Drive enterprise insurance sales at Feathery from its downtown Toronto office, using consultative selling and outbound pipeline generation skills.

As an Enterprise Account Executive, you will own full-cycle sales across the insurance industry. You will build prospects, execute complex deals, and engage senior stakeholders through tailored discovery, demos, and presentations. The role also includes collaboration with product, engineering, marketing, and leadership.

Key Responsibilities:
Prospect current enterprise insurance accounts through outbound channels
Generate pipeline using email, phone, LinkedIn, and events
Manage sales cycles from outreach through closing
Conduct discovery and deliver tailored stakeholder presentations
Refine sales playbooks,



positioning, and go-to-market processes

Requirements:
Enterprise SaaS sales or deep commercial insurance experience
Experience managing enterprise deals from $100K to $1M+ ARR
High achievement in quota-carrying sales roles
Solid consultative selling and senior stakeholder engagement skills
Excellent communication, storytelling, and customer empathy

Bring insurance expertise, enterprise deal execution, and pipeline-building discipline to Feathery’s growing revenue engine.
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📌 Enterprise Insurance Sales Executive Toronto
🏢 Feathery
📍 Toronto