Engineering Manager; Communications Team

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. Carriers choose us to scale and operate at unprecedented speed, powered by AI and automation.

Bestow isn't selling policies. We're building the infrastructure that helps an entire industry move faster, reach more people, and deliver on its promise.

Backed by leading investors (Goldman Sachs, Hedosophia, NEA, Valar, 8VC) and trusted by major carriers, Bestow is powered by a team that moves with precision, purpose, and heart. If you want to help reimagine a centuries-old industry with lasting impact, join us.

Bestow offers flexible remote/hybrid work, meaningful benefits, equity, and substantial growth opportunities.

Bestow uses E-Verify to confirm the employment eligibility of all newly hired employees. To learn more about E-Verify, including your rights and responsibilities, please visit E-Verify.gov.

The Engineering team is responsible for all technology for Bestow and the Bestow Platform. We serve employees, consumers, and enterprise customers. In addition to building software, we integrate and manage many third-party products used by employees and as part of the platform. Our major functional teams are product engineering, infrastructure, IT, data & analytics, and program management. Engineering works closely with product management and design to define and prioritize the product roadmap.

As an Engineering Manager for the Communications Team, you will lead a team of Backend Software Engineers responsible for Bestow's communications infrastructure, the Document Creation Service and Notification Service. You will partner with Product Managers, Compliance, Legal, and our external delivery partners to develop and support solutions that power document generation, regulatory disclosures, and multi-channel customer communications across the platform. You will also collaborate with teams across Bestow to plan and execute the product roadmap.

Our system runs on Kubernetes in Google Cloud Platform and is composed of several microservices written in Go that integrate using gRPC, REST, and async messaging patterns. You will share responsibility for operating our workloads on these platforms.

A key focus for this role will be scaling our communications infrastructure, building reliable, compliant document generation and multi-channel notification delivery (email, SMS, and physical mail) that supports policy documents, required notices, automated delivery tracking, and seamless carrier and partner integrations.

This role is open to remote candidates. #LI-Remote

This is a player/coach role with direct reports, spending approximately 20% of your time contributing production-level code.

• Remain hands-on in the code and actively participate in system design and architecture decisions

• Regularly review pull requests, providing thoughtful feedback that elevates code quality

• Partner with engineers on complex technical challenges, offering guidance without micromanaging

• Drive large initiatives from conception through delivery

• Own the document generation pipeline including templating, PDF rendering, carrier-and product-specific document configuration, and template lifecycle management

• Lead multi-channel notification delivery across email, SMS, and physical mail, including third-party provider integrations (e.g., Lob, Send Grid, Twilio), delivery status tracking, and webhook handling

• Design delivery failure handling including correct classification of provider errors (e.g., distinguishing user/4xx from system/5xx failures), retry logic, bounce/complaint management, and operational alerting

• Build compliance-driven communications infrastructure for regulatory disclosures, required notices, document verification, and end-to-end audit trails for document delivery

• Implement delivery observability including exposure of delivery failures in data feeds, idempotent retries, and custom monitoring/eventing for template processing

• Drive operational improvements including carrier template onboarding automation, reducing manual intervention, and streamlining the document-to-delivery lifecycle

• Orchestrate effective engineering ceremonies that promote collaboration and continuous improvement

• Create personalized growth plans for each team member, identifying strengths and development areas

• Provide regular, constructive feedback and create opportunities for engineers to expand their skills

• Balance technical excellence with business objectives

• Demonstrate sound judgment when making technical trade-offs

• Communicate complex technical concepts clearly to both…