Remote Director, Strategic Accounts

Kalepa is an award-winning AI software company transforming the trillion-dollar commercial insurance industry. Our state-of-the-art AI Copilot platform empowers underwriters to make smarter, faster, and more accurate decisions, so insurers can grow their top and bottom lines while business owners get the coverage they need.

Copilot is delivering real, tangible impact to insurers from day 1, and underwriters rave about it. . “[They] dont know if [they] could function doing daily underwriting without having it. ” and they assert that "not only is Kalepa’s technology miles ahead of other vendors, but when it came to driving real impact on our business, there [is] no competition."

Kalepa’s Copilot powers insurers of all sizes, including +$10B carriers like Arch and Munich Re, hypergrowth MGAs like Bowhead Specialty and Paragon, and small regional insurers like North Star Mutual.

At Kalepa, youll join a team of doers who are passionate about innovating and winning. We are a fast-moving group with high expectations for every person we hire and everything we build.

Join us if you want to be a crucial part of a company whose AI actually works.
Base Salary : $145K - $185K

Target Commission : $200K (uncapped)

Equity : 0.15% to 0.35%

Job Title: Director, Strategic Accounts

Strong Location Preference: Tri-state Area | Chicago

Kalepa is an award-winning AI software company transforming the trillion-dollar commercial insurance industry. Our state-of-the-art AI Copilot platform empowers underwriters to make smarter, faster, and more accurate decisions, so insurers can grow their top and bottom lines while business owners get the coverage they need.

Copilot is delivering real, tangible impact to insurers from day 1, and underwriters rave about it. “[They] dont know if [they] could function doing daily underwriting without having it,” and they assert that "not only is Kalepa’s technology miles ahead of other vendors, but when it came to driving real impact on our business, there [is] no competition."

Kalepa’s Copilot powers insurers of all sizes, including +$10B carriers like Arch and Munich Re, hypergrowth MGAs like Bowhead Specialty and Paragon, and small regional insurers like North Star Mutual.

At Kalepa, youll join a team of doers who are passionate about innovating and winning. We are a fast-moving group with high expectations for every person we hire and everything we build.

Join us if you want to be a crucial part of a company whose AI actually works.

Kalepa is looking for an exceptional Director, Strategic Accounts 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 Director, Strategic Accounts 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 Copilot 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 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.

Requirements:

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)

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, October 2024 - Lisbon)

Kalepas team members bring experience from top technology, including Facebook, Google, Amazon, Mastercard, and Uber. Kalepa is backed by IA Ventures (early investors in Datadog, Wise, Better, Digital Ocean, TheTradeDesk, Flatiron Health, Komodo Health, etc.); former Secretary of Commerce Penny Pritzker’s Inspired Capital; and leaders in financial services and technology, including Gokul Rajaram from Doordash, Coinbase, and Square, Jackie Reses from Square, Affirm, and Alibaba, and Henry Ward from Carta.