Director of Engineering — Insurance Platform & AI Delivery (Remote)

Bestow; Dallas (TX); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Equity

Remote-friendly

Flexible PTO

Medical, dental, vision insurance

Lifestyle stipend

Dallas office access

Job summary

Bestow is seeking a Director of Engineering for Insurance Product Configuration & Enrollment Platform Core. You will own technical outcomes across multiple teams, drive the architectural strategy, and partner with product and compliance to deliver scalable, compliant solutions.

You will manage 2–3 Engineering Managers and 20–30 engineers, champion agentic engineering, and lead initiatives that cross team boundaries while maintaining delivery dates and platform safety.

Qualifications

• Bachelor's degree or equivalent experience.
• 8+ years of professional software development experience.
• 5+ years of progressive engineering management experience, including managing managers (2–3 EMs, ~20–30 engineers).
• Experience designing, building, and operating distributed systems and microservices at scale.
• Strong backend experience with Golang and/or Python.

Responsibilities

• Define and drive the technical vision for Core platform aligned with Bestow's strategy.
• Lead cross-team initiatives and manage multiple teams and partners.
• Oversee architecture, delivery, and incident posture for scalable systems.
• Partner with product, delivery, underwriting, and compliance to surface requirements.
• Build a culture of technical excellence, testing, and data-driven decisions.
• Mentor engineers and engineering managers to grow leadership depth.

Skills

Distributed systems

Golang/Python

Engineering management

PostgreSQL

API design (gRPC/REST)

Cloud & Kubernetes

Cross-team leadership

Agentic engineering

Education

Bachelor's degree or equivalent

Tools

Golang

Python

PostgreSQL

Kubernetes

Google Cloud Platform

Job description

Bestow is seeking a Director of Engineering for Insurance Product Configuration & Enrollment Platform Core. You will own technical outcomes across multiple teams, drive the architectural strategy, and partner with product and compliance to deliver scalable, compliant solutions.

You will manage 2–3 Engineering Managers and 20–30 engineers, champion agentic engineering, and lead initiatives that cross team boundaries while maintaining delivery dates and platform safety.