaction. After this training period, you'll be successfully contributing to new feature work on a client project in the context of a team. You'll also be participating in daily standups, sprint planning meetings, and retrospectives. Welcome aboard!

Ongoing Support

Each week, you'll meet with your team lead to ensure that you have the time and attention you need to be successful. Your needs and questions will always come first in this meeting, but other topics discussed include:

  • Individual quarterly goal progress
  • Project status / team issues / weekly retro
  • Individual responses to our weekly team health questionnaire

Quarterly and Annual Reviews

In addition to weekly touch point meetings, more formal quarterly reviews are scheduled to discuss successes and areas for growth identified over the last 3 months. We have annual performance assessments and salary reviews, though we reserve the right to provide a merit based pay raise at any time. Most crew members achieve between a 2% and 5% raise each year within their same role, but bigger jumps are possible when roles or responsibilities increase. We're here to grow with you sustainably over the long term.

Experience and Results At Every Level

With an experienced leadership team encompassing design, development, sales, marketing, and operations, Headway is poised for an amazing 2019. Our business is guided by EOS and we have strong processes, documentation, and people to support your growth and development at Headway. As they say, “Train people well enough so they can leave, treat them well enough so they don't want to.” For more on that, check out our benefits!

Why Should You Apply?

  • Work on exciting projects in the latest tech across a variety of industries including: Healthcare, FinTech, Education, Personal Growth & Training, Lifestyle & Social
  • Collaborate with colleagues and clients directly to ship features that users love
  • Work with appreciative clients who seek out and value your input and feedback
  • Strong leadership and top-notch colleagues to help you realize your full potential
  • Career growth and leadership opportunities

Key Benefits

  • 19 total days of PTO & Sick Time available immediately
  • 100% of health care and dental premiums paid for you and all your dependents
  • Up to a 4% matching 401k contribution based on your dollar contribution
  • $6,000 hardware on-boarding budget including $2,000 to spend however you like
  • $2,500 annual education and conference budget

The Hiring Process

If after we review your application and we choose to move forward, the following interviews will typically take place over the course of 3-5 days (depending on scheduling):

  • Work history and aspirations chat with our People and Team Strategist
  • Skills and performance discussion with a Development Lead or the Head of Development
  • Take-home skills assessment with the potential for follow up / discussion at this stage
  • Discussion with a member of the design or development team

Position Description

As a Developer at Headway, you are client and user-focused while executing on the details of each project and keeping it on course. This requires fostering individual learning and growth of less senior folks on the team as well as narrowing in on project specific details and client needs. You help your team reach and execute on a shared vision to ensure each release lands successfully on time and budget.

When communicating with clients during sprint planning, retros, and release demos, you help monitor features and architecture as project requirements change, and direct emergent requirement discussions back to the core focus of a minimum viable product (MVP). In doing so, you help manage a client's expectations and project scope to the budget they have allowed while still ensuring we're building the most valuable features first.


As a Developer at Headway you focus on the following:

  1. Creating architecture diagrams, flowcharts, and entity relationship diagrams to increase the team's understanding of the scope and support the overall development process.
    1. Setting the project development direction consistent with Headway technology and standards
  2. Helping to enforce development process and consistency of each of your project's crewmates through:
    1. Development critiques and QA by:
      1. Performing pull-request (PR) reviews:
        1. Ensuring CI passes for each PR
        2. Testing code within your development environment when appropriate
        3. Suggesting refactoring that will help curb technical debt and grow knowledge across the team
        4. Ensuring Headway development process is followed by all (FBA) on each git commit and PR
      2. Conducting pairing sessions to help developers learn and grow while also evaluating their craft, including: efficiency, adherence to process, and overall professionalism.
      3. Performing QA of both internal code quality, interfaces, architecture, tests, and external end-user UI/UX
      4. Creating release notes for each release, internal or external, and thoroughly testing the current version of the code, documenting known issues with annotated screenshots.
  3. Interfacing with clients during sprint planning sessions and retros to ensure projects are on track and on budget
    1. Driving all meetings and development activities from the outside-in with user story mapping and MoSCoW prioritization
    2. Taking notes collaboratively alongside the rest of the team
  4. Executing on development process consistent with a client and user focus
    1. Practicing "craft within context"
  5. Helping assess candidates for technical ability and team fit for future positions at Headway

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


  • 2+ years Ruby on Rails and React experience (required), with Phoenix (Elixir) or Node experience a plus.
  • Experience working with teams of both internal and external stakeholders.
  • Excellent communication skills (verbal and written).
  • The ability to present your work and stand firm for the right reasons.
  • Experience working with businesses at various phases of creation and growth a plus.


  • You live by our Guiding Manifesto and embody the core values of Headway.
  • You are open to criticism from your team and are always eager to learn and to share knowledge.
  • You have the ability to think big while being detail oriented and delivery focused.
  • You are self-motivated and able to deal with pressure and work well in a fast paced environment.
  • You have an outgoing, personable, and sociable attitude.
  • You have initiative to solve challenges, meet goals, and set new directions based on data.
  • You are capable of inspiring colleagues and clients.
  • You have a passion to create useful and valuable solutions.
  • You prioritize and attend our quarterly team weeks on-site at our primary office in Wisconsin, or at an awesome TBD destination.

Next Steps

If this sounds like you, we’d love to have you apply! This position is open to developers local to the Green Bay, WI area. If you don’t feel that you meet or exceed the requirements above, we encourage you to apply to our Apprentice Developer position! We have a track record of bringing up driven developers and would love to coach you through the next phase of your career.


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