Senior Backend Engineer (Ruby), Plan: Spec-Driven Development

In this role you’ll drive the backend implementation for Plan: Spec-Driven Development, turning intents into actionable work items, plans, and mergeable code. You’ll own backend flows, APIs, data models, and evaluation systems, collaborating across product, design, and users toward a public beta. You’ll lead major features from concept to release, mentor peers, and shape technical direction in a fast-paced, async‑first, all-remote environment. You’ll work on high-visibility AI-enabled workflows that scale how teams build software.

• Flexible Paid Time Off
• Team Member Resource Groups
• Equity Compensation & Employee Stock Purchase Plan
• Growth and Development Fund
• Parental Leave

• Lead backend features from early product discussions through design, implementation, rollout, and post-launch learning
• Build flows, APIs, and data models behind agent-generated work items, implementation plans, durable specifications, and mergeable code
• Develop evaluation and benchmarking systems for workflow quality, token cost, and success rate
• Use Ruby on Rails and Python to build reliable production systems with PostgreSQL, GraphQL, and AI-related platforms
• Collaborate with product, design, engineers, design partners, and users to shape scope and trade-offs
• Coordinate multi-person projects in an asynchronous, all-remote environment
• Mentor other engineers and influence technical direction across the Plan group and AI initiatives
• Work in short iterations, share progress, and use feedback to guide next steps

• Strong Ruby on Rails experience in a large production codebase
• Production experience with Python
• Experience leading substantial projects over months with clear outcomes
• Product mindset with end-to-end ownership of features
• Full stack background with backend focus and ability to read frontend code
• Strong API design and SQL fundamentals
• Experience exploring AI-assisted development
• Ability to work independently and mentor others
• Experience with GraphQL, PostgreSQL performance, or large language model/agent systems is helpful but not required

• collaboration across functions and regions
• technical leadership and mentoring
• clear communication in asynchronous environments
• Ruby on Rails
• Python
• PostgreSQL