Technical Support Engineer

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: $85K - $135K USD*

Location: USA (Remote)

Kalepa is looking for an exceptional Technical Support Engineer with 3-5 years of experience in B2B SaaS technical support, customer-facing engineering, or a similar customer-facing technical role to be a critical member of our Support organization. This role is designed to own the technical investigation and resolution of issues across Kalepa's AI platform for insurance.

You'll be the connective tissue between our customers and our development teams, triaging and investigating complex technical issues, driving resolutions, and building the systems and processes that make our support function world-class. You'll work directly with large-scale enterprise clients who rely on Kalepa's platform to make critical decisions, so your ability to earn trust, communicate clearly under pressure, and go deep on technical problems is critical.

What you'll do:

Technical Investigation & Resolution

• Investigate reported issues end to end within Kalepa’s AI underwriting platform. Coordinate technical resolution end-to-end.
• Distinguish working-as-expected behavior from genuine bugs, configuration issues, user education gaps, and feature requests.
• Manage your own queue and hit response and resolution targets consistently.

Client Communication

• Draft responses to Kalepa’s clients that are clear, accurate, and resolve the issue without unnecessary back and forth.
• Maintain professional, consistent communication across all client touchpoints.

Engineering & Cross-Functional Coordination

• File Jira tickets with full diagnostic context when issues are confirmed bugs, so Engineering has what they need to resolve quickly.
• Identify patterns across tickets and surface them to Client Success and Product as themes worth addressing structurally.

Product & Subject Matter Expertise

• Become an expert user of Kalepa, with deep familiarity across workflows, edge cases, and product behavior. Build and maintain per-client implementation knowledge.

About you:

• Experience at a high-growth tech startup.
• You have 3-5 years of experience in a Technical Support Engineer, Senior Technical Solutions Specialist, or similar customer-facing technical role at a B2B SaaS company.
• You communicate clearly in writing. You can explain technical issues to non-technical audiences and write responses that hold up under scrutiny from sophisticated users.
• You are comfortable operating in ambiguity. Many of the issues you will own do not have a documented answer, and the right resolution requires synthesizing product behavior, client context, and operational judgment.
• You are operationally disciplined. You manage your own queue, hit response targets consistently, and do not let things age.
• You are metrics-driven, with a strong ability to combine quantitative and qualitative insights.
• You value open, direct, and respectful communication.
• You enjoy being part of a collaborative, thoughtful, and purpose-driven environment.
• Experience supporting complex data-heavy SaaS products

As a plus:

• Insurtech or Fintech product experience.

What you’ll get

• Competitive salary (based on experience level).
• Significant equity options package.
• 401(k) plan with employer match (regardless of employee contribution)
• Excellent benefits: 100% covered medical, 100% covered vision and dental for individuals and families, and others
• Work with an ambitious, smart, global, and fun team to transform a $1T global industry.
• 20 days of PTO a year
• Global team offsites (2021 - Playa del Carmen, 2022 - Rome, 2023 - Buenos Aires, 2024 - Lisbon, 2025 - Cartagena)
• Healthy living/gym stipend. Mobile phone bill stipend.
• Continuing education credits.

*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.