Head of Engineering

About the jobHead of EngineeringLocation: Seattle, WA, Full-TimeWe're hiring a Head of Engineering to reinvent how legal work gets done in the age of AI.Boundless is a Series C legal tech company based in Seattle, backed by Pioneer Square Labs, Trilogy, Foundry Group (Brad Feld) and Silver Lake. We operate in 10+ countries and have helped over 100,000 people and companies navigate immigration. We build tech-powered immigration solutions for two audiences: corporate HR teams managing high volumes of employer-sponsored cases, and individuals navigating family and naturalization cases. We have in-house lawyers and are building a world-class AI-powered services firm. Anthropic is not coming for this. Immigration is vertical, regulated, and workflow-deep, and we are racing to build the defining AI product in the category.Why this role existsWe are rebuilding our software platform and engineering infrastructure from the ground up, and we need a Head of Engineering to lead the team.You will inherit a real customer base, a real platform, and a great team of engineers. Immigration is complex, with endless edge cases and global scale. We are building intelligent automation, orchestration, and decision-making to support the agentification of legal workflows, with the checks and balances required to ensure accuracy in a regulated domain and to enable the lawyers who ultimately own legal decisions. The engineering challenge is a team and a system that can handle this complexity without sacrificing accuracy, observability, or speed, at the scale required to reliably serve thousands of people every year.However, this is not a caretaker role. The world is changing around us and the team is in the midst of transitioning to both an AI-native customer product and an AI-native development process. You will need to drive change with us, and partner with our existing engineering, product, design, legal and operations teams to build a world-class AI-native platform for legal services, and continue to evolve our development infrastructure towards being a truly AI-native “software factory”.We are looking for someone who can hold the whole picture: the customer, the team, the platform, the AI layer, the delivery system - and how they interact. Someone who makes hard calls, thinks in years not months, and builds an organization that top-tier engineers find exciting and satisfying to be part of. We are a remote-first team with a small in-person office in Seattle. We want someone based in Seattle and expect you to be in the office a minimum of 2-days per week.What you will doBuild the team. Retain our top performers, hire more top-tier engineers, and lead, inspire, challenge, level, structure, and grow the team. Own engineering delivery end to end. Roadmap execution, quality, on-call, and the operational health of a platform that customers depend on daily.Evolve team design as the work changes. Service boundaries and team boundaries move together. You’ll be a true player-coach: expected to ship code yourself while leading the team and staying close to the details of everything we build. Drive the AI transition through the team, not around it. Every engineer should be building with LLMs, retrieval, and structured tools as a default.Build the foundational infrastructure that operating teams use to deploy, monitor, and manage agents and LLM-powered customer features at enormous scale. Continue our transition towards a “software factory” engineering model, overhauling dev processes, systems, tools, and culture.Partner with product, design, legal and operations as a peer. Engage thoughtfully in tradeoff conversations about scope, sequencing, and what "done" means in a regulated domain.Set the technical bar in design reviews and hard tradeoff conversations. Make sure architecture decisions get written down and give the team durable context. Help us build a platform that both engineers and operating teams pine for after they leave.Grow engineers into architectural thinking by giving them opportunities to step up, and pushing their thinking constructively. Who you areYou are a builder. You set new benchmarks for output and want a role where your team ships with autonomy and speed. Not a role where you wait for consensus.You have 10+ years in engineering and 4+ years managing engineers, including managing managers or senior ICs. You move fast by making decisions quickly, not by cutting corners. You know the difference between a reversible call and one that will come back to haunt us. You hire well and manage out when you need to. You have built a team you were proud of and you can describe what made it work.You have shipped AI into production and led a team through the shift. You have views on retrieval, evaluation, latency, and where LLMs break down, and you know when to use AI and when another tool is the right call.You have been the technical decision-maker, not just the person who runs the process. You can lead a design review and change the answer.You think in systems. You can hold the team, the platform, the AI layer, and the business constraints in your head at once and see where they don't line up.You have taste. You can build teams and systems where agents and humans work in harmony without overbuilding.You have worked in a domain where correctness has consequences: legal, healthcare, financial services, or public safety. You understand why accuracy and auditability are non-negotiable.Good signals, not requirementsYou have worked at both large and small companies and have a preference for small. You understand speed to impact but also know what matters at scale.Founder or CTO experience.You have scaled a team through a platform rebuild or replatforming, and can talk about what you got wrong.Experience with workflow automation.Prior work with vector search, semantic retrieval, or document understanding systems at production scale.BenefitsHealth InsuranceDental InsuranceVision Insurance401(k) MatchingPaid Time Off (PTO)Paid HolidaysSick LeaveRemote WorkFlexible ScheduleLife InsuranceParental LeaveProfessional DevelopmentBonusPreferred SkillsPlatform ArchitectureSystem ArchitectureData InfrastructureAPI DesignLLMAI AgentsAgentic WorkflowsRAG