About the RoleThis 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 DoPipeline 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
