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Technical Support Engineer

May 12, 2026

<div class="content-intro"><h2>About Kalepa:</h2> 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 Facebook, Palantir, Google, Amazon, McKinsey, Mastercard, and Uber. <h2>Our Values (This is important):</h2> Many organizations have a dusty list of corporate values that no one ever follows. Kalepa is not one of those companies. Our values are designed to unlock the potential of our employees. Success at Kalepa is bred from five core principles: <ul> <li data-start="171" data-end="418">Hustle and Determination - We hire people who take full ownership of their craft and relentlessly pursue excellence with speed and determination. We choose the hard problems and do not give up. This is the foundation of how we work and how we win.</li> <li data-start="420" data-end="705">Deliver Customer Impact - We're obsessed with customer impact. Every feature, every line of code, every decision is measured against one question: does this help insurers make better decisions? If it doesn't drive speed, accuracy, or profitability for our customers, we don't build it.</li> <li data-start="707" data-end="924">Meritocracy - We're building something exceptional, and that requires exceptional people and ideas. We have a high bar but we reward excellence with rapid growth. If you're the best at what you do, you'll thrive here.</li> <li data-start="926" data-end="1136">Transparency - We value honest, transparent communication over politics. We challenge ideas, not people. We say what needs to be said, even when it's hard. This is how we solve problems fast and find the truth.</li> <li data-start="1138" data-end="1362">Experiment Relentlessly - Many of the problems we face have never been solved before. We tackle them by testing quickly, measuring rigorously, and iterating until we find the path forward. Speed of learning is our advantage.</li> </ul> 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). 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. </div><h2>About the role: </h2> 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. <h2>What you'll do: </h2> Technical Investigation & Resolution <ul> <li>Investigate reported issues end to end within Kalepa’s AI underwriting platform. Coordinate technical resolution end-to-end.</li> <li>Distinguish working-as-expected behavior from genuine bugs, configuration issues, user education gaps, and feature requests.</li> <li>Manage your own queue and hit response and resolution targets consistently.</li> </ul> Client Communication <ul> <li>Draft responses to Kalepa’s clients that are clear, accurate, and resolve the issue without unnecessary back and forth.</li> <li>Maintain professional, consistent communication across all client touchpoints.</li> </ul> Engineering & Cross-Functional Coordination <ul> <li>File Jira tickets with full diagnostic context when issues are confirmed bugs, so Engineering has what they need to resolve quickly.</li> <li>Identify patterns across tickets and surface them to Client Success and Product as themes worth addressing structurally.</li> </ul> Product & Subject Matter Expertise <ul> <li>Become an expert user of Kalepa, with deep familiarity across workflows, edge cases, and product behavior. Build and maintain per-client implementation knowledge. </li> </ul> <h2>About you:</h2> <ul> <li>Experience at a high-growth tech startup.</li> <li>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.</li> <li>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.</li> <li>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.</li> <li>You are operationally disciplined. You manage your own queue, hit response targets consistently, and do not let things age.</li> <li>You are metrics-driven, with a strong ability to combine quantitative and qualitative insights.</li> <li>You value open, direct, and respectful communication.</li> <li>You enjoy being part of a collaborative, thoughtful, and purpose-driven environment.</li> <li>Experience supporting complex data-heavy SaaS products</li> </ul> <h2>As a plus:</h2> <ul> <li>Insurtech or Fintech product experience.</li> </ul> <h2>What you’ll get</h2> <ul> <li style="font-weight: 400;">Competitive salary (based on experience level).</li> <li style="font-weight: 400;">Significant equity options package.</li> <li style="font-weight: 400;">401(k) plan with employer match (regardless of employee contribution)</li> <li style="font-weight: 400;">Excellent benefits: 100% covered medical, 100% covered vision and dental for individuals and families, and others</li> <li style="font-weight: 400;">Work with an ambitious, smart, global, and fun team to transform a $1T global industry.</li> <li style="font-weight: 400;">20 days of PTO a year</li> <li style="font-weight: 400;">Global team offsites (2021 - Playa del Carmen, 2022 - Rome, 2023 - Buenos Aires, 2024 - Lisbon, 2025 - Cartagena)</li> <li style="font-weight: 400;">Healthy living/gym stipend. Mobile phone bill stipend.</li> <li style="font-weight: 400;">Continuing education credits.</li> </ul> *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.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...