Principal Software Engineer

Plenful • San Francisco, CA

3h • Hybrid

About The Position

Plenful is hiring a Principal Software Engineer to architect and own the data foundation of Plenful’s next-generation automation platform. This role is singularly focused on building the institutional memory and context graph layer — a greenfield system that will power complex, multi-step workflows, decision tracing, and durable abstractions in a regulated healthcare domain. This is a foundational systems architect position, not a people-manager-first role. Your primary output is durable, scalable data architecture that other teams build on. You will design and ship the context graph + decision tracing system that becomes the backbone of Plenful’s automation platform. Key objectives include architecting the domain model, context graph, workflow state, actions, and decision history; defining how institutional memory is represented, versioned, queried, and evolved; building systems that are expressive enough for AI-driven workflows while remaining governed, testable, and auditable; ensuring the platform scales from approximately 90 customers today to 200+ without degrading reliability; and reducing hero-dependence by building abstractions that prevent constant escalations. The broader engineering team is scaling from 20 to 40 within a year, and the organization is moving from horizontal teams to feature-based teams with tech leads.

Requirements

• 12+ years owning data architecture in large-scale production systems.
• Deep relational database and distributed systems expertise.
• Strong experience evolving schemas in complex, regulated domains.
• Clear judgment on normalization vs. denormalization, performance tradeoffs, and system boundaries.
• Experience handling mission-critical incidents in production.
• Comfort operating in ambiguous, fuzzy problem spaces.
• Hands-on coding ability in a Python-heavy backend environment.
• Strong reliability instincts, including observability, testing, and QA rigor.

Nice To Haves

• Experience in healthcare, fintech, or infrastructure environments.
• Exposure to or experience with modern, scaled, high-throughput infrastructure environments such as Stripe, Brex, or Notion.
• Practical understanding of applied AI systems (not pure ML research).
• Comfort in customer-facing technical discussions.

Responsibilities

• Define the canonical data model for workflows, context, actions, and outcomes.
• Design durable abstractions across automation, decision tracing, and system memory.
• Establish clear system boundaries across feature-based teams.
• Architect a graph-backed representation of state, history, and reasoning.
• Enable traceability of decisions across complex healthcare workflows.
• Ensure schema evolution supports regulatory scrutiny and auditability.
• Design state management systems across AWS, Postgres, Python, and Temporal workflows.
• Drive performance, reliability, and scalability across high-throughput workflows.
• Own normalization tradeoffs, indexing strategy, and access pattern design.
• Establish standards for schema versioning, lineage, testing, and data integrity.
• Build systems that reduce incident frequency and escalation dependency.
• Partner with tech leads across feature teams to enforce architectural coherence.

Benefits

• Unlimited PTO
• Fully covered health insurance (medical, dental, and vision)
• Meal stipend
• Health & wellness stipend
• 401(k) matching
• Stock options
• Opportunities for Growth: Strengthen your partnership expertise through collaboration with experienced, high-performing leaders across the organization
• Flexible Hybrid Work Environment

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Education Level: No Education Listed