Full-Time

Director of Talent Acquisition

Kalepa

Kalepa

51-200 employees

AI-powered underwriting decision support platform

Compensation Overview

$170k - $260k/yr

+ Equity

Remote in USA

Remote

Remote in US; prefers candidates in Eastern or Central Time zones.

Category
People & HR (1)
Required Skills
Data Analysis

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Requirements
  • 8+ years of recruiting / talent acquisition experience, with a proven track record of attracting and hiring A+ players across several functions at high-growth companies
  • 2+ years of people management experience, including building, coaching, and scaling in-house recruiting teams
  • Owned hiring outcomes at high-growth companies and know what it takes to scale hiring in a fast-paced, high-standards environment
  • Analytical and data-driven — you use recruiting metrics to diagnose problems, inform strategy, and continuously raise the bar
  • You lean heavily into building with AI, leveraging next generation tooling to multiply what talent and people can do
  • You are analytical and data-driven — you use recruiting metrics to diagnose problems, inform strategy, and continuously raise the bar
  • You are deeply aligned with Kalepa's culture and are excited to evangelize it with candidates and build a team that embodies it
  • You love to hustle: finding ways to get things done, destroying obstacles, and never taking no for an answer. “It can’t be done” is not in your vocabulary.
Responsibilities
  • Own and shape Kalepa’s talent acquisition strategy end-to-end, translating business goals into hiring plans across all functions globally - including Engineering, Product, GTM, Operations, and any other functional areas.
  • Design and own the recruiting operating model: from intake and sourcing through assessment, offer strategy, and close — ensuring consistency, rigor, and a best-in-class candidate experience at every stage.
  • Track and report on key recruiting metrics to drive continuous improvement and inform recruiting strategy and operations. Consistently make use of data to experiment with novel approaches and optimize Kalepa’s recruiting practices.
  • Lead and directly own searches across a variety of functions and levels, ensuring key roles are filled in a timely manner with A+ talent.
  • Own and evolve Kalepa employer brand to position us as the employer of choice for top talent.
  • Serve as a trusted advisor to executives and hiring managers, proactively surfacing opportunities and making data-driven recommendations.
  • Build, lead, and develop the recruiting team — setting performance standards, providing ongoing coaching, and creating a high-accountability, high-support culture.
Desired Qualifications
  • Experience using AI and next-generation recruiting tools to enhance talent acquisition
  • Track record of hiring at high-growth companies with ambitious scale and growth expectations

Kalepa provides an AI-powered decision support platform called Copilot for commercial insurance underwriters. It combines artificial and human intelligence to identify true hazards and exposures in businesses, helping underwriters make more accurate risk assessments and pricing. The platform is offered as a software-as-a-service (SaaS) to specialty carriers and other commercial insurers, enabling them to write new and renewal business more efficiently. Copilot works by blending data-driven insights with expert review to guide underwriting decisions, reducing time to quote and improving binding rates. Kalepa differentiates itself by integrating AI with human judgment to focus on real-world hazards and exposures, delivering measurable improvements in underwriting speed and accuracy. The company’s goal is to help insurance carriers reduce anticipated losses and operate more efficiently, ultimately increasing profitability through better risk selection and pricing.

Company Size

51-200

Company Stage

Series A

Total Funding

$14M

Headquarters

New York City, New York

Founded

2018

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Simplify Jobs

Simplify's Take

What believers are saying

  • Kalepa raised $14 million on January 29, 2026, extending runway.
  • April 2026 Audrey Howell joined from Palantir, strengthening product execution.
  • July 2026 careers page listed 27 open roles, signaling aggressive hiring.

What critics are saying

  • Kalepa depends on carrier renewals; one failed James River-style rollout hurts revenue quickly.
  • The MGA writes excess casualty on Everspan paper, exposing Kalepa to underwriting losses.
  • Insurers can build rival AI triage internally; Copilot's moat erodes within 12-24 months.

What makes Kalepa unique

  • Copilot automates underwriting triage, sanctions, and risk analysis across carrier workflows.
  • February 2026 James River and Merchants adopted Kalepa, validating carrier demand.
  • Kalepa's 2026 MGA pairs AI with Everspan paper for excess casualty capacity.

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Benefits

Competitive salary

Significant equity options package

100% covered medical, 100% covered vision and dental

20 days of PTO a year.

Global team offsites

Healthy living/gym stipend.

Mobile phone bill stipend

Continuing education credits

Home office stipend

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

-1%

2 year growth

0%
FF News
Aug 9th, 2024
Merchants Insurance Group Selects Kalepa’S Copilot Underwriting Platform To Power Underwriting Excellence

Merchants Insurance Group, a leading mutual insurance company based in Buffalo, NY, has chosen Kalepa‘s Copilot underwriting platform to elevate its commercial underwriting capabilities. This strategic partnership underscores Kalepa’s continued rapid growth and Merchants’ long-standing commitment to underwriting excellence.Charles Makey, President and CEO of Merchants Insurance Group, expressed enthusiasm about the collaboration, stating, “As we embark on our next century of serving policyholders, it’s imperative that we invest in cutting-edge solutions like Copilot to navigate evolving risks and market dynamics effectively. Copilot’s underwriting capabilities align with our commitment to providing tailored coverage and exceptional service to our agents, our policyholders, and our communities.”Joe Meyer, Senior Vice President of Underwriting, Product Management, and Corporate Programs at Merchants Insurance Group, highlighted ways that Copilot drives value from day one, saying, “Thanks to Copilot, we can streamline our underwriting processes immediately, and our underwriters can make even better risk decisions with greater confidence. With Copilot managing our triage process, our underwriters know exactly which submissions to prioritize and can focus their time on the risks most likely to bind profitably.”“We had heard fantastic feedback about Copilot from one of our program partners, so we knew we had to explore adopting it ourselves,” said Paul Musialowski, Director of Corporate Programs at Merchants Insurance Group. “Copilot doesn’t just scratch the surface; it dives deep into every risk, uncovering exposures and providing recommendations with full transparency and clear evidence. With Copilot, we have confidence that we’re equipped with the information we need to make informed decisions and underwrite with precision.”“We are excited to partner with Merchants Insurance Group to power their ambitions for many years to come,” said Paul Monasterio, CEO of Kalepa, “Mutual insurance companies like Merchants play a vital role in our industry, and we are proud that Copilot is the underwriting platform of choice for mutual insurers everywhere

Coverager
Jul 11th, 2022
Kalepa Forms New Mga

Kalepa, a NY-based insurance startup providing an AI-powered decision support platform for commercial insurance underwriters, has formed a new MGA. Kalepa Insurance Services, which is led by Connie Germano, will focus on small and midmarket policyholders, with policies distributed through wholesale broker partnerships. The MGA will underwrite excess casualty risks using Everspan paper, a susbsidiary of Ambac Financial Group

PR Newswire
Jul 11th, 2022
Kalepa Launches Potent Combination Of Ai And Expert Underwriting To...

Kalepa Corporation is pleased to announce the launch of Kalepa Insurance Services (KIS), an insurance offering with capacity through a program partnership with specialty insurer Everspan Group, Rated “A-” by AM Best. With the program, KIS combines the power and speed of Kalepa's proprietary AI-powered Copilot software with deep underwriting expertise to offer insurance solutions in a marketplace in need of capacity. The excess casualty program at KIS, which is writing business effective immediately, focuses on small and mid-market insureds, with policies distributed through exclusive wholesale broker partnerships. A variety of industries are in appetite