Senior Software Engineer

Workforce.com; Chicago (IL); On-site; USD 120,000 - 170,000; Full time

Benefits offered by this job

Real problems solved

Long-form planning

Autonomy and ownership

Competitive compensation

Job summary

Workforce.com is seeking a Senior Software Engineer with Ruby experience to ship high-impact work quickly. You’ll collaborate with Sales, Product, and Customer Success to ensure the right solutions are built the right way.

Our team works in Shape Up cycles, solving big problems end-to-end in an on-site Chicago role. You’ll mentor others and contribute to backend systems, APIs, and occasional frontend work as needed.

Qualifications

• 5+ years of Ruby experience.
• Ability to deliver large features independently.
• Experience with Rails, PostgreSQL, Redis, and REST APIs.

Responsibilities

• Build robust, maintainable systems with Ruby and Rails.
• Own backend systems and APIs; contribute to frontend/infrastructure when needed.
• Lead development through scoping, building, testing, and deploying.
• Review code and mentor engineers; improve codebase quality.

Skills

Ruby

Rails

System design

Communication

AWS

CI/CD

REST APIs

Tools

Docker

PostgreSQL

Redis

Job description

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