Remote Ruby Rails Developer Contract Jobs in Wisconsin

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 innovatorsbuild a business - not just an app. Our approach to validating ideas and building sustainable business models has been a catalyst for our growth.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 ourcase studies and see how our clients talk about our approach.

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 10 years, but we're just getting started. We need your help to take us to the next level!

Position Description

As a Senior 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.

This is a remote role embedded with an existing enterprise client as part of an integrated Headway + client delivery team. This engagement is expected to be medium to long-term, with the potential to stay on this client for a year or more.

Responsibilities
As a Senior Developer at Headway, you are responsible for 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 the product. In doing so, you help manage client expectations and project scope, ensuring we build the most valuable features first.

In addition, you:

1. Set and communicate technical direction for the mobile codebase (patterns, standards, and tradeoffs).
2. Own architecture and technical planning for features end-to-end (mobile + API integration), documenting decisions as needed.
3. Proactively manage technical debt through refactoring proposals and incremental improvements.
4. Mentor via pair programming, raising quality and consistency across the team.
5. Work effectively within enterprise constraints (security/compliance, access controls, release gates, device/testing requirements).
6. Collaborate with client stakeholders across product, QA, backend, and platform teams to drive alignment and delivery.
7. Make pragmatic technical decisions optimized for long-term maintainability, reliability, and incremental delivery.
8. Practicing "craft within context" and working with teammates to receive advice and guidance to grow your knowledge.
9. Assisting with development critiques through QA and pull request (PR) reviews.

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

Expectations

• 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 the 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 team weeks in Wisconsin, or at an awesome TBD destination.

What Does Success Look Like?
In the first 30 days:

• Ramp into the codebase, tooling, environments, and release process.
• Build relationships across the embedded Headway team and client stakeholders.
• Ship several small improvements in the mobile codebase.

By 60-90 days:

• Independently own a meaningful feature area and drive delivery with clear tradeoffs.
• Improve quality and reliability through tests, code review standards, and pragmatic refactors.
• Strengthen the feedback loop between product intent, implementation, QA, and release readiness.
  

Requirements

• 3+ years of paid, professional mobile development experience, including 1-2+ years with React Native.
• Experience with or willingness to learn native iOS and Android.
• Experience submitting and deploying apps to the App Store and Play Store.
• Experience with full-stack technologies like Ruby on Rails, Phoenix/Elixir, or Node, a big plus.
• Experience building using an atomic design system toolkit/set of well-organized and documented components.
• Excellent communication skills (verbal and written).
• The ability to present your work and stand firm for the right reasons.
  

AI-native development at Headway

• You actively use AI to plan, build, and test software - and can explain what you delegated, what you verified, and why.
• You can work effectively with AI pair-programming tools such as Claude Code, Codex, Tidewave, and similar agentic/code-assisted workflows.
• You can turn product intent into high-signal prompts/artifacts (user stories, acceptance criteria, edge cases, architecture notes) that an AI-assisted workflow can execute against - including reviewing existing docs/code before kicking off the work.
• You are comfortable planning/chatting in Claude Code (or equivalent) as a starting point for feature work; you may also use project management tooling if helpful.
• You treat AI outputs as drafts: you validate correctness (tests, types, runtime checks), security/privacy implications, accessibility, and performance.
• You can set up and maintain an AI-assisted feedback loop:
  • Scaffolding changes rapidly
  • Generating test cases (unit, integration, E2E) and translating them into real tests
  • Running CI locally
  • Debugging with logs/traces
  • Feeding errors/logs/plans back into AI to continue the loop
  • Iterating with small diffs and frequent commits
• You have good judgment about where AI helps vs. hurts (e.g., critical logic, security boundaries, unfamiliar codepaths) and can articulate tradeoffs.
• You can operate within real client constraints: IP/privacy boundaries, regulated data, and "bring your own model/tooling" limitations.
  

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).
• AI-native skills screen with a Development Lead (30 min).
• Live AI-assisted interview (60-90 min).
• Group interview with several members of the Headway team (45 min).
• Assessment exercise (1-2 hr).

AI-native skills screen
A practical conversation about how you use AI in real delivery work.

• Walk through a recent feature where you used tools like Claude Code/Codex/Tidewave (or equivalents): what you prompted, what you changed by hand, how you verified correctness.
• How you prevent "AI-assisted" regressions: tests, types, linters, CI, release discipline.
• How you keep client/workspace data safe while using AI tools.
  

Live AI-assisted interview
You'll drive on your own machine/setup/config while pairing with an agent/harness of your choice and an observing Headway dev, who is also available for collaboration.

• Use AI freely (Claude Code/Codex/Tidewave/etc.) to plan and execute.
• Build a small feature in a minimal repo with:
  • Clear acceptance criteria
  • At least one meaningful unit test
  • A manual QA script and an accessibility checklist for the feature
• We'll look for:
  • How you review docs/code before starting
  • How you turn plans + errors/logs into the next AI prompt
  • How you validate correctness and avoid regressions
  • How you communicate tradeoffs and scope in real time
    

Next Steps
If this sounds like you, we'd love to have you apply!