Director of Engineering - Kalepa for Underwriting
About The Position
Kalepa is seeking a deeply technical Director of Engineering to lead and grow the Kalepa for Underwriting team. The role partners closely with the executive team and cross-functional leaders to shape product direction, define the architectural roadmap and technical strategy, drive engineering operational excellence, and develop a high-performance culture that delivers value to clients. The Director will establish engineering frameworks, standards, and cross-functional cadences for a platform that augments human underwriters and orchestrates AI underwriters. The role connects product vision with technical execution and ensures technology investments contribute to measurable business impact and long-term growth. It calls for a leader who cares deeply about quality, is rethinking how software is built and shipped, and wants to help shape technology used in consequential decisions at major insurance companies. Kalepa for Underwriting aims to improve underwriting outcomes by making superior underwriting decisions autonomously or by giving human underwriters insights and recommendations that support profitable premium growth. Kalepa is primarily remote, with employees across the US, Canada, and Europe, and is headquartered in New York City.
Requirements
- 10+ years of relevant software engineering experience.
- At least 3 years of full-time engineering people-management experience; experience managing managers and scaling organizations is ideal.
- A track record of leading complex, large-scale engineering initiatives and aligning technical strategy with company objectives.
- Strong recruiting ability and the ability to attract top-tier engineering talent.
- Ability to make tradeoffs that support high-quality software delivery within the constraints of a fast-growing company.
- Experience championing metrics-driven decision-making and implementing robust engineering practices.
- Comfort with experimentation, measuring results, and iterating on novel problems.
- Deep architectural expertise and a strong foundation in system design, distributed systems, and scalable infrastructure.
- Experience overseeing and scaling platforms using serverless technologies such as Lambda and EC2, asynchronous workflows, and modern cloud environments.
- Ability to rethink engineering practices and manage both human and AI agents while ensuring quality and reliability.
Nice To Haves
- 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 rapid company growth.
Responsibilities
- Lead and grow the Kalepa for Underwriting engineering team by hiring, developing, and retaining engineers, and building managers and technical leads as the team scales.
- Define the platform's architectural roadmap and technical strategy, keeping them aligned with company objectives.
- Establish frameworks, engineering standards, and cross-functional cadences that enable high-quality, predictable software delivery.
- Partner with executive, product, and go-to-market leaders to connect product vision with technical execution and ensure technology investments drive measurable business impact.
- Drive operational excellence through metrics-based decisions about delivery, quality, reliability, and cost.
- Rethink how software is built and shipped, including how AI agents are deployed alongside engineers while maintaining quality and reliability.
- Manage tradeoffs among speed, quality, and scope in a fast-growing company and remain accountable for outcomes.
- Cultivate a high-performance, results-driven culture that consistently delivers value to clients.
Benefits
- Competitive salary based on experience level.
- Significant equity options package.
- 20 days of PTO per year.
- Global team offsites.
- Healthy living/gym stipend.
- Mobile phone bill stipend.
- Continuing education credits.
- For US employees: 100% covered medical, vision, and dental insurance for individuals and families.
- For US employees: 401(k) plan with employer contribution, regardless of employee contribution.
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
