We're hiring an
IC hunter who can run and close complex, multi-stakeholder enterprise cycles. You'll build pipeline, shape opportunities with clear business cases, and partner cross-functionally to land and expand strategic accounts. If you thrive in ambiguity, love discovery, and can sell both product and outcomes, you'll fit right in.
What you'll do:- Own the full cycle from discovery solution mapping business case security/legal close handoff.
- Build and manage a 3x pipeline coverage target with a disciplined methodology
- Run executive-level conversations with insurers and ecosystem partners; tailor narratives to CCO/CFO/CIO and line-of-business leaders.
- Collaborate with Product, CS, and Tech to scope pilots, define success criteria, and convert to production.
- Forecast with precision in Salesforce; maintain clean hygiene across CRM
- Contribute feedback loops to marketing and product; help refine ICP, messaging, and competitive positioning.
- Represent Owl at industry events (e.g., Insurtech-focused conferences) and customer onsite meetings as needed.
Ideal profile:- 4-6 years of SaaS new-logo experience; at least 2+ years selling into enterprise (multi-stakeholder, security/legal cycles).
- Exposure to Insurtech / P&C insurance or adjacent regulated industries (bonus: carrier, TPA, SIU, claims tech).
- Consistent quota attainment (e.g., 60;100% in 2 of last 3 years) with meaningful new-logo wins.
- Comfortable selling an outcomes-driven narrative (business case, ROI, value mapping) as well as product capabilities.
- Mastery of discovery, qualification, and exec presence; challenger mindset with strong storytelling.
- Located in Vancouver & willing to work East Coast hours; able to travel ~10-20% for customers and team onsites.
Nice to have:- Established network with carriers
- Experience selling AI/data/analytics platforms or workflow tools.
- Familiarity with procurement, InfoSec, and DPA/MSA negotiation in regulated environments
Benefits:- Industry Leaders: Our technical leadership comes from Meta, Microsoft, X, and Goldman Sachs, bringing world-class expertise to our agile team.
- Market Leadership: We hold the largest market share in our space, offering a proven ROI and maintaining a 100% customer retention rate, with renewals consistently doubling their previous terms.
- Lean & Impact Driven Team: Our small, nimble team makes swift decisions and encourages direct communication and innovation through a flat organizational structure. You'll make real, meaningful contributions right from the start.
- Established Product-Market Fit: AI-Driven Product that helps shape an AI-powered enterprise solution for insurance companies across the US and Canada.
- Healthcare benefits: we cover 100% of the premiums for you and your family members (medical, dental & vision)
- RRSP matching to help you save for your future
- Recharge: 4 weeks of paid time off & 5 additional personal/sick days
- Daily team lunches
- Bi-annual offsites: we'll make sure everyone at Owl has an opportunity to can hang out with teammates IRL at least twice a year
Department Sales Locations Vancouver Remote status Hybrid Yearly salary CAD220,000 - CAD300,000 Employment type Full-time
