Trial Library is seeking an experienced Head of Engineering to lead our engineering organization and build the next generation of our AI-native platform. You will lead Engineering and Infrastructure while partnering closely with Product to deliver secure, scalable, and high-performing software. This is a hands-on leadership role for an engineering leader who enjoys solving complex technical challenges, building production AI systems, and mentoring exceptional engineering teams in a fast-paced startup environment. You'll help shape the technical direction of our platform while remaining deeply engaged in architecture, engineering execution, and technical decision-making. Your Responsibilities: • Lead and scale Trial Library's Engineering organization, fostering a collaborative and high-performing culture. • Partner with Product to translate business and customer needs into scalable technical solutions. • Own software architecture, engineering execution, platform reliability, and technical delivery. • Lead application engineering, AI engineering, infrastructure, DevSecOps, IT, and platform operations. • Design and build cloud-native systems supporting AI-powered products, including LLM applications, retrieval-augmented generation (RAG), AI agents, model evaluation, and production inference services. • Drive engineering excellence through modern software development practices, CI/CD, testing, observability, and operational excellence. • Build resilient, scalable infrastructure capable of supporting rapid product growth and evolving AI workloads. • Recruit, mentor, and develop high-performing engineering teams while creating an environment of continuous learning. • Partner cross-functionally with Clinical, Customer Success, Commercial, and Operations to deliver reliable customer experiences. • Ensure platform security, privacy, and compliance with HIPAA and SOC 2 requirements. • Balance engineering velocity with scalability, reliability, maintainability, and long-term technical health. • Stay current on emerging AI technologies and engineering best practices to continuously improve our platform. Your Requirements: • 8+ years of progressive software engineering experience, including engineering leadership in startup or high-growth environments. • Experience leading engineering teams responsible for building and scaling SaaS platforms. • Strong technical background in distributed systems, cloud-native architecture, APIs, and modern software engineering practices. • Experience building and operating production AI systems using large language models (LLMs), retrieval-augmented generation (RAG), AI agents, machine learning infrastructure, or related technologies. • Experience designing scalable cloud infrastructure on AWS, GCP, or Azure, including Kubernetes, CI/CD, infrastructure automation, and observability. • Demonstrated success recruiting, mentoring, and growing high-performing engineering teams. • Ability to balance rapid product delivery with platform reliability, security, and long-term maintainability. • Excellent communication skills with the ability to collaborate across departments • Experience within healthcare, life sciences, clinical research, or another regulated industry is preferred. • Familiarity with FHIR, HL7, HIPAA, and SOC 2 is a plus. $228,000 - $285,000 a year Compensation & On-Site Requirement This is a hybrid role based in San Francisco, CA, with a requirement of three days per week in the office (Wednesday, Thursday, & Friday). The salary range for this position is $228,000-$285,000 per year, plus performance incentives and equity, and reflects a good faith estimate of base pay for candidates working in this location. Final compensation will be based on experience, skills, qualifications, and network depth relevant to the role.