Principal Engineer

Paperless Parts•Boston, MA

3h•$212,000 - $286,000•Hybrid

About The Position

Step into the role of Principal Software Engineer and serve as a technical force multiplier for our engineering organization. In this high-leverage position, you will look beyond the immediate roadmap to define the architectural vision that will support Paperless Parts for years to come. You will bridge the gap between business strategy and technical execution, ensuring our systems are robust, scalable, and AI-ready. This role is a powerful catalyst for change and innovation. You will be responsible for modernizing our engineering practices—integrating AI agents into the development lifecycle, driving the evolution from monolithic to a service architecture, and mentoring our engineers to become the next generation of leaders.

Requirements

12+ years of experience in software engineering, with a strong background in architecting SaaS products at scale (start-up to scale-up transition experience preferred).
Deep Architectural Expertise: Proven success decomposing monoliths and designing distributed systems, with strong judgment on build-vs-buy decisions and technology selection.
Modern Stack Proficiency: Expert-level knowledge of modern web frameworks and databases, along with deep experience in AWS cloud-native patterns (containers, serverless).
AI/LLM Fluency: Practical experience leveraging LLMs and AI agents in a production engineering workflow. You understand prompt engineering, context limits, and how to structure codebases for AI interpretability.
Operational Rigor: A strong commitment to production reliability, with experience designing systems for observability and leading incident response processes.
Communication Mastery: Exceptional ability to communicate complex technical concepts to non-technical stakeholders and influence decisions without relying on authority.

Responsibilities

Architect & Evolve: Lead the technical strategy for migrating legacy monolithic patterns to scalable, service architectures. You will define the long-term vision for our backend systems, APIs, and cloud infrastructure.
Operationalize AI Development: Drive the adoption and continuous improvement of AI-assisted workflows (using tools like Cursor and Claude Code). You will champion the strategic integration of AI agents to enhance autonomous task execution and leverage AI throughout the software life cycle.
Drive Operational Maturity: Instill a strong focus on reliability and site operations across the team. You will lead initiatives to improve observability (logging, monitoring), define clear runbooks, and facilitate postmortems that turn incidents into structural improvements.
Elevate Engineering Standards: Enforce "context-first" engineering. You will champion the creation of Architectural Decision Records (ADRs) and high-quality documentation, ensuring our codebase provides the explicit context needed for both human alignment and effective AI agent performance.
Mentor & Lead: Act as a technical beacon, dedicating significant time (~20%) to pairing, design reviews, and mentoring engineers across different levels to elevate the team's collective skill set.
Strategic Alignment: Collaborate with R&D leadership to prioritize technical initiatives. You will articulate the ROI of infrastructure investments and technical debt reduction in terms of customer reliability and business agility.