About FeatheryFeathery

About FeatheryFeathery is the AI Operating & Decisioning system for financial services. Our customers — including Fortune 500 insurers like Allstate — use Feathery to power mission-critical workflows across insurance underwriting, quoting, submission intake, claims, and customer onboarding. Why We’re Hiring

As Feathery grows, we’re expanding our footprint across the insurance industry and engaging with more enterprise carriers and insurance organizations that require a consultative, high-touch sales process. We’re hiring an Enterprise Account Executive with deep insurance industry experience to drive revenue growth and help define our enterprise sales motion within insurance. This role is ideal for someone who thrives in a full-cycle sales environment, enjoys building pipeline, and wants to play a key role in shaping how Feathery goes to market and wins within the insurance industry. About the Role

This is a high-ownership role that blends: What You’ll Do

Pipeline Generation & Prospecting

Prospect and develop recent 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 Deal Execution & Sales Process

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 Sales Strategy & Cross-Functional Collaboration





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 About You

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 Bonus

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 What We Offer

Competitive compensation and equity Health, dental, and vision coverage Unlimited PTO Downtown Toronto office location Office snacks and monthly catered lunch A supportive, low-ego team that values ownership and growth Company offsite to connect and recharge Feathery is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other legally protected characteristic. We’re committed to building an inclusive team and provide reasonable accommodations upon request.

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📌 Enterprise Account Executive - Insurance (Winnipeg)
🏢 Doist
📍 Winnipeg