Account Executive

Pathwork is redesigning life & health insurance jobs for the AI age. We believe the 2.5M professionals in the $1T life and health insurance industry don’t need better tools; they need a new operating system.

Pathwork’s first solution streamlines the pre-application process in the life and health insurance industry. By removing friction from early case work, brokers can operate with greater speed, accuracy, and precision, giving them a competitive edge like never before.

We’ve already proven it:

• 80+ top brokerages and national carriers use Pathwork

• Active pilots with multiple top-10 insurance companies

• 150%+ QoQ growth, every quarter since launch
  

Pathwork was built from day one as AI-native, combining automation and intelligence to transform insurance distribution and bring speed, structure, and clarity to outdated workflows.

• Category-defining product already in use by national brokerages and insurers

• Funding from top VCs

• Deep founder experience: Work closely with experienced founders who’ve built and scaled companies from zero to exit in insurance and AI

• Early team, high ownership: You’ll shape the brand, the function, and the category

• High-Trust & Long-term Oriented: Grow with a team that values trust, authenticity, learning, and lasting impact. Your contributions will help shape our product, culture, and long-term legacy

We’re hiring our first Account Executive, a hunter who can own the full sales cycle from prospect to close. You’ll report to the Head of Revenue and work closely with the Founders, Marketing, and Customer Success teams to create a category-defining sales motion.

As the first AE, you’ll have the chance to shape how we sell, who we sell to, and how we expand across the industry. This role is ideal for a hungry IC who loves building pipeline, closing deals, and laying the foundation for a world-class sales team.

• Build and manage a full sales cycle, from prospecting to close

• Develop and refine outreach strategies for SMB and mid-market brokers

• Qualify inbound leads and convert them into opportunities
  

• Create pipeline through outbound prospecting, networking, and events

• Consistently hit or exceed quarterly revenue targets

• Track performance metrics and report on sales activity

• Deliver compelling demos and presentations tailored to broker and carrier needs

• Build trusted relationships with prospects, helping them understand the impact of Pathwork’s solutions

• Partner with Customer Success to ensure smooth handoffs and long-term success

• Collaborate with Marketing to refine messaging, campaigns, and collateral

• Provide feedback to Product to help shape the roadmap

• Option to grow into leadership, with the opportunity to mentor future AEs and help scale the team

• Have 2–6+ years of experience in SaaS sales or insurance, with a track record of closing deals

• Experience selling into SMB and mid-market accounts (insurance or financial services strongly preferred)

• Thrive in chaos, energized by building process while scaling growth and not intimidated by ambiguity

• Like getting your hands dirty, from cold outreach to closing six-figure deals

• Strong verbal and written communication skills, with the ability to tailor messaging to regulated audiences

• Want to be part of something bigger, shaping not just a sales motion but a category, a company, and the future of insurance distribution

• Major plus: experience selling to insurance brokers, carriers, or adjacent industries

• Bonus: comfortable running both high-velocity deals and consultative sales processes

• Competitive compensation

  • Base salary: $80,000 – $100,000

  • On-target earnings (OTE): $160,000 – $200,000

  • Uncapped commission structure and meaningful equity

• Employee-centric benefits including:

  • High 401K match and FSA program

  • Modern, employer-paid health benefits designed to support you on your terms

• Real ownership, autonomy, and direct collaboration with the Founders & Head of Revenue

• A chance to define a category, shape the sales motion from the ground up, and work across multiple audiences

• Hybrid culture: NYC & SF offices, or remote for the right candidate