The Role

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 3× 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., ≥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.

• Equity → Share in the success you help create.
• Recharge → 4 weeks of vacation plus 1 week of personal/wellness days.
• Health & Well-being → Fully paid extended health and dental benefits in addition to $1200 annual wellness fund
• Financial Planning → RRSP program with generous matching.
• In person first collaboration office culture
• OTE includes base salary, equity & performance bonus: $220k - $300k