Director of Engineering

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. 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.

As Director of Engineering, you will lead two closely coupled groups:

• Implementation Platform Configuration (IPC) owns how a carrier's products come to life on our platform.

• Enrollment Platform Core owns the workflow that keeps enrollment safe to change while multiple partner implementations are in flight.

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).

WHAT YOU'LL DO

Bestow is looking for a Director of Engineering to contribute in the following ways:

• Set technical direction. Define and drive the technical vision for Implementation Platform Configuration and Enrollment Platform Core, and make sure it ladders up to Bestow's platform strategy. Provide architectural oversight across the configuration layer, the enrollment workflow engine, and the event-sourced domain services, keeping them scalable, reliable, secure, and performant.

• Push repeatability over bespoke work. Make each new carrier implementation cost less and ship faster than the last by favoring configuration-driven patterns over hand-built per-partner solutions.

• Lead beyond your reporting line. Own initiatives whose success depends on teams that do not report to you. Own the interfaces between your teams and the ones you depend on, and resolve ownership ambiguity before it becomes an incident or a slipped date.

• Own delivery commitments. Hold your teams' commitments to carrier partners, including UAT handoff dates, and represent 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 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.

• Build a testing strategy that scales. Automated coverage, human-readable outcomes for underwriting and compliance reviewers, and repeatable regression runs in place of thousand-case manual test efforts.

• Grow the leadership bench. Lead, mentor, and grow a group of Engineering Managers. Run performance management with rigor: career ladder expectations, scorecards, calibration, direct feedback, and personalized growth plans. Maintain bench depth so a single departure does not put a partner commitment at risk.

• Own hiring for your organization. Act as hiring manager for your open requisitions, own the funnel with recruiting, and raise the bar with every hire. Manage contractor and vendor partners to the same expectations, calibration, and quality bar as our full-time engineers.

• Direct AI adoption personally. Set the strategy for where AI changes how we build rather than delegating it. Drive adoption of AI development tooling and AI-first delivery practices, establish standards for AI-generated code that reduce technical debt instead of accelerating it, and coach engineers and managers against the AI competencies in our career ladders.

• Represent Bestow externally. Speak credibly with carrier partners, vendors, and other technology companies, including in technical due diligence and vendor negotiations.

WHO YOU ARE

• Experienced as a manager of managers. Bachelor's degree or equivalent experience, 8+ years of professional software development experience , and 5+ years of progressive engineering management experience including managing managers. You will lead 2 to 3 Engineering Managers and roughly 20 to 30 engineers .

• Deep in distributed systems. Proven ability to design, build, and operate microservices architectures at scale, including event-driven and event-sourced designs.

• Fluent in our stack. Golang and/or Python backend services, API design over gRPC and REST , asynchronous messaging patterns, and extensive PostgreSQL experience covering schema design, data modeling, and query performance. Cloud platform experience, with a preference for Google Cloud Platform and Kubernetes .

• An advocate for agentic engineering. You have transformed at least one team to fully embrace agentic engineering.

• Credible across 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.

• Able to go deep when it matters. You can contribute changes to your teams' codebases and engage credibly in architectural decisions at any time.

• Serious about testing. An advocate for automated testing and test-driven development, with real opinions on how to test configuration and rules at scale.

• Organized under competing priorities. You define and track key metrics, drive accountability across teams, and consistently meet committed dates and SLAs across multiple teams and partner commitments at once.

• A builder of teams. Proven ability to attract, hire, mentor, and retain engineering talent, including developing senior engineers and early-career managers.

• A clear communicator. You can explain a complex system and its trade-offs to an executive, a carrier partner, and an engineer in the same day.

• Desirable, not required. Life insurance, annuities, or another regulated-industry background is a strong plus, as is delivering implementations for enterprise or carrier partners under contractual dates.