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 current enterprise insurance accounts through outbound channelsGenerate pipeline using email, phone, LinkedIn, and eventsManage sales cycles from outreach through closingConduct discovery and deliver tailored stakeholder presentationsRefine sales playbooks, positioning, and go-to-market processesRequirements:

Enterprise SaaS sales or deep commercial insurance experienceExperience managing enterprise deals from $100K to $1M+ ARRHigh achievement in quota-carrying sales rolesStrong consultative selling and senior stakeholder engagement skillsExcellent communication, storytelling, and customer empathyBring insurance expertise, enterprise deal execution, and pipeline-building discipline to Feathery’s growing revenue engine.

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