We are not actively seeking to hire right now for this future opportunity, we are always looking for talented individuals who are interested in working alongside our team. If you are interested in this role, please submit an application and we'll reach out as soon as this opportunity opens.

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 and in 2021 at #2765. 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, Even Keeled, a podcast about the craft of creating software and effective development teams, and Exploring Product, a show where we go behind the scenes on what it really takes to bring a new product to market.

We're 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. Twice a year, 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 and a more focused week-long design and development sprint at our primary office in Wisconsin. Check out our 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 training including a customized trail of technical assessments and assignments. This training covers the fundamentals of our core technologies, our 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.

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 2022. 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
  • 4 weeks of paid parental leave.
  • 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 3-5 days (depending on scheduling):

  • Work history and aspirations chat with our People and Team Strategist.
  • Skills and performance discussion with our Head of Design and a Design Lead.
    • Portfolio Review
    • Design Collaboration Exercise
  • Take-home skills assessment.
  • EQi and Kolbe assessment exercise.
  • Group interview with several members of the Headway team.

Position Description

As a Senior Designer, you’ll be working within a small multidisciplinary team of designers, developers, and product strategists. You'll be working on applications and web projects, although sometimes you'll be guiding your own ship on a smaller adventure.

You'll be working closely with our team and clients to challenge assumptions, create small experiments, in-depth prototypes, detailed specifications, and style guides.

With a high priority on business and user needs, you'll help make decisions that stand up for users to solve their problems and create true value in their lives.


You are responsible for executing within our design process with a focus on client and user needs including:

  1. Practicing "craft within context" and providing designers and apprentices guidance
  2. Driving all design from the outside-in with user story mapping and MoSCoW prioritization
  3. Assisting with design critiques and QA
  4. Participating in pairing sessions to help crewmates learn and grow
  5. Performing QA of both internal design quality and end-user UI/UX
  6. Conducting user interviews, creating small experiments, in-depth prototypes, detailed specifications, design systems, and validation
  7. Setting project design direction and following through with successful execution and delivery
  8. Interfacing with clients during sprint planning sessions and retros to ensure projects are on track
  9. Leading product/project discovery sessions and workshops with necessary internal and external stakeholders


  • You have 5+ years of experience
  • You have experience shipping applications for Web, iOS, and Android
  • You have experience working with businesses at different levels of maturity
  • You have professional knowledge of user-centered design, usability principles, and techniques
  • You have the ability to present your work and stand firm for the right reasons
  • You have experience working within Agile/SCRUM processes
  • You have the ability to think big whilst being detail-oriented and delivery focused
  • You enjoy working within multidisciplinary teams with UX designers, visual designers, and developers
  • You enjoy communicating and working with developers to solve technical challenges
  • You enjoy visualizing and prototyping concepts to varying levels of fidelity to demonstrate and test ideas
  • You are passionate with a hunger to design and make things people use every day
  • You are organized and self-motivated
  • You are an excellent communicator (verbally and written), capable of inspiring colleagues and clients
  • You are outgoing, personable, sociable, and easy-going
  • You are open to criticism from your team to benefit project development
  • You are always eager to learn and to share knowledge
  • You are able to deal with pressure and can work in a fast-paced environment
  • ++ You have the ability to develop your own designs with CSS/HTML & Javascript
  • ++ You have experience with interaction prototyping tools like Framer, Invision Studio, Principle
  • ++ You have experience designing branding and identity
  • ++ You have experience running or participating in design sprints


  • 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 designers local to the Green Bay, WI area, and anyone residing in and legally able to work in the US.