Job Description
Feathery automates data intake workflows for enterprise companies across financial services, healthcare, and other regulated industries. Customers use Feathery to power mission-critical workflows like insurance underwriting, client onboarding, account openings, loan origination, and patient intake.
With rapid revenue growth and increasing enterprise adoption, we’re scaling our go-to-market team to expand into larger accounts and new verticals.
Why We’re Hiring
As Feathery grows, we’re engaging with more enterprise customers who require a consultative, high-touch sales process.
We’re hiring an Enterprise Account Executive to drive revenue growth and help define our enterprise sales motion. 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 the go-to-market strategy of a fast-growing B2B SaaS company.
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 (outbound + inbound)
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 key verticals (e.g., insurance)
Reach out to prospects via email, phone, and LinkedIn
Experiment with messaging, targeting, and channels to generate new opportunities
Attend 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 SaaS in 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
Experience selling into financial services or other regulated industries
Existing network within insurance, wealth management, or related verticals
Experience selling complex or technical products
Experience attending or sourcing pipeline through industry conferences
Background at a high-growth B2B SaaS 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, ****** 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.
