Staff Software Engineer, Automations

About Plenful Plenful is on a mission to transform healthcare operations from the inside out. Fresh off our $50M Series B and backed by Bessemer Venture Partners, Notable Capital, TQ Ventures, Susa/Kivu Ventures, and other leading investors, we’re building the category-defining AI agentic operating platform that healthcare teams rely on to operate smarter, faster, and more efficiently. Our technology empowers healthcare operators across hospital and health systems, pharmacies and payors to eliminate manual work, reduce administrative burden, and improve compliance, all while unlocking critical revenue to fund programs for their in-need patient populations. Built by healthcare operators for healthcare operators, Plenful is driven by a deep understanding of the challenges facing today’s care teams. We’re passionate about equipping healthcare workers with world-class tools that deliver real, measurable impact, and we’re proud to serve leading healthcare organizations across the country. If you’re excited to help shape the future of healthcare, we’d love to meet you. Apply now to join our growing team. About the role We’re looking for a Staff Software Engineer to lead the design and development of systems that power our automations platform. In this role, you’ll take ownership of key components that will guide and shape the future of our entire platform. You’ll work closely with DevOps, ML/AI, Customer Success, and UX teams. You’ll also mentor engineers and help set technical direction across the organization. What you’ll do Core Infrastructure & Workflow Orchestration Maintain and evolve our workflow automation system that runs across serverless and containerized environments, processing millions of tasks each month. Design scheduling, queuing, rate limiting, and retry logic for reliable and fair resource allocation. Build mechanisms for state tracking, error handling, timeouts, and cleanup across distributed tasks. Partner with DevOps on observability, structured logging, tracing, and deployment automation. External Integrations & Data Pipelines Manage integrations with SFTP, email, databases, spreadsheets, and REST APIs, with secure credential and failure recovery handling. Build and maintain file processing pipelines that handle millions of files per month. Work with healthcare data formats (HL7, X12, EDI) and standard file types (PDF, Excel, CSV, JSON). Develop webhook handlers, polling services, and event-driven workflows to ensure data consistency. Collaborate with ML/AI teams on data pipelines for model training and inference. Technical Leadership Lead technical projects and set quality and reliability standards for the backend team. Identify and reduce technical debt; plan and execute major system improvements and migrations. Mentor engineers through code reviews, design sessions, and pair programming. Participate in incident response and postmortems, focusing on long-term reliability. Write and review RFCs to document and guide key architectural decisions. What we’re looking for 8+ years of professional software engineering experience. Strong background in distributed systems, workflow orchestration, automated systems, and event-driven pipelines at scale. Advanced database expertise: SQL, schema design, query tuning, and operations at scale. Solid computer science fundamentals (data structures, algorithms, system design). Experience building and maintaining large-scale data pipelines 3+ years of technical leadership, guiding projects and mentoring engineers. Track record of improving reliability, managing incidents, and reducing technical debt. Strong written and verbal communication skills for documentation and cross-team collaboration. Experience working closely with DevOps, observability, ML/AI, and UX teams. Plenful perks Comprehensive Benefits Package : Enjoy unlimited PTO, fully covered health insurance (medical, dental, and vision), meal stipend, health & wellness stipend, 401(k) matching, and stock options Missio