Account Executive to build and manage the sales cycle for an AI-native insurance startup. Collaborating closely with Founders, Marketing, and Customer Success teams for effective outreach and relationships.
Responsibilities
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
Requirements
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
Benefits
Competitive compensation
Base salary: $80,000 – $100,000
On-target earnings (OTE): $160,000 – $200,000
Uncapped commission structure and meaningful equity
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
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