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 an 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, developers, and product strategists, we achieve results that bring successful long-term partnerships and trusted referrals. We help entrepreneurs and corporate innovators build a business ― not just an app. Our approach to validating ideas and building sustainable business models has been a catalyst for our growth. In 2020 we were honored to be named to the Inc. 5000 at #918. 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.

View our case studies and see how our clients talk about our approach. If you're a podcast fan, check out Seaworthy, where we explore ways to help companies grow and scale their business and ideas, and Even Keeled, a podcast about the craft of creating software and effective development teams. We are also actively engaged with our community through various live streams and videos to help startups and product teams reach their goals. We're excited about what we've achieved in the last six 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 have an opportunity to meet with lots of crew members across the company and start to understand our unique approach to product development. This includes several "Headway 101" sessions that cover everything from our project management style, to our design aesthetic and business analysis approach, to development tools and techniques. If you're new to one of our tech stacks, we'll also create a customized trail of exercises to help get you up to speed. This training covers the 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.

After this initial 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 touchpoint 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, product, and operations, Headway is poised for an amazing 2021. Our business is guided by EOS and we have strong processes, documentation, and people to support your growth and development. 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 the following:
    • Healthcare and Fitness
    • Financial Technology
    • Logistics and Supply Chain
    • Social and Communication
  • 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

    • 3 weeks of PTO & Sick Time available immediately.
    • 1 week of additional time off during the winter holiday season.
    • 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 onboarding budget including $2,500 to spend however you like.
    • $2,500 annual education and conference budget.
    • Quarterly profit-sharing bonus plan.

      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 1-3 weeks (depending on scheduling):

      • Work history and aspirations chat with our People and Team Strategist (30 min).
      • Skills and performance discussion with a Development Lead (30 min).
      • Take-home skills assessment with the potential for follow-up/discussion/remote pairing at this stage (3-4 hours).
      • Group interview with several members of the Headway team (45 min).
      • EQi and Kolbe assessment exercise (30 min).

        Position Description

        As a Developer at Headway, you are client and user-focused while executing on the details of each project. You diligently develop features and functionality, guided by Headway's process to ensure each release is successful. This role requires constant learning and a growth mindset.

        When communicating with clients during sprint planning, retros, and release demos, you help monitor features 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 client expectations and project scope, ensuring we build the most valuable features first.


        As a Senior Developer / Tech Lead at Headway, you are responsible for executing within the Headway development process with a focus on client and user needs including:

        1. Setting the project development direction consistent with Headway technology and standards.
        2. Creating architecture diagrams, flowcharts, and ER diagrams to increase the team's understanding of project scope and support the overall development process.
        3. Helping to enforce development process and consistency across the team.
        4. Performing development critiques and QA on pull requests ensuring Headway development process is followed.
        5. Suggesting refactoring that will help curb technical debt and grow knowledge across the team.
        6. Conducting pairing sessions to help developers learn and grow while also evaluating their craft, including: efficiency, adherence to process, and overall professionalism.
        7. Performing QA of both internal code quality, interfaces, architecture, tests, and external end-user UI/UX.
        8. Interfacing with clients during sprint planning sessions and retros to ensure projects are on track and on budget.
        9. Driving all meetings and development activities from the outside-in with user story mapping and MoSCoW prioritization.
        10. Helping assess potential hires for technical ability and team fit for future positions at Headway.

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


          • 4+ years of paid, professional Ruby on Rails experience (required), with Elixir/Phoenix and React experience a plus.
          • Experience leading project 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 twice-annual 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! We're a remote-first company so this position is open to developers local to the Green Bay, WI area, and anyone living in and able to work in the US.