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Brand & Web Designer

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Founded in 2015, Headway was born out of a passion to bring entrepreneurial ideas to market and keep them there.

We help entrepreneurs build businesses - not just features.

We work holistically with our client partners as true product teams. We bring an ownership mentality to design, validation, and building great digital products. Our clients trust us because we focus on addressing risk head-on, learning quickly, and creating awesome products that customers love.

Our product strategists, designers and developers create incredible products that bring successful long-term partnerships and trusted referrals.

This approach, coupling an experimental-mindset 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!

Position Description

At Headway, as a Brand & Web Designer

You’ll be working within a multidisciplinary team of marketers, designers, and developers to evolve the Headway brand through various design and web projects.

A day in the life

During a typical work week, our crew members enjoy a balanced assignment of 35 hours on internal projects with the ability to invest the other 5 hours in 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 that encourages team bonding and goal setting, and a more focused week-long design and development sprint at our primary office in Wisconsin.

What does success look like?

During your first 2-4 weeks at Headway, you’ll receive extensive on-the-job training. This training covers the fundamentals of our core technologies, the way we delegate tasks within a marketing team, our process and workflow, strategies, and much more. You'll have dedicated pairing time scheduled with various colleagues to cover different skills. After this training period, you'll be successfully contributing to new initiatives in the context of the team. Welcome aboard!

Each week, you’ll meet with your team lead to ensure that you have the time and attention you need to be successful.

  • Project status / team issues / weekly retro

  • Individual quarterly goal progress

  • Individual responses to our weekly team health questionnaire

Quarterly & 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.

Why should you apply?

  • Help lead the evolution of the Headway brand
  • Work on various brand projects from our site to unique personalized goods
  • Strong leadership and top-notch colleagues to help you realize your full potential
  • Career growth and leadership opportunities

Work, Play, & Everything in between

Friday Team Lunches

Every week we meet as a team to share personal and professional wins while we break bread.

Onboarding Package

A $6,000+ hardware package; MacBook Pro, peripherals, and more!

Continuous Learning

35 hrs/week for client work and 5 hrs/week for investment time. We also host workshops and meetups.

Horizontally Structured

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

Flex Time

Work where you work best. We're remote-first. Need to take a break during the day? No problem.

Healthcare, Dental, & Vision

We cover 100% and offer PPO or HSA matching plans, and cover 100% of your dental insurance. We also offer vision coverage for a split cost.

Life & Disability Insurance

All full-time employees receive disability (Short and Long Term) and life insurance. (Term Life and AD&D) We also extend the opportunity for each employee to purchase additional term life and AD&D for yourself, spouse, and children.

Parental Leave

2 Weeks PTO, ample UTO thereafter.

Holiday Refresh

Headway HQ has a paid rest period between Christmas and the New Year.

Bi-Annual Retreats

Growing together and having fun. Hiking, snowboarding, hacking, team building, relaxing.


4 weeks of paid time off every year (vacation, sick-time, and holiday refresh).

Swag & Gatherings

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


We match 100% of the first 3%, and 50% of the next 2%. If you contribute 5%, we contribute 4%.

Quarterly Profit Sharing

As Headway continues to grow, so does your earning potential. Everyone at Headway is bought into our ongoing success.

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 Marketing & Brand Manager and 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.



  • The continued evolution of the Headway Brand and guidelines
  • Design new layouts and pages for websites in Figma
  • Working in Webflow: Building new pages, troubleshooting, maintenance
  • Creating concepts and graphics for events, websites, ebooks, ads, social, podcasts, YouTube, and more
  • Print design for apparel and gifts for team and clients
  • Storyboarding for motion design and videos


  • You have 5+ years of design experience
  • You have experience working in Figma
  • You have experience working in Webflow
  • You have experience creating brands
  • 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

Bonus Requirements


  • You live by our Guiding Manifesto and embody the core values of Headway
  • You enjoy working within multidisciplinary teams with marketers, designers, developers, and product strategists
  • 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, organized, 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 an excellent communicator (verbally and written)
  • 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

Make A Difference. Make Waves.

If this sounds like you, we’d love to have you apply! We’re a remote-first company so this position is open to anyone legally able to work in the US. All applicants are manually reviewed by our team.