Software Engineer

About the Company

A profitable, YC-backed workforce technology company is modernizing the way enterprise businesses manage their contract and contingent workforce. Their platform handles sourcing, employer-of-record employment, time and attendance, cost center allocation, and workforce management at scale — replacing a legacy industry built on manual processes and spreadsheets with real software.

The company has been operating for over a decade and recently reached consistent profitability after a self-imposed two-year hiring freeze. They are now in growth mode, rebuilding a lean engineering team that moves fast, ships thoughtfully, and is actively investing in AI tooling as a core part of how they work.

The engineering team is approximately 8 engineers. Code quality standards are high. On-call burden is very low.

The Role

This is a senior individual contributor role on the Feature Team. You will work inside a large, modular Ruby on Rails monolith and own product features from initial problem definition through deployment.

Work arrives as loosely defined business problems, not detailed specs. Senior engineers here bring context, shape solutions, clarify tradeoffs, and deliver changes that the next engineer can build on. You will work closely with product managers, review code with an eye toward long-term maintainability, write and maintain automated tests as a first-class responsibility, and use AI coding tools to increase your throughput without sacrificing accountability for what you ship.

This is not a ticket-execution role. You are expected to think like a product-minded builder.

Who We're Looking For

We are open to two profiles for this role:

The Experienced Rails Engineer

A senior full-stack engineer with deep Ruby on Rails experience and a track record of owning product features end-to-end in a product organization. You have been doing this long enough to shape problems, push back on scope, and ship without much hand-holding. AI tooling is part of your workflow and you are getting faster because of it.

The AI-Forward Engineer

3+ years of professional engineering experience, strong full-stack fundamentals, and genuinely elite command of AI coding tools — Claude Code, Cursor, Copilot, or equivalent. You are not just using these tools, you are building workflows around them and getting output that outpaces engineers with twice your tenure. You are eager to help a technical team level up their AI practices from the inside and excited to help shape what that looks like.

Both profiles are real and both will be considered. What does not work is someone who treats AI tooling as optional or is skeptical of it.

What You'll Do

• Own large product features end-to-end, from shaping the approach through delivery
• Break down ambiguous problem statements into clear technical changes
• Collaborate with product managers to clarify requirements and push back on scope when warranted
• Review PRs with an eye toward maintainability, not just correctness
• Write and maintain automated tests as a first-class responsibility
• Improve legacy areas of the codebase incrementally and pragmatically
• Use AI coding tools daily to increase throughput while remaining fully accountable for what you ship
• Help the broader engineering team develop stronger AI-assisted development practices

Tech Stack

• Backend: Ruby on Rails 8.1
• Frontend: React 18.3, Stimulus, Turbo
• Data: PostgreSQL, Redis
• Infrastructure: Heroku
• CI/CD: GitHub Actions
• Architecture: Modular monolith — engineers work across the full stack

Requirements

• 3+ years of professional software engineering experience
• Strong full-stack fundamentals with meaningful back-end experience
• Active, demonstrated use of AI coding tools (Claude Code, Cursor, GitHub Copilot) in a professional setting — not familiarity, actual fluency
• Track record of owning features end-to-end, not just clearing a queue
• Strong automated testing discipline
• Clear, proactive communication with product managers and cross-functional stakeholders
• US-based, authorized to work without sponsorship, and able to work Eastern timezone core hours

Nice to Have

• Ruby on Rails experience
• Experience with Stimulus and Turbo
• Background in early-stage, entrepreneurial, or startup environments
• Strong E2E testing practices
• ERP-style or complex domain modeling experience
• Domain experience in staffing, HR tech, or marketplace platforms
• New York area (optional in-office day available at Flatiron HQ)

Compensation & Benefits

• Base: $175,000–$200,000
• Equity: Offered
• Benefits: Medical, dental, and vision for employee and dependents; life and disability insurance; paid parental leave; work-from-home stipend; company-supplied Apple laptop; phone and internet stipend; uncapped PTO; paid office holidays; 401(k) through Fidelity