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

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.

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