Bestow Engineering Director at Bestow leads the Insurance Product Configuration & Enrollment Platform Core team. The role manages engineering managers, leads cross-team initiatives, and owns outcomes spanning multiple teams in a regulated domain.
Responsibilities
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.
Qualification
Proven ability to designStrong advocate for agentic engineering
Required
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.
