Director of Engineering for Insurance Product Configuration & Enrollment Platform Core

ABOUT THE TEAM

The Engineering team is the core of Bestow, driving all technology for our SaaS platform that empowers insurance carriers. We build and operate the systems that serve our enterprise carrier partners across the entire lifecycle of a life insurance policy, our consumers, and our employees. Within Bestow Engineering, our major functional teams are product engineering, infrastructure engineering, IT, data and analytics, and technical program management. Engineering partners closely with Product Management, Experience Design, and Delivery Management to define and prioritize the roadmap and to hold our commitments to carrier partners and to the business.

Our primary technologies are a microservices architecture in Golang, Python, and TypeScript on PostgreSQL, integrated over gRPC, REST, and asynchronous messaging, with event sourcing in our configuration and domain layers. We deploy and operate on Kubernetes in Google Cloud Platform.

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

WHO YOU ARE

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.

• 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.

• 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.

WHAT YOU'LL DO

Strategic Technical Leadership

• 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.

Delivery and Operational Excellence

• 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.

Team Leadership and Development

• 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.

Agentic Engineering Leadership

• 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.

The ideal candidate is a technical, inspiring leader who can hold two things at once: a partner implementation that has to ship on a contractual date, and a platform that has to get easier to configure every quarter. You are as comfortable in an architecture review as in a calibration session, and your teams get better because you lead them.