Head of Engineering

Trial Library•San Francisco, CA

2d•$228,000 - $285,000•Hybrid

About The Position

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.

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.

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.

Benefits

Comprehensive medical, dental, and vision coverage for employees and eligible dependents
Disability, life, and supplemental insurance options
Flexible paid time off
Observed company holidays
One-time home office stipend
401(k) program
Pre-tax HSA and FSA options
Commuter benefits
Financial wellness resources
Access to legal protection plans
Access to voluntary benefit offerings including pet wellness support
Domestic partner coverage
Additional programs that support the diverse needs of our team members and their families