Head of Engineering

Trial Library is an AI-native research platform with a mission to improve healthcare outcomes by expanding access to precision medicine. About Trial Library Trial Library is an AI-native enrollment and care navigation platform that accelerates access to precision medicine. In collaboration with biopharmaceutical manufacturers, payers, and health systems, Trial Library enables the delivery of clinical trials as a standard care option - improving patient access, advancing oncology outcomes, and reducing the total cost of care. Backed by leading healthcare venture capital firms, Trial Library’s platform is currently deployed in 840+ clinics and 3,000+ providers nationwide. 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. Why Trial Library Meaningful impact — helping patients access clinical trials faster through better technology and workflows High ownership environment — autonomy to build, test, and influence strategy across the business Collaborative team culture — low ego, high trust, and close partnership across functions Opportunity for growth — join at an early stage with meaningful exposure to company-building and decision-making Our Core Values Ally is our favorite moniker The broadest reach is worth the effort Celebrate measurable improvements in access and outcomes Fearless advocates for representation in research Incentives matter to stakeholders choosing our products Taking initiative is actually giving We are accountable for the experience of patients and providers Empathy and humility are the real dynamic duo Our Benefits & Perks Health & Wellness: Comprehensive medical, dental, and vision coverage for employees and eligible dependents, along with disability, life, and supplemental insurance options designed to support your overall well-being. Time Off & Workplace Support: Flexible paid time off, observed company holidays, and a one-time home office stipend to help you create a productive and comfortable remote workspace within our hybrid environment. Financial & Lifestyle Benefits:401(k) program, pre-tax HSA and FSA options, commuter benefits, financial wellness resources, and access to legal protection plans to support both short- and long-term planning. Additional Support & Voluntary Benefits: Access to voluntary benefit offerings including pet wellness support, domestic partner coverage, and additional programs that support the diverse needs of our team members and their families. Our Interview Process Our interview process typically includes four stages, followed by reference checks and an offer. Depending on the role, particularly for technical or senior positions, the process may vary slightly and can include a technical assessment, case study, presentation, practical exercise, additional interview conversations, or conversations with members of our leadership team and investors. Trial Library, Inc. is an equal opportunity employer committed to building an inclusive workplace. We provide equal employment opportunities to all employees and applicants and prohibit discrimination and harassment of any kind without regard to race, color, religion, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity or expression, national origin, ancestry, age, disability, genetic information, marital status, veteran status, military status, medical condition, family or medical leave status, political affiliation, or any other characteristic protected by applicable federal, state, or local law. Trial Library, Inc. is committed to providing reasonable accommodations for qualified individuals with disabilities throughout the recruiting process. If you require assistance or accommodation, please contact [email protected] We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.