Full-Time

Strategic Accounts Director

ET/CT US

Posted on 7/25/2025

Kalepa

Kalepa

51-200 employees

AI-powered underwriting decision support platform

Compensation Overview

$175k - $190k/yr

+ Year 1 OTE + Guaranteed attainment Year 1 + Quarterly Bonus + Commission

United States

Hybrid

In-person client meetings required several days per week; location policy centers on Tri-state area or Midwest for Chicago-based candidates.

Category
Sales & Account Management (2)
,
Requirements
  • 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 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 Copilot solution.
  • You value open, frank, and respectful communication.
  • 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 will be spending several days per week meeting with clients and prospects in-person within your geography (Tri-state area or Midwest if based in Chicago)
Responsibilities
  • Win accounts that have the potential to become 8-figure per year relationships for Kalepa.
  • Develop master-level knowledge of the industry and become a thought partner to clients, prospects, and Kalepa’s leadership
  • Develop and execute sales plans to exceed targets, including prospecting at the senior executive level at enterprise organizations, including publicly traded companies
  • Engage with senior executives and clients to understand strategic priorities and enable the Copilot solution
  • Represent Kalepa in the market, build and maintain relationships with strategic accounts, forecast growth and contribute to the development of the company strategy
  • Manage the sales cycle from prospecting to closing deals and renewing existing relationships
  • Collaborate with cross-functional teams including product, marketing, and customer success to deliver solutions and close deals
  • Travel as needed to meet with clients and prospects across geography
Desired Qualifications
  • Experience selling to financial services or insurance industries
  • Experience selling AI software
  • Track record of closing multi-million dollar ARR deals
  • Knowledge of enterprise software procurement processes and familiar with procurement terms
  • MBA or advanced degree in business or a related field
  • Strong network within target enterprise accounts and relationships with key decision-makers
  • Experience working in an early-stage startup during hypergrowth (duplicated)

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

Simplify Jobs

Simplify's Take

What believers are saying

  • Merchants Insurance Group adopted Copilot to streamline underwriting triage.
  • Beyond Risk selected platform to automate intake and boost MGA growth.
  • Kalepa Insurance Services launched excess casualty MGA with Everspan.

What critics are saying

  • Shift Technology's end-to-end AI erodes hybrid Copilot model.
  • Everspan's A- downgrade halts Kalepa MGA capacity in 6-12 months.
  • Munich Re and Arch build in-house AI, terminating subscriptions.

What makes Kalepa unique

  • Copilot combines AI and human intelligence for precise commercial underwriting.
  • Platform triages submissions, prioritizing profitable risks for underwriters.
  • Trusted by Arch, Munich Re, Paragon, and Bowhead Specialty.

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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

-1%

1 year growth

-3%

2 year growth

-7%
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

Cision
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

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