Director of Engineering - Kalepa for Underwriting
Kalepa · Canada · CA$260,000–CA$350,000 (stated in the posting)
About Kalepa:
Insurance is a $7T global industry built on professional labor: underwriting, claims, pricing, operations, and distribution. Kalepa is building AI that can perform that work.
We create professional-grade AI systems for insurers: software that can read, reason, decide, and act inside real workflows and operate over long-time horizons. Kalepa begins by augmenting professionals with the tools to succeed at their jobs. That earns us the right to learn from real decisions, capture decision traces, and automate what can be automated successfully over time.
Our products are already in production with leading insurers, driving measurable outcomes and expanding across functions. The opportunity is far broader than any single workflow: to build the AI operating system for decision-making across insurance. For people who want to work on AI that matters, in a sector where correctness, trust, and real-world impact count, Kalepa is just getting started.
Kalepa is backed by leading investors such as IA Ventures and Inspired Capital, and our team brings experience from Meta, Palantir, Block, Affirm, Google, Amazon, McKinsey, Mastercard, and Uber.
Our Values (This is important):
Our culture is shaped by everyday decisions. Our values help us make them thoughtfully and consistently, especially when tradeoffs are difficult. We learn from mistakes so our good decisions outweigh our bad ones and their benefits compound over time.
- Excellence - We take pride in our craft and expect excellent outcomes in everything we do. We set high standards, verify our work, and own the result. We make deliberate tradeoffs, including rethinking an approach, redoing work, or investing more time.
- Pursuit of the Truth - We seek the truth, even when it is uncomfortable. We question assumptions, give candid feedback, and change our minds when evidence warrants it. We work with customers to understand their challenges and what solving them requires.
- Ensuring Customer Success - We take responsibility for delivering results that matter to our customers. We measure success through improvements in their growth, profitability, and efficiency. We challenge our approach and customers’ requests when necessary, remaining accountable for the outcome.
- First Principles Thinking - We reason from a problem’s underlying facts, objectives, and constraints. We distinguish what is necessary from what is familiar and question assumptions that limit possible solutions. We test our reasoning against reality and address root causes with approaches that scale without unnecessary complexity.
In addition to our NY office, we have remote employees speaking 10+ languages across the globe. But we invest in bringing our people together both for regional meetups and global offsites (2021 - Playa Del Carmen | 2022 - Rome | 2023 - Buenos Aires | 2024 - Lisbon | 2025 - Cartagena | 2026 - Tbilisi).
Kalepa’s culture isn’t for everyone, and that’s ok. But for the people who are a fit, they can’t imagine working elsewhere.
About the role:
Kalepa is looking for an exceptional Director of Engineering to lead and grow the Kalepa for Underwriting team. We are looking for a deeply technical leader with extensive experience in full-stack engineering who is excited to partner closely with the executive team and cross-functional leaders to shape the future of Kalepa’s product. You will be responsible for defining the architectural roadmap, setting strategy, driving engineering operational excellence, and cultivating a high-performance, results-driven culture that consistently delivers exceptional value to Kalepa’s clients.
You will establish the frameworks, engineering standards, and cross-functional cadences to power Kalepa’s cutting-edge platform which augments human underwriters and orchestrates AI underwriters to deliver rapid and profitable growth to the world’s largest insurers. You will bridge the gap between product vision and technical execution, ensuring our technology investments directly drive business impact and long-term business growth. This role is ideal for someone who cares deeply about quality, is actively rethinking the way that software is built and shipped, and wants to shape the way Kalepa impacts the most critical decisions made at the largest insurance companies.
Salary range
We differentiate our North America salary ranges using two geographical zones:
Zone 1 (New York and San Francisco) - $260,000 to $350,000*
Zone 2 (all other locations in the US and Canada) - $230,000 to $350,000*
Location
We are primarily a remote company with employees across the US, Canada, and Europe. Our HQ is in New York city.
About the team
Kalepa for Underwriting delivers superior underwriting outcomes by rendering best-in-class underwriting decisions autonomously, or presenting insights and recommendations that enable a human underwriter to grow premium profitably.
What you’ll do:
- Lead and grow the Kalepa for Underwriting engineering team: hire, develop, and retain top engineers, and build the managers and tech leads beneath you as the team scales.
- Define the architectural roadmap and technical strategy for the platform that augments human underwriters and orchestrates AI underwriters, and keep it aligned with Kalepa’s company objectives.
- Establish the frameworks, engineering standards, and cross-functional cadences that let the team ship high-quality software quickly and predictably.
- Partner with the executive team, product, and go-to-market leaders to bridge product vision and technical execution, ensuring technology investments drive measurable business impact.
- Drive operational excellence through metrics-driven decision-making across delivery, quality, reliability, and cost.
- Rethink how software is built and shipped at Kalepa, including how the team deploys AI agents alongside engineers while maintaining quality and reliability.
- Own the tradeoffs between speed, quality, and scope within the constraints of a fast-growing company, and be accountable for the outcomes.
- Cultivate a high-performance, results-driven culture that consistently delivers exceptional value to Kalepa’s clients.
About you:
- You have 10+ years of relevant software engineering experience with at least 3 years of full-time engineering people management experience, ideally including experience managing managers and scaling organizations.
- You are known for rethinking the way that engineering is done and feel right at home managing both human and AI agents, while ensuring quality and reliability.
- You have a proven track record of driving complex, large-scale engineering initiatives and aligning technical strategy with broader company objectives.
- You are an excellent recruiter of top-tier engineering talent and somebody who exceptional software engineers want to work with.
- You have the ability to make the tradeoffs required to ship high-quality code while working within the constraints of a fast-growing company.
- You drive operational excellence by championing metrics-driven decision-making and implementing robust engineering practices.
- You thrive on experimentation: you're comfortable testing ideas, measuring results, and iterating quickly on problems no one has solved before.
- You have deep architectural expertise and a strong foundation in system design, distributed systems, and scalable infrastructure.
- You have experience overseeing and scaling platforms utilizing serverless technologies (Lambda, EC2), asynchronous workflows, and modern cloud environments.
Bonus points for:
- 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.
What you’ll get:
- Competitive salary (based on experience level)*.
- Significant equity options package.
- 20 days of PTO a year.
- Global team offsites (2024 - Lisbon, 2025 - Cartagena, 2026 - Tbilisi).
- Healthy living/gym stipend.
- Mobile phone bill stipend.
- Continuing education credits.
For US employees only:
- 100% covered medical, 100% covered vision and dental for individuals and families.
- 401(k) plan with employer contribution (regardless of employee contribution)
*The salary range listed is an estimate and will vary based on a variety of factors. Final compensation will be determined during the offer stage based on relevant experience, performance during the interview process, and geographic location, and may therefore differ from the posted range.