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.