Enterprise Account Executive - Insurance

Feathery•Toronto, ON

4d•Onsite

About The Position

Feathery is seeking an Enterprise Account Executive with deep insurance industry experience to drive revenue growth and help define our enterprise sales motion within insurance. This role involves full-cycle enterprise sales, pipeline generation, deal execution, and strategic, consultative selling. The ideal candidate will have experience selling enterprise SaaS into the insurance industry or significant commercial experience within the insurance sector. As an early member of the team, you will have significant ownership over pipeline, deals, and go-to-market strategy. You will own the entire sales process, from sourcing opportunities to closing deals, and contribute to shaping Feathery's enterprise revenue engine.

Requirements

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 Haves

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

Responsibilities

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
Help define and refine sales playbooks, positioning, and processes
Partner with product and engineering to communicate customer needs and influence roadmap
Collaborate with marketing on campaigns and demand generation initiatives
Contribute to product launches and go-to-market strategy