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.