Account Executive (AI Insurance Platform) - Remote Eligible

Account Executive

Our client is a fast-growing innovator in insurance technology, offering a specific AI platform designed for commercial insurance carriers, MGAs, and brokers managing complex, high-volume workflows. Backed by leading investors - including Y Combinator - they partner with industry leaders handling billions in premiums annually. Their AI-powered workspace automates the most repetitive, error-prone insurance operations, from underwriting and claims to policy reviews and compliance. By mastering unstructured data and integrating across disjointed systems, they help insurance teams achieve new standards in speed, accuracy, and operational resilience.

The Mission

Our client's mission is to revolutionize insurance operations by leveraging advanced AI to automate underwriting, claim management, compliance, and related tasks. They empower insurers and brokers to achieve higher efficiency, compliance, and decision-making speed, supporting industry leaders in navigating an increasingly regulated landscape.

The Opportunity

As an Account Executive, you will take ownership of outbound enterprise sales, working directly with founders to bring a next-generation AI platform to insurance decision-makers. You'll prospect, run live demos for leaders at large carriers and brokers, and close multi-threaded, complex deals that solve real operational and compliance challenges. This is a high-impact, hands-on role ideal for entrepreneurial sellers who want to shape the sales process and see the results of their work drive real change.

What You'll Do

1. Own full outbound sales cycle: from prospecting to closing six-figure enterprise contracts
2. Run 20–25 qualified product demos per week, converting into multi-threaded opportunities
3. Build and manage a pipeline with emphasis on outbound motion and enterprise accounts
4. Collaborate with founders and leadership to optimize GTM strategy and playbook
5. Accurately forecast, manage deal velocity, and drive expansion opportunities post-initial land
6. Represent product value clearly, running polished, persuasive demos for senior insurance buyers

What You Bring

• 3+ years quota-carrying B2B SaaS/enterprise sales experience
• Proven track record of exceeding quotas in outbound-driven sales environments
• Strong demo and presentation skills (customer-facing proficiency is critical)
• Experience working in early-stage, high-growth startups
• Familiarity selling into regulated industries (insurance, finance, healthcare)
• Bonus: Background in insurance, financial services, or consulting (e.g., Oliver Wyman, Manulife)
• Bonus: Competitive, resilient, and disciplined personality; athletic or performance-driven backgrounds

Key Success Drivers

• Works well independently and adapts quickly to new situations
• Owns results in a fast-moving, high-growth team
• Builds trust with clear, honest communication
• Collaborates easily with sales, product, and engineering
• Likes to create structure and scalable processes from scratch

Why Join?

• Competitive OTE of $200,000-400,000 (50/50 split) with uncapped commissions
• Equity (0.05%–0.25%)
• H-1B, O-1, OPT visa sponsorship available
• Direct work with a YC-backed founding team
• Lunch provided in-office; vibrant, positive team culture
• Ground-floor opportunity to shape the GTM motion and playbook at a category-defining InsurTech

Interviewing Process

• HR screening
• Level 1: Interview with CEO
• Level 2: Mock customer call with an Account Executive
• Level 3: On-site working session (product experience, process building, strategy discussion)
• Reference and background checks upon successful completion of interviews
• Job offer extended to the selected candidate

We are proud to be an equal opportunity workplace and are committed to equal employment opportunity regardless of race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity, or expression, sexual orientation, or any other characteristic protected by applicable federal, state or local law.