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 opportunities, 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 new 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 Robust 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.

📌 Enterprise Insurance Sales Executive (Toronto)
🏢 Feathery
📍 Toronto