Enterprise Account Executive

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.