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.

• 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.

• 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.

• Comprehensive medical, dental, and vision insurance.
• Flexible time off and paid holidays.

• Highlight specific enterprise deals you closed, especially any involving operations or claims teams, and quantify the impact where possible.
• Prepare a concise case study that shows how you used HubSpot to manage a complex pipeline and improve forecast accuracy.
• Demonstrate familiarity with insurance workflows; research common pain points in claims handling and quote intake before interviews.
• When answering scenario questions, emphasize your consultative approach and ability to translate technical features into business outcomes.
• Ask about the product‑feedback loop with engineering; showing interest in shaping the roadmap signals you understand the advisor role.
• If offered equity, request clarification on vesting schedule and any performance milestones tied to the role.
• Watch for vague compensation language; be ready to negotiate based on the high‑value ACV deals you’ll be responsible for.