Engineering Director - Bestow

About Bestow

Life insurance is one of the world's most important products. It's also one of the hardest to build, distribute, and modernize. Bestow exists to change that. Bestow is a leading vertical technology platform serving some of the largest and most innovative life insurers. Our platform unifies the fragmented, legacy value chain, enabling carriers to launch products in weeks instead of years.

About the Role

The Director of Engineering for Insurance Product Configuration & Enrollment Platform Core will be a highly technical, strategic engineering leader who is comfortable owning outcomes across teams. You understand distributed systems deeply, hold a firm line on quality in a regulated domain, and 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).

Responsibilities

Strategic Technical Leadership

• Define and drive the technical vision for your teams' core components, ensuring it aligns with Bestow's platform strategy and business objectives.
• Push configuration-driven repeatability over bespoke per-partner work so each new carrier implementation costs less and ships faster.
• Provide architectural guidance and oversight across the configuration layer, enrollment workflow engine, and event-sourced domain services.
• Lead initiatives whose success depends on cross-functional and cross-team collaboration.

Delivery and Operational Excellence

• Own your teams' delivery commitments to carrier partners, including UAT handoff dates, and represent status accurately to executive leadership.
• Head off requirements churn at the source by partnering with Product, Delivery Management, Underwriting, and Compliance.
• Own your organization's incident posture, drive urgency and priority grading, and insist on real root-cause analysis.
• Build a testing strategy that scales with the rules and configuration we ship.

Team Leadership and Development

• Lead, mentor, and grow a group of Engineering Managers, leading 2–3 managers and roughly 20–30 engineers across multiple teams.
• Build and scale high-performing teams with a strong sense of ownership, accountability, and psychological safety.
• Run performance management with rigor, establish clear career ladder expectations, and act as hiring manager for open requisitions.

Agentic Engineering Leadership

• Direct the adoption of AI-augmented development in your organization, setting strategy for AI-first delivery practices (AIDLC).
• Drive adoption of AI development tooling (Claude Code, Claude Tag, GitHub Copilot) and establish standards for AI-generated code.

Qualifications

• Bachelor's degree or equivalent experience.
• 8+ years of professional software development experience.
• 5+ years of progressive engineering management experience, including managing managers.
• 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, having recently transformed at least one team to fully embrace it.
• Deep expertise across the software development lifecycle.
• Life insurance, annuities, or other regulated-industry experience is a strong plus.