Senior Software Engineer

About the job

We're looking for a Senior Software Engineer with Ruby experience who's driven to ship high-impact work quickly. At Workforce.com, engineers move fast, solve real problems, and collaborate closely with other teams — including Sales, Product, and Customer Success — to ensure we're building the right things, the right way.

We use the Shape Up methodology by Basecamp, working in focused 8-week cycles to deliver meaningful value without the overhead of daily stand-ups or micro-management. You'll take on big, complex problems and help shape the solution — then work end-to-end to deliver it.

This role is on‑site in Chicago five days per week.

What You’ll Do

Full‑Stack Engineering with Ruby Focus

• Use your strong Ruby and Rails experience to build robust, maintainable systems.
• Own backend systems and API layers, with the flexibility to contribute to frontend or infrastructure when needed.
• Contribute across all stages of the development cycle: scoping, building, testing, and deploying.

Fast, Practical Problem Solving

• Turn months‑long ideas into tangible value within 8‑week delivery cycles.
• Collaborate closely with the Product team to scope projects that are ambitious but realistic.

Technical Leadership & Mentorship

• Review code deeply and give meaningful, constructive feedback.
• Mentor less experienced engineers and lead by example through clear thinking and strong delivery.
• Continuously improve the quality, structure, and clarity of the codebase.

What We’re Looking For

• Extensive Ruby experience required (5+ years)
• Proven ability to deliver large, complex features independently
• Exposure to cloud platforms (AWS, Docker, CI/CD pipelines)
• Strong system design skills and product thinking
• Clear communicator, comfortable collaborating across roles and functions
• Experience with Rails, PostgreSQL, Redis, and REST APIs is a plus

Bonus Points

• Familiarity with the Shape Up methodology (or interest in learning it)
• Experience working in a SaaS environment or workforce management tools
• Some frontend experience (React or similar) is helpful, but not required

Why Workforce.com

• Work on real problems used by real businesses — and see the impact of your work
• High‑trust environment with long‑form planning, deep work, and no daily stand‑ups
• Strong engineering culture built on autonomy, ownership, and quality
• Competitive compensation and a flexible work environment