About Feathery Feathery 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.
As an early member of the team, you’ll have significant ownership over pipeline, deals, and how we win in the enterprise.
About the Role This is a high-ownership role that blends:
Full-cycle enterprise sales across the insurance industry

Pipeline generation and deal execution

Strategic, consultative selling

Cross-functional collaboration with product, marketing, and leadership

You’ll own the entire sales process - from sourcing opportunities to closing deals - while helping define how Feathery scales its enterprise revenue engine.
What You’ll Do Pipeline Generation & Prospecting Prospect and develop current 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 (Ontario)
🏢 Feathery
📍 Ontario