Location:

In-office, San Francisco

About Strada

Strada is on a mission to reinvent how insurance carriers and brokers handle customer interactions across service, claims intake, and sales.

We 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 servicing to First Notice of Loss (FNOL) calls, Strada automates the routine so that teams can focus on what actually matters.

We’re growing incredibly fast and expanding our footprint with top carriers and brokers across the U.S. The opportunity is massive, and we’re looking for a driven Account Executive to help us 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 at Strada, 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 (we’ll train you on our process).

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.

Our Investment in You

We don’t hire average. We invest deeply in the right people.

• Top-of-market salary and uncapped OTE

• Meaningful equity stake with real upside.

• Medical, dental, and vision insurance.

• Gym membership.

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

About Strada’s Mission

Insurance is undergoing a once-in-a-generation AI transformation. We’re driving that change, starting with customer communication.

Our 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. We help insurance teams grow revenue, improve service, and stay competitive in a market where the winners will be the ones who move fast.

Compensation Range: $220K - $300K