Engineering Director

Bestow • Dallas, TX

7d • $225,000 - $280,000 • Remote

About The Position

The Director of Engineering for Insurance Product Configuration & Enrollment Platform Core will be a highly technical, strategic engineering leader who is comfortable owning outcomes that span teams you manage and teams you do not. You are comfortable leading cross-team initiatives, even with teams who do not report to you. You understand distributed systems deeply, you can hold a firm line on quality in a regulated domain, and you are energized by building the managers and engineers on your team.

This role reports to the VP of Engineering, manages a group of Engineering Managers, and is open to Remote (US).

Requirements

• Bachelor's degree or equivalent experience.
• 8+ years of professional software development experience.
• 5+ years of progressive engineering management experience, including managing managers. You will lead 2–3 Engineering Managers and roughly 20–30 engineers across multiple teams.
• Proven ability to design, build, and operate distributed systems and microservices architectures at scale, including event-driven and event-sourced designs.
• Extensive experience with relational databases, particularly PostgreSQL, including schema design, data modeling, and query performance.
• Strong background in Golang and/or Python backend services, API design (gRPC, REST), and asynchronous messaging patterns.
• Strong advocate for agentic engineering, who has recently transformed at least one team to fully embrace agentic engineering
• Deep expertise across the software development lifecycle — inception, design, planning, delivering, continuous delivery, release strategy, monitoring, and continuous improvement.
• Credible across adjacent boundaries you do not own. You can reason about the frontend composition layer, data platform, and infrastructure well enough to negotiate interfaces, review designs, and resolve cross-team failures without escalating everything.
• Ability to 'go deep' technically when it matters. You can contribute changes to your teams' codebases and engage credibly in architectural decisions at any time.
• Advocate for automated testing and test-driven development, with real opinions on how to test configuration and rules at scale.
• Experience with cloud platforms, with a preference for Google Cloud Platform and Kubernetes.
• Ability to define and track key metrics, drive accountability across teams, and consistently meet committed dates and SLAs.
• Highly organized, with a demonstrated ability to manage competing priorities across multiple teams and partner commitments at once.
• Proven ability to attract, hire, mentor, and retain top-tier engineering talent, including developing senior engineers and early-career managers.
• Excellent written and verbal communication. You can explain a complex system and its trade-offs to an executive, a carrier partner, and an engineer in the same day.

Nice To Haves

• Life insurance, annuities, or other regulated-industry experience is a strong plus, as is experience delivering implementations for enterprise or carrier partners under contractual dates.

Responsibilities

• Define and drive the technical vision for your teams Core, and make sure it ladders up to Bestow's platform strategy and business objectives.
• Push configuration-driven repeatability over bespoke per-partner work, so that each new carrier implementation costs less and ships faster than the last.
• Provide architectural guidance and oversight across the configuration layer, the enrollment workflow engine, and the event-sourced domain services, keeping them scalable, reliable, secure, and performant.
• Lead initiatives whose success depends on teams that do not report to you, and make measurable impact at the vertical and org level rather than only inside your own scope.
• Own the interfaces between your teams and the ones you depend on and resolve ambiguity about ownership before it becomes an incident or a slipped date.
• Represent Bestow credibly with carrier partners, vendors, and other technology companies, including in technical due diligence and vendor negotiations.
• Stay current with emerging technologies and evaluate honestly what belongs on our platform.
• Foster a culture of technical excellence, innovation, and continuous learning, in partnership with our Principal engineers and other engineering leaders.
• Own your teams' delivery commitments to carrier partners, including UAT handoff dates, and represent that status accurately to executive leadership.
• Head off requirements churn at the source. Partner with Product, Delivery Management, Underwriting, and Compliance to surface missing requirements and cross-team dependencies during discovery, when a gap costs a conversation rather than a release.
• Own your organization's incident posture. Drive urgency and priority grading, insist on real root-cause analysis, look across incidents for systemic causes, and close the loop on follow-up actions.
• Hold the principle that the team owning a service owns its operation, including the supporting infrastructure, and work with platform engineering to make that practical rather than nominal.
• Ability to build a testing strategy that scales with the rules and configuration we ship — automated coverage, human-readable outcomes for underwriting and compliance reviewers, and repeatable regression runs in place of thousand-case manual test fests.
• Champion data and metrics for technical decisions, system health, and the impact of engineering investment.
• Translate business requirements and partner roadmaps into clear technical strategies and staffing plans, balancing near-term commitments against long-term maintainability and security.
• Lead, mentor, and grow a group of Engineering Managers, and build the leadership bench under them.
• Build, nurture, and scale high-performing teams with a strong sense of ownership, accountability, and psychological safety.
• Run performance management with rigor: career ladder expectations, scorecards, calibration, direct feedback, personalized growth plans, and prompt action on individual or team challenges.
• Maintain bench depth and knowledge redundancy so that a single departure or absence does not put a partner commitment at risk.
• Act as hiring manager for your organization's open requisitions. Own the funnel with recruiting, participate in the hiring cadence, and raise the bar with every hire.
• Manage our contractor and vendor partners as part of one team — same expectations, same calibration, same quality bar as our full-time engineers.
• Establish engineering processes and ceremonies that make teams faster, and remove the ones that do not.
• Direct the adoption of AI-augmented development in your organization rather than delegating it. Set the strategy for where AI changes how we build, and hold your teams to it.
• Drive adoption of AI development tooling (Claude Code, Claude Tag, GitHub Copilot) and AI-first delivery practices such as AIDLC across your teams, and measure whether adoption is producing real leverage.
• Establish standards for AI-generated code — review requirements, automated testing, and documentation workflows — that reduce technical debt instead of accelerating its creation.
• Partner with Security, IT, and Compliance to expand what AI tooling we can safely use, proposing compensating controls rather than stopping at a blocked request.
• Coach engineers and managers against the AI competencies in our career ladders, and evaluate for them when you hire and when you calibrate.
• Build leverage with AI instead of consuming engineering capacity. Turn recurring questions from Product, Design, and new engineers into durable, self-serve knowledge.

Benefits

• Competitive salary and equity based on role
• Policies and managers that support work/life balance, like our flexible paid time off and parental leave programs
• 100% paid-premium option for medical, dental, and vision insurance
• Lifestyle stipend to support your physical, emotional, and financial wellbeing
• Flexible work-from-home policy and open to remote
• Remote and WFH options, as well as a beautiful, state-of-the-art office in Dallas’ Deep Ellum, for those who prefer an office setting
• Employee-led diversity, equity, and inclusion initiatives

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: Associate degree