Director of Engineering

May 28, 2026

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About TRUE TRUE Property Insurance is a reciprocal insurer founded in 2020 to serve homeowners in storm-prone regions, starting in Florida and expanding across the country. TRUE delivers reliable homeowners coverage in complex risk environments and is actively scaling its underwriting and platform capabilities to support that mission. The company works with a network of distribution partners to bring its products to market and is continually expanding its homeowners offerings and geographic footprint. With a strong foundation in place, TRUE is in the midst of an exciting period of growth and is adding to its team to help drive the next stage of expansion. <h3 style="margin: 10pt 0in 0in; line-height: 105%; break-after: avoid; font-size: 10.5pt; font-family: Calibri, sans-serif; color: rgb(79, 129, 189); font-weight: bold;"> </h3> <h3 style="margin: 10pt 0in 0in; line-height: 105%; break-after: avoid; font-size: 10.5pt; font-family: Calibri, sans-serif; color: rgb(79, 129, 189); font-weight: bold;">Position overview</h3> The Director of Engineering is a hands-on leader responsible for getting engineering work delivered—on time, with quality, and with clear visibility. This role turns defined business priorities into realistic plans, clear milestones, and dependable releases. Reporting to the CTO, you’ll work within an established engineering platform, building on what’s already in place rather than starting from scratch. You’ll partner closely with Architecture/Technical Leadership, DevOps/SRE, Data Engineering, and Cybersecurity. While those teams own platform direction and technical standards, you ensure execution is coordinated across teams, dependencies are managed, and delivery stays aligned with business goals. <h3 style="margin: 10pt 0in 0in; line-height: 1.5; break-after: avoid; font-size: 10.5pt; font-family: Calibri, sans-serif; color: rgb(79, 129, 189); font-weight: bold;"> </h3> Responsibilities <ul style="margin-bottom: 0in; margin-top: 0px;"> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.2;"> Own delivery outcomes for approved initiatives, including scope, timelines, milestones, and release readiness </li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Translate business objectives into executable work: epics, stories, sequencing, staffing, and incremental releases</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Lead core execution rituals (planning, grooming, standups, demos, retros) to drive consistency and predictability</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Proactively manage risks, dependencies, and blockers; escalate early with clear options and tradeoffs</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Partner with Product and business stakeholders to clarify requirements, priorities, and success metrics</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Provide clear, transparent delivery reporting on progress, risks, and timeline confidence</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Ensure alignment with existing architecture, platform standards, and non-functional requirements</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Coordinate release readiness, environments, observability, and operational handoffs with DevOps/SRE</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Reinforce strong engineering fundamentals: code reviews, testing discipline, quality standards, and continuous improvement</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Lead and develop engineers and engineering leaders across multiple teams or workstreams</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Stay close to execution by reviewing designs, participating in code reviews, and unblocking critical initiatives</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Evaluate and negotiate vendors for delivery tools and services, partnering with Finance, Procurement, and Legal</li> <li style="margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px; line-height: 1.3;">Use AI tools responsibly to accelerate delivery while maintaining engineering quality and standards</li> </ul> <h3 style="line-height: 1.5; margin: 10pt 0in 0in; break-after: avoid; font-size: 10.5pt; font-family: Calibri, sans-serif; color: rgb(79, 129, 189); font-weight: bold;"> </h3> <h3 style="margin: 10pt 0in 0in; break-after: avoid; font-size: 10.5pt; font-family: Calibri, sans-serif; color: rgb(79, 129, 189); font-weight: bold;">Qualifications</h3> <ul style="margin-bottom: 0in; margin-top: 0px;"> <li style="margin: 0in 0in 0in 0px; font-size: 10.5pt; font-family: Calibri, sans-serif;">Bachelor’s or Master’s degree in Computer Science or equivalent experience</li> <li style="line-height: 1.3; margin: 0in 0in 0in 0px; font-size: 10.5pt; font-family: Calibri, sans-serif;">8+ years in an engineering leadership role delivering complex software initiatives end-to-end</li> <li style="line-height: 1.3; margin: 0in 0in 0in 0px; font-size: 10.5pt; font-family: Calibri, sans-serif;">P&C insurance domain experience required; homeowners insurance experience preferred</li> <li style="line-height: 1.3; margin: 0in 0in 0in 0px; font-size: 10.5pt; font-family: Calibri, sans-serif;">Experience leading large, multi-team engineering organizations</li> <li style="line-height: 1.3; margin: 0in 0in 0in 0px; font-size: 10.5pt; font-family: Calibri, sans-serif;">Vendor evaluation and contract negotiation experience</li> <li style="line-height: 1.3; margin: 0in 0in 0in 0px; font-size: 10.5pt; font-family: Calibri, sans-serif;">Proven track record of predictable delivery and strong stakeholder alignment</li> <li style="line-height: 1.3; margin: 0in 0in 0in 0px; font-size: 10.5pt; font-family: Calibri, sans-serif;">Proficiency in Java, AWS, and Agile delivery practices</li> <li style="line-height: 1.3; margin: 0in 0in 2pt 0px; font-size: 10.5pt; font-family: Calibri, sans-serif;">Strong understanding of cloud platforms and modern DevOps/SRE collaboration</li> </ul> <h3 style="line-height: 1.5; margin: 10pt 0in 0in; break-after: avoid; font-size: 10.5pt; font-family: Calibri, sans-serif; color: rgb(79, 129, 189); font-weight: bold;">Skills & Attributes</h3> <ul style="margin-bottom: 0in; margin-top: 0px;"> <li style="line-height: 1.5; margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px;">Strong execution mindset with disciplined planning and follow-through</li> <li style="line-height: 1.2; margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px;">Clear, direct communicator who avoids surprises</li> <li style="line-height: 1.2; margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px;">Pragmatic, collaborative leadership style</li> <li style="line-height: 1.2; margin-right: 0in; font-size: 12pt; font-family: 'Times New Roman', serif; margin-left: 0px;">Comfortable operating in a fast-moving environment with high delivery expectations</li> </ul> The role is primarily remote, but we offer an opportunity to work in an office environment in downtown Boston, MA, or in St. Petersburg, FL.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

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This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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