YC - Account Executive - AI Agents - InsureTech - Hybrid

Account Executive – Insurance AI Platform

Compensation:
$250,000 - $300,000 OTE (base + variable)

Location:
In-office, San Francisco

About Our Client

Our Y-combinator client is on a mission to reinvent how insurance carriers and brokers handle customer interactions across service, claims intake, and quoting.

They build agentic voice, chat and email AI that helps Property & Casualty (P&C) and Life insurance teams turn frustrating customer experiences into instant, personalized conversations. From new quotes to renewals to First Notice of Loss (FNOL) calls, their platform automates the routine so that teams can focus on what actually matters.

They're growing incredibly fast and expanding their footprint with top carriers and brokers across the U.S. The opportunity is massive, and they're looking for a driven Account Executive to help them capture it.

This is a career-defining role for someone who wants to sell into a trillion-dollar industry at an inflection point for AI adoption.

A Day in the Life

As an Account Executive, you'll own the sales process end-to-end, from discovery to close, with some of the most innovative players in the insurance space.

Your day will include:

• Driving new business with VPs of Operations, Claims, and Sales at mid-market and enterprise insurance carriers and brokers.

• Running discovery and consultative demos that uncover inefficiencies in customer service, claims intake, and quote intake.

• Mapping complex org structures and building multi-threaded relationships with both technical and business leaders.

• Collaborating with product and engineering to communicate customer feedback and influence roadmap priorities.

• Managing a clean, high-velocity pipeline in HubSpot with precision forecasting.

• Closing deals that help insurance leaders scale service, reduce costs, and delight policyholders.

• Acting as a trusted advisor, not a vendor, guiding customers through the path from manual service to AI automation.

Who We're Looking For

You're not a script reader. You're a curious, articulate problem-solver who loves selling complex technology into traditional industries, and helping customers cross the chasm to something new.

You bring:

• 3-5 years of B2B SaaS sales experience, ideally in insurtech, fintech or AI.

• Experience selling to operations or customer service leaders at mid-market or enterprise firms.

• A strong understanding of the sales process: discovery, qualification, demo, objection handling, and close.

• Exceptional written and verbal communication skills.

• A consultative approach – you listen deeply, simplify complexity, and earn trust.

• A growth mindset – hungry to learn, iterate, and master enterprise sales.

• Grit, resilience, and the ability to navigate long cycles and multiple stakeholders.

• Proficiency in HubSpot, PowerPoint, and CRM best practices.

Bonus points for:

• Experience in insurance SaaS, contact center, or AI automation sales.

Who You Are

• You're a business athlete – competitive, coachable, and relentless.

• You thrive in ambiguity and early-stage environments.

• You bring empathy to every conversation and always fight for the customer.

• You believe in software that scales people, not replaces them.

• You're motivated by impact, not titles, and you want to be on the ground floor of something big.

What's On Offer

Our client doesn't hire average. They invest deeply in the right people.

• Top-of-market salary and OTE ($180,000–$250,000) depending on experience and performance.

• Equity opportunity – be part of the upside.

• Medical, dental, and vision insurance.

• 401(k) with employer match.

• Home office and tech stipend.

• Annual professional development stipend.

• Full WeWork membership for workspace access nationwide.

• Quarterly offsites and team summits.

You'll have every resource you need to thrive, from personalized training to leadership exposure to a product that truly sells itself once seen.

The Mission

Insurance is one of the last major industries not yet transformed by AI. This company is changing that, starting with customer communication.

Their AI voice, chat, and email agents already handle hundreds of thousands of policyholder calls, with instant response times and proven ROI for carriers and brokers. They help insurance teams grow revenue, improve service, and stay competitive in a market where the winners will be the ones who move fast.