About Strada

Strada is building the agentic workforce for insurance operations.

Our agents take calls, send texts, and answer emails, then complete the work: quoting new business, servicing policies, processing claims. They connect directly into the core systems insurers already run on, which is why they finish the job instead of routing it to a human.

Backed by Y Combinator and top-tier investors, Strada already automates millions of customer interactions for national carriers, third-party administrators, wholesalers and brokers representing $20B+ in annual premiums.

It is now certain that AI in insurance operations will become a multi-billion dollar category. The question is not if, but who wins. We are already ahead in deploying AI at scale and are defining the category.

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 Enterprise Account Executive at Strada, you’ll own the sales process end-to-end, from discovery to close, with some of the most respected brands in the insurance space.

Your day will include:

• Driving new business with Operations, Claims, and Transformation leaders at large insurance carriers, brokers, wholesalers, and TPAs.

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

You Bring

• 5+ years of B2B enterprise sales experience, with a proven track record of exceeding quota.

• Experience selling technical products to operations leaders, preferably in the insurance industry.

• A strong understanding of complex sales processes with 6-figure to 7-figure ACVs.

• A consultative approach and meticulous attention to detail, simplifying complexity, and earning trust.

• A growth mindset, hungry to learn, iterate, and drive to perfect your GTM strategy.

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

Bonus Points For

• Experience selling enterprise software to the insurance industry.

• Founding sales team or early-stage startup experience.

Who You Are

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

• You thrive in ambiguity and early-stage environments.

• You're a natural relationship builder and establish rapport by understanding your prospects through diligent preparation.

Our Investment in You

• Top-of-market salary and uncapped OTE

• Meaningful equity stake with significant upside.

• Comprehensive medical, dental, and vision insurance.

• Flexible time off and paid holidays.