Lead Product Designer (United States or Canada, Remote)

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:

Salary range: $150 - 220K USD*

We’re looking for a talented and versatile Lead Product Designer to join our team and help improve the new experiences of our platform. You’ll own complex, cross-cutting problems, shape what we build as well as how it looks, and raise the bar for design quality across the team. You’ll collaborate closely with our current Lead Designer, product managers, and engineers to bring polish, clarity, and structure to complex workflows. This role reports to the Head of Product.

What You’ll Do

• Lead design for the platform’s most complex, cross-cutting problems, from discovery and research through delivery and iteration.
• Turn ambiguous problems and new business areas into clear product direction, partnering with product, client success, and sales to balance user needs and business goals.
• Design data-dense workflows that help underwriters find what matters and act on it with confidence.
• Define how AI shows up in the product: how we communicate confidence, surface sources, and keep underwriters in control of decisions.
• Establish scalable patterns so the platform can grow across new lines of business without fragmenting the experience.
• Use AI and rapid prototyping tools to move quickly from idea to validated concept.
• Raise the design bar across the team through critique, mentorship, and shared standards.

About You

• 7+ years of experience designing digital products for B2B, data-rich, or productivity tool companies. 
• Experience working in a rapidly scaling, ownership-mentality startup environment.
• Experience designing AI-driven tools.
• Experience taking an existing platform and helping to generalize and scale the user experience to support new and expanding workflows.
• A strong portfolio showcasing your ability to simplify complexity, design thoughtful UIs, and apply clear interaction patterns.
• Systems thinking, with experience shaping and contributing to design systems.
• Strong visual design skills and attention to detail—particularly in information hierarchy, interaction, and layout.
• Excellent communication and collaboration skills—you’re proactive, responsive, and eager to get feedback.
• Curious and adaptable—you enjoy solving ambiguous problems and growing your skills in the process.

Bonus Points For

• Experience working with MUI (Material UI) or similar design systems.
• InsurTech, FinTech, or other highly-regulated industry experience.
• A technical background or interest in how things are built.

*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.