Principal Sales Engineer (USA)

Commercial insurance is a trillion-dollar industry run out of Microsoft Outlook.

Kalepa is upending this.

Our state-of-the-art AI Copilot platform empowers underwriters to make smarter, faster, and more accurate decisions. Our AI is designed to deliver real results - insurers literally see massive improvements to their top and bottom lines as soon as they implement Copilot. That’s why our clients call Copilot “truly an underwriter’s dream” and proclaim that Copilot helps them “almost double the amount of accounts they can look at in the day."

Kalepa's team members bring experience from top technology companies, including Facebook, Google, Amazon, Mastercard, and Uber. Kalepa is backed by leading VCs like IA Ventures and Inspired Capital.

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:

• Hustle & Grit - We expect everyone at Kalepa to be excellent at what they do and relentless in pursuing their craft. There are no easy days. Kalepa’s exceptional speed and determination are our biggest differentiators: this is how we win.
• Customer Focus - We will ruthlessly prioritize the work that drives our clients’ growth, profitability, and efficiency. We are not building things just because they seem cool - we are here to solve our customers’ most strategic problems.
• Meritocracy - Too many exceptional people are stifled by corporate bureaucracies. At Kalepa, those people excel - and we reward tremendous results with rapid promotions and compensation growth.
• Transparency - We are honest with each other. We don’t believe in back-office politics and keeping employees in the dark. Transparency allows us to instantly cut to the heart of the matter and figure it out together.
• Experimentation - For many of the problems we face, no company has ever solved them before. We tackle these by quickly testing, measuring, and iterating to determine the path to success.

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.

Base Salary: $150-$170KOTE: $215-243K

Location: Located in Eastern or Central time. Special preference given to Chicago, New York, and Raleigh.

Kalepa is looking for an exceptional Sales engineer with 7+ years of enterprise sales engineer experience to help accelerate Kalepa’s commercial efforts with leading insurers. You will serve as a critical technical and consultative resource throughout the sales process, working with prospective clients to show how Kalepa’s software can elevate their underwriting process and drive measurable value for the insurer.

You will partner directly with Account Executives, and be a close collaborator with Kalepa’s Product, Engineering, and Client Success teams to help bring the software to life and successfully bring new clients into the fold.

This is a unique opportunity for someone with fantastic interpersonal commercial skills, a strong technical acumen, and ability to translate the language of complex processes into comprehensible solutions. You will report to Kalepa’s Director of Sales Engineering and maintain principal responsibility for the SE efforts on your assigned accounts.

• Act as a trusted advisor during the sales cycle, guiding prospective clients through the technical and business evaluation of Kalepa’ platform
• Support and coordinate responses to RFPs, RFIs, and due diligence questionnaires
• Design and lead tailored demos and workshops, to bring the software to life in an insurer-specific context
• Travel up to 15% of the time to lead in-person sales workshops, going deep on the product, speaking to the prospect’s use case, and mapping out what a successful deployment would look like
• Scope engagements, draft Statements of Work (SOW), and set delivery timelines in collaboration with cross-functional teams
• Facilitate seamless transitions to Kalepa’s Client Success team
• Collaborate on foundational sales engineering processes, playbooks, and collateral that will support future growth in the region
• Help Kalepa win deal after deal

• 7 years of experience in financial services or financial technology, ideally with exposure to insurance, wealth management, investment platforms, or SaaS deployments. Candidates who also have experience with complex SaaS solutions that can articulate and demonstrate value over features.
• Prior experience in roles such as solutions engineering, sales engineering, client onboarding, pre-sales, product management, or technical consulting
• You love to hustle: finding ways to get things done, destroying obstacles, and never taking no for an answer.
• You are passionate, deeply motivated, and have a strong will to win. You are excited about bringing a world-class solution to clients and to helping them win in-market.
• Strong communication and presentation skills, with the ability to influence and educate stakeholders across varying levels of technical understanding
• AI-forward thinker, with a deep interest in artificial intelligence and constant emphasis on leveraging new capabilities to improve and streamline your work

• Experience in technology for regulated industries like insurance or financial services
• Strong technical foundation with the ability to discuss architecture, APIs, and integration patterns fluently
• Fluent in SQL, Excel wizardry, or Python scripting. Prompt engineering experience is a plus
• Understanding of AI, ML, and automation concepts (we can teach this!)
• A deep love for tech, data, and using both to drive better outcomes
• You have an experience at a growth-stage startup helping to scale the company during hypergrowth

• 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.