Enterprise Account Executive - Insurance (Canada)

About Feathery

Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader in financial agentic automation. Industry leaders like Tokio Marine, Sequoia Financial, and Cerity Partners run their client-facing workflows on Feathery, from onboarding and risk assessment to reconciling systems and generating proposals and reports.

At the center of it all is Robin, our AI operations assistant. Robin scans client documents, configures and deploys workflows, assists users in their day-to-day work, takes notes during meetings, and supports a growing range of operational tasks across the client lifecycle.

We're building a future where financial operations shift from paperwork, manual data entry, and disconnected systems to intelligent, automated workflows that let firms spend their time on clients instead of process. We're proud to be backed by world-class investors who share that vision, including Portage Ventures, Allstate Ventures, and Index Ventures, among others.

We're driven by a shared commitment to excellence and velocity. Our values — Own the Problem, Grit Beats Gloss, Say It Straight — shape how we work and grow as a team.

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 new 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.