Staff Software Engineer, AI-Native Engineering

This is a fully remote position, open to applicants in Massachusetts.

📋 Description

• Oversee the design and implementation of intricate, cross-functional features from architecture to production operations.

• Develop AI-native functionalities, which include agent loops, tool utilization, prompt and context design, retrieval, and evaluation harnesses.

• Establish and promote AI utilization in code generation, test automation, review, triage, and documentation.

• Assess the impact of AI-assisted and agentic development, sharing best practices.

• Provide mentorship to senior and mid-level engineers.

• Set benchmarks for code quality, observability, and the safe application of AI technologies.

• Collaborate with product, UX, and engineering leaders to transform unclear challenges into well-defined, actionable plans.

• Take ownership of production quality, encompassing defect triage, release readiness, and gate reviews.

⛳️ Requirements

• Experience in leveraging or critically evaluating the integration of AI into workflows, decision-making, or problem-solving.

• Current, hands-on expertise in AI-assisted and agentic development.

• 8+ years of experience in software engineering.

• Proven track record of technical leadership at the staff level or comparable position.

• Strong skills in TypeScript or another statically typed programming language.

• Robust system design capabilities.

• Practical experience in building or integrating LLM-based features, including prompt design, retrieval, context management, evaluation, and cost/latency considerations.

• Familiarity with agentic architectures, incorporating tool usage, orchestration, and human-in-the-loop controls.

• Excellent written and verbal communication skills, including the ability to brief senior leaders and coordinate across multiple teams.

• Knowledge of enterprise SaaS, multi-tenant systems, and secure, compliant software delivery.

🏝️ Benefits

• Equity (when applicable).

• Variable/incentive compensation.

• Health plans.

• Flexible spending accounts.

• 401(k) Plan with company match.

• Employee Stock Purchase Plan (ESPP).

• Matching donations.

• Flexible time away plan.

• Family leave programs.