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.

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Enterprise Account Executive