Enterprise Account Executive - Insurance

About FeatheryFeathery 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 HiringAs 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 RoleThis 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 DoPipeline 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.
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