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 setting

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

📌 Enterprise Account Executive (Winnipeg)
🏢 Feathery
📍 Winnipeg