Director of Engineering

Location: Remote, US-based. Full Time. Mandatory Eastern time zone hours, or Central at minimum. About the Role Every day, pet parents walk out of a vet’s office having just said no to a treatment their pet needed, not because they don’t love their pet, but because they couldn’t afford care. Pawlicy Advisor exists to eliminate this problem. Pawlicy Advisor is a venture-backed startup building the infrastructure that connects pet parents to the right financial protection for their pets, starting with the most trusted pet insurance marketplace in the US, distributed through thousands of veterinary practices nationwide. Pawlicy Advisor has delivered over 1 million unique quotes, has raised $19M+, has found product-market fit, and is now scaling. Pawlicy Advisor is hiring a Director of Engineering to lead the engineering organization and own how it builds: technical strategy, architecture, quality, security, delivery, and the growth of the engineering team. This is a hands-on role at a profitable business where you will set the bar for how the team builds, including how the company uses AI tools. The role reports directly to the Chief Product Officer and leads an outstanding team of engineers working alongside a senior product manager, senior product designer, and data analyst. What You Own Technical Leadership Key architectural decisions: major tech choices, build vs buy, scalability of the site, and carrier integrations. Security reviews of product and infrastructure changes, plus carrier and vendor security questionnaires and audits. Serving as the technical point of contact and leader with key partners. Release management and deployment: CI/CD, release cadence, rollbacks, and production stability. Prioritizing technical debt and refactoring, balanced against feature velocity. QA and testing processes: automated coverage, manual QA, and quality standards before release. Engineering Management On-call management: rotation, escalation paths, incident response, and postmortems. Career development of engineers: 1:1s, performance feedback, and keeping the team unblocked. Building the team: hiring and onboarding new engineers as the company grows. Vendor and AI Management Approval of new software used internally, evaluated on cost, security, and fit, including renewals and replacements. Engineering tooling and infrastructure spend: cloud costs, licenses, and consolidation opportunities. Owning and evolving Pawlicy’s AI policy and best practices. Lead the company’s rollout and expansion of AI usage while optimizing cost. Where You Partner OKRs: creation and ownership of key business goals and objectives Product: sprint priorities, tech debt vs feature velocity tradeoffs, and delivery timelines with the senior product manager and the Chief Product Officer. Design: front end quality and design QA with the senior product designer. Partnerships and legal: carrier and vendor security questionnaires, audits, and integration requirements. Data and analytics: tooling and reliable data flow across product systems What Success Looks Like First 90 days Delivery is stable and predictable: releases ship on a defined cadence, and incidents have owners, escalation paths, and postmortems. Full command of the architecture: the site, quote engine, and carrier integrations, with a prioritized view of technical debt and risk. 1:1s and career development running for every engineer. A first version of Pawlicy’s AI development policy and best practices in place. First 12 months A technical roadmap has been executed with security investments sequenced against business priorities. Delivery measurably improved: velocity, quality, and production stability all trend the right way. Carrier and vendor security reviews handled end to end without external help. Engineers are growing against clear development plans, and the team is confident in the technical bar you set. AI-assisted development is ingrained in the culture and adopted with measured results. 10+ years of software engineering experience, including 5+ years managing engineers and 2+ years in a senior engineering leadership role (Director, or senior-most technical leader), ideally at an early stage startup or fast-moving environment. The stack: TypeScript, Next.js, Node, GraphQL, Postgres, AWS. Proven technical ownership and leadership: you have owned the technical strategy, architecture, and roadmap for a production consumer product, and built or scaled the team that delivered it. Still hands-on: comfortable reviewing PRs, reading code deeply, and jumping into an incident. Experience with application security and third-party compliance: security reviews, vendor questionnaires, and audits. Track record of excellent cross department communication and relationships leading to business success Practical enthusiasm for AI-assisted development. Legally authorized to work in the United States without sponsorship. Preferred: experience in insurance or fintech, or with partner API integrations. Extra points if you love animals and believe pet healthcare is a serious, underserved problem. How You Work You set your own technical agenda: there is no CTO above you defining priorities, and you generate the roadmap rather than execute one handed down. You fix things nobody asked you to fix: architecture, process, or tooling.. You enjoy teaching non-technical colleagues and working with cross functional teams. You push back, disagree, and align without it becoming political. You lead from the front with AI tool adoption and usage and evangelize across the company AI and the Hiring Process We embrace AI at Pawlicy and our work still relies on what the humans bring to it. So please leave the AI out of interviews and case studies. Prep with it all you like, but in the room, we want your thinking, your questions, your judgment. These stages exist so we can get to know you and how you’d work with our team. We’re hiring you, not a model and it is you we want to see. To be concrete: no AI assistants or chatbots on any device during your interviews, and nobody else feeding you answers. Spell-check, autocomplete and notes you wrote yourself are all completely fine. If it turns out AI was used where we’ve asked you not to, it may end your candidacy. If any part of our process is a barrier because of how you read, write or communicate, email [email protected] before that stage and we’ll talk through the options. The skills we’re assessing stay the same; what changes is the format. Asking has no bearing on how we assess you. Base salary range: $215,000 - $240,000 Startup equity grant. Top-tier medical, dental, and vision insurance; 401(k) employer contributions; flexible vacation. Remote-first within the United States. Career Path This role is scoped as Director of Engineering and is the senior-most technical seat at the company, with a path to VP of Engineering as the team grows from ~20 today to 25-30 in 2027. Founded in 2018 and headquartered in NYC, Pawlicy Advisor is a licensed insurance agency and the leading pet insurance marketplace in the US. If you want real technical ownership, thrive in a fast paced environment, and care about developing engineers, Pawlicy would like to talk. Learn more at https://www.pawlicy.com/about-us/