Director of Engineering - Kalepa for Underwriting

The role

The Director of Engineering will lead and grow the Kalepa for Underwriting team. You will define the architectural roadmap, set strategy, and drive engineering operational excellence to support a platform that augments human and AI underwriters.

What you will do

• Lead and grow the Kalepa for Underwriting engineering team
• Define the architectural roadmap and technical strategy
• Establish frameworks, engineering standards, and cross-functional cadences
• Partner with executive, product, and go-to-market leaders
• Drive operational excellence through metrics-driven decision-making
• Rethink how software is built and shipped
• Own tradeoffs between speed, quality, and scope
• Cultivate a high-performance, results-driven culture

Required qualifications

• 10+ years of relevant software engineering experience
• At least 3 years of full-time engineering people management experience
• Proven track record of driving complex, large-scale engineering initiatives
• Ability to make tradeoffs required to ship high-quality code in a fast-growing company
• Deep architectural expertise
• Strong foundation in system design, distributed systems, and scalable infrastructure
• Experience overseeing and scaling platforms utilizing serverless technologies (Lambda, EC2), asynchronous workflows, and modern cloud environments

Nice to have

• Experience building or scaling products for insurance, financial services, or another data-heavy regulated industry
• Hands-on experience with LLM-based or agentic systems in production
• Experience with Kalepa’s stack: Python, React, PostgreSQL, and AWS
• Experience leading distributed, multi-time-zone engineering teams
• A track record of scaling an engineering organization through a stage of rapid company growth

Benefits

• Competitive salary
• Significant equity options package
• 20 days of PTO a year
• Global team offsites
• Healthy living/gym stipend
• Mobile phone bill stipend
• Continuing education credits
• 100% covered medical, 100% covered vision and dental for individuals and families (US employees only)
• 401(k) plan with employer contribution (US employees only)

About the company

Kalepa is building AI that can perform professional labor in the insurance industry. The company creates professional-grade AI systems for insurers to read, reason, decide, and act inside real workflows.