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:
Base Salary: $170K - $190K*
Year 1 OTE: $340K - $380K (uncapped commission/upside), guaranteed attainment for first two quarters of Year 1
Location Preference: This role may require up to ~50% travel depending on your location. You will be expected to spend several days per week meeting with clients and prospects in-person. There is a preference for Tri-state area or Chicago, but open to other geographies in CST or EST with access to a major airport.
Kalepa is looking for an exceptional Strategic Accounts Director with 10+ years of enterprise sales experience to help spearhead commercial growth and secure new relationships with leading US insurers. We are a VC-backed, remote-friendly startup delivering software to transform and disrupt commercial insurance. Our HQ is located in New York City.
In this sales role, you will focus on a set of named, high-value, tier 1 enterprise accounts. You will own a mix of prospects (primary focus) and cross-sell opportunities at existing accounts. Within these accounts, you will be expected to identify key influencers and stakeholders, develop new relationships and nurture existing ones, turn them into sales opportunities, and ultimately deliver large commercial agreements.
The Strategic Accounts Director will be working closely with company leadership and serve as a trusted thought partner to the prospects/clients they serve. You'll be expected to think strategically and continuously devise and execute on novel and thoughtful approaches to generate new opportunities and expand Kalepa's revenue from your set of named accounts. You will partner closely with Kalepa's Client Success team to ensure engagements are set up to deliver significant commercial impact and ROI for our clients and to evangelize Kalepa within client organizations.
About you:
- You have 10+ years of enterprise SaaS Sales experience - driving new logo sales with top tier enterprise organizations and expanding existing relationships
- Exceptional, demonstrated, ability to close and grow large enterprise SaaS contracts
- You are able to quickly develop master-level knowledge of the industry and become a thought partners to your clients, prospects, and Kalepa’s leadership
- You have experience at an early-stage startup during hypergrowth
- You can independently develop and execute sales plans to exceed Kalepa’s targets, including prospecting at the senior executive level at enterprise organizations, including publicly traded companies
- Strong verbal and written communication skills; ability to engage effectively with senior executives.
- You love to hustle: finding ways to get things done, destroying obstacles, and never taking no for an answer. The words “it can’t be done” don’t exist in your vocabulary.
- 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.
- You will be expected to spend several days per week meeting with clients and prospects in-person within your geography (Tri-state area or Midwest if based in Chicago)
- You are an excellent listener. You are perceptive to clients’ strategic priorities and business considerations. You serve as a trusted thought partner and always look for ways to enable clients further with our solution.
- You value open, frank, and respectful communication.
What you’ll get:
- Competitive salary (based on experience level)*.
- Very aggressive bonus structure, designed to reward exceptional performance.
- Significant equity options package.
- 401(k) plan with employer contribution (regardless of employee contribution)
- Work with an ambitious, smart, global, and fun team to transform a $1T global industry.
- Ground floor opportunity – very early member of Kalepa’s sales team
- Excellent benefits: 100% covered medical, 100% covered vision and dental, very generous PTO, and others.
- Global team off-sites (2021 - Playa del Carmen, 2022 - Rome, 2023 - Buenos Aires, 2024 - Lisbon, 2025 - Cartagena)
*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.
