Staff Software Engineer

About Plenful Plenful is on a mission to transform healthcare operations from the inside out. Fresh off our $50M Series B and backed by Notable Capital, Bessemer Venture Partners, TQ Ventures, Susa/Kivu Ventures, and other leading investors, we’re building the category-defining AI workflow automation 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 90+ leading health systems 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 Plenful is hiring a Staff Software Engineer to lead the design and development of systems that power our automations platform. In this role, you'll own key components that shape the future of our entire platform. You'll work closely with DevOps, ML/AI, Customer Success, and UX teams, and mentor engineers while helping set technical direction across the organization. This role is hybrid. 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 a month. Design scheduling, queuing, rate limiting, and retry logic for reliable, 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 a 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 that keep data consistent. 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, with a focus on long-term reliability. Write and review RFCs to document and guide key architectural decisions. You May Be a Fit If You've spent 8+ years in professional software engineering. You have a strong background in distributed systems, workflow orchestration, automated systems, and event-driven pipelines at scale. You have advanced database expertise: SQL, schema design, query tuning, and operations at scale. Your computer science fundamentals — data structures, algorithms, system design — are solid. You've built and maintained large-scale data pipelines. You've spent 3+ years in technical leadership, guiding projects and mentoring engineers. You have a track record of improving reliability, managing incidents, and reducing technical debt. You communicate clearly in writing and in conversation, for documentation and cross-team collaboration. You've worked closely with DevOps, observability, ML/AI, and UX teams. Why You'll Love Working Here 🚀 Mission-Driven, World-Class Team — Join an exceptional group of professionals aligned around a meaningful mission and committed to making an impact 📈 Opportunities for Growth — Strengthen your expertise through collaboration with experienced, high-performing leaders across the organization 🏢 Flexible Hybrid Work Environment — We're remote-first, with meaningful office presence in San Francisco and New York. R&D roles follow a hybrid model, with two days per week in our San Francisco office Benefits & Perks 🏥 Healthcare Coverage — Full medical, dental, and vision insurance for you and participation for your family 💰 401(k) with Company Match — Plenful matches 50% of your first 3% contributed 📊 Equity — Every full-time employee shares in our success 🌴 Unlimited PTO — Take the time you need, when you need it 🍽️ Daily Lunch Stipend — $100/week to cover your midday meals 💪 Wellness Stipend — $100/month to support your health and well-being 🚇 Commuter Benefits — $100/month for SF and NYC-based employees 👶 Parental Leave — Paid leave to support growing families