Skip to content
BestowBestow

Engineering Director

Leads multiple engineering teams responsible for insurance product configuration, enrollment workflows, and core domain services. The role requires deep distributed-systems expertise, backend development experience, strong operational leadership, and a track record of managing managers in a regulated or enterprise environment.

About the job

Responsibilities

Strategic Technical Leadership

  • Define and drive the technical vision for the Core organization, aligning it with platform strategy and business objectives.
  • Promote configuration-driven repeatability over bespoke partner implementations.
  • Provide architectural guidance across configuration layers, enrollment workflow engines, and event-sourced domain services.
  • Lead cross-team initiatives and own interfaces and dependencies across engineering teams.
  • Represent the company with carrier partners, vendors, and technology companies in technical due diligence and vendor negotiations.
  • Evaluate emerging technologies and foster technical excellence, innovation, and continuous learning.

Delivery and Operational Excellence

  • Own delivery commitments to carrier partners, including UAT handoff dates and executive status reporting.
  • Partner with Product, Delivery Management, Underwriting, and Compliance to identify requirements and dependencies early.
  • Own incident posture, including prioritization, root-cause analysis, systemic improvements, and follow-up actions.
  • Ensure service-owning teams operate their services and supporting infrastructure in partnership with platform engineering.
  • Build scalable testing strategies for rules and configuration, including automated coverage, human-readable outcomes, and repeatable regression runs.
  • Use data and metrics to guide technical decisions, system health monitoring, and engineering investment.
  • Translate business and partner roadmaps into technical strategies and staffing plans.

Team Leadership and Development

  • Lead, mentor, and grow Engineering Managers and develop the leadership bench beneath them.
  • Build and scale high-performing engineering teams.
  • Manage 2–3 Engineering Managers and approximately 20–30 engineers across multiple teams.

Requirements

  • Bachelor's degree or equivalent experience.
  • 8+ years of professional software development experience.
  • 5+ years of progressive engineering management experience, including managing managers.
  • Experience designing, building, and operating distributed systems and microservices at scale.
  • Experience with event-driven and event-sourced architectures.
  • Extensive relational database experience, particularly PostgreSQL, including schema design, data modeling, and query performance.
  • Strong experience with Golang and/or Python backend services.
  • Experience with API design using gRPC and REST, plus asynchronous messaging patterns.
  • Recent experience transforming a team to embrace agentic engineering.
  • Deep software development lifecycle expertise, including design, delivery, continuous delivery, release strategy, monitoring, and improvement.
  • Ability to reason across frontend composition, data platforms, and infrastructure and resolve cross-team issues.
  • Ability to contribute to codebases and engage in architectural decisions.
  • Experience with automated testing and test-driven development.
  • Experience with cloud platforms, preferably Google Cloud Platform and Kubernetes.
  • Ability to define metrics, drive accountability, and meet commitments and SLAs.
  • Strong organizational, communication, hiring, mentoring, and talent-retention skills.

Nice-to-Haves

  • Experience in life insurance, annuities, or another regulated industry.
  • Experience delivering enterprise or carrier-partner implementations under contractual deadlines.

Compensation and Benefits

  • Flexible remote/hybrid work.
  • Meaningful benefits, equity, and substantial growth opportunities.

Skills

Go, Python, TypeScript, Postgres, gRPC, Rest, Kubernetes, GCP, Microservices, Distributed Systems, Event Sourcing, Asynchronous Messaging, Test-Driven Development, Agentic Engineering, API Design

Motive

Motive

San Francisco, CA
Director, Developer Platform & Experience
$229k+/yrHybrid12+ YOEEngineering Management

Leads a multi-team organization responsible for AI-assisted development, cloud agentic infrastructure, developer experience, CI/CD, testing, and engineering velocity. Requires extensive software engineering and engineering leadership experience, deep infrastructure expertise, and hands-on knowledge of AI developer tooling and LLM evaluation.

Rippling

Rippling

San Francisco, CA

Director of Engineering, HRIS Core Flows
$216k+/yrOn-site8+ YOEEngineering Management

Leads a 15-person engineering organization responsible for enterprise employee lifecycle workflows and an AI-assisted HR workflow charter. The role requires multi-team leadership, strong technical and product judgment, and experience with high-stakes, global, workflow-heavy platforms.

Okta

Okta

San Francisco, CA

Senior Director, GRC
$236k+/yrOn-site10+ YOEEngineering Management

Leads Okta’s security GRC organization, overseeing enterprise cyber risk, AI governance, global compliance, audits, vendor risk, and engineering-driven remediation. The role requires 10+ years of progressive Security GRC leadership, cloud technology experience, AI governance expertise, and a bachelor’s degree or equivalent experience.

LeafLink

LeafLink

United States

Head of Engineering
$240k+/yrRemote12+ YOEEngineering Management

Leads the entire engineering organization, owning technical vision, architecture, execution standards, security, budget, and organizational scaling. The role requires extensive software engineering and engineering management experience, cloud-native architecture expertise, and a record of building high-performing teams.

Celonis

Celonis

New York, NY

Senior Director, Professional Services
$204k+/yrHybrid9+ YOEEngineering Management

Leads Celonis’s professional services strategy, delivery, commercial growth, and talent development across a sub-regional customer portfolio. The role requires extensive consulting or SaaS implementation experience, senior leadership, services sales expertise, forecasting or P&L ownership, and executive stakeholder management.