Director of Engineering - Kalepa for Underwriting

Role overview Lead the engineering organization responsible for software that supports underwriting workflows and coordinates AI-assisted decisions. Reporting to the CTO, you will set technical direction, grow the team, and connect product strategy to dependable delivery for customers in a complex insurance environment.

Responsibilities - Hire, develop, and retain engineers while building the managers and technical leads needed as the team grows. - Set the platform architecture and technical roadmap, keeping engineering priorities aligned with business objectives. - Establish engineering standards, operating practices, and cross-functional routines that support high-quality, predictable delivery. - Work with executive, product, and go-to-market leaders to turn product goals into technical plans and measurable customer outcomes. - Use delivery, quality, reliability, and cost measures to guide operational improvements. - Explore ways to incorporate AI agents into software development and product workflows while maintaining quality and reliability. - Make and own tradeoffs among delivery speed, scope, and software quality.

Requirements - At least 10 years of relevant software engineering experience, including 3 or more years in full-time engineering management. - Strong full-stack engineering background and deep knowledge of architecture, system design, distributed systems, and scalable infrastructure. - Record of leading complex, large-scale engineering initiatives and aligning technical strategy with organizational goals. - Experience recruiting strong engineers and developing high-performing teams; experience managing managers is relevant. - Ability to make practical delivery tradeoffs in a fast-growing organization. - Experience using metrics and sound engineering practices to improve operational performance. - Experience scaling platforms using serverless technologies, asynchronous workflows, and modern cloud environments.

Nice to have - Experience in insurance, financial services, or another data-intensive regulated industry. - Production experience with large language model or agent-based systems. - Familiarity with Python, React, PostgreSQL, and AWS. - Experience leading distributed teams across time zones or scaling an engineering organization through rapid growth.

Benefits and work setup - Remote team with regional meetups and global offsites. - Equity options, 20 days of annual paid time off, and stipends for fitness, mobile service, and continuing education. - For US employees, medical, vision, and dental coverage for individuals and families, plus a 401(k) plan with employer contributions.