Enterprise Account Executive - Insurance (Canada)

The role

The Enterprise Account Executive will drive revenue growth and define the enterprise sales motion within the insurance industry. This role involves full-cycle sales, pipeline generation, and strategic consultative selling.

What you will do

• Prospect and develop new enterprise accounts across the insurance industry
• Reach out to prospects via email, phone, and LinkedIn
• Experiment with messaging, targeting, and channels to generate new opportunities
• Attend insurance industry conferences and events to build relationships and source pipeline
• Own pipeline generation strategy and continuously refine outbound approaches
• Manage the full sales cycle from initial outreach through close
• Handle inbound and referred leads and convert them into qualified opportunities
• Conduct discovery to understand customer needs and business challenges
• Deliver tailored demos and presentations for different stakeholders
• Navigate complex buying processes and multi-stakeholder deals

Required qualifications

• Experience selling enterprise SaaS into the insurance industry, or deep insurance industry experience in a commercial role
• Experience with enterprise deals ($100K–$1M+ ARR)
• Track record of high achievement in quota-carrying roles
• Strong consultative selling skills and ability to engage senior stakeholders
• Excellent communication and storytelling abilities with high customer empathy
• Experience building pipeline through outbound prospecting
• Builder mindset with a desire to shape processes and strategy
• Highly motivated, resilient, and comfortable operating in a fast-paced environment
• Passion for understanding customer problems and helping solve them

Nice to have

• Existing network within the insurance industry
• Experience selling complex or technical products
• Experience attending or sourcing pipeline through industry conferences
• Background at a high-growth B2B SaaS or InsurTech company

Benefits

• Competitive compensation and equity
• Health, dental, and vision coverage
• Unlimited PTO
• Office snacks and monthly catered lunch
• Company offsite to connect and recharge

About the company

Feathery is the AI operating system for financial institutions. It is a fast-growing leader in financial agentic automation.