Enterprise Account Executive managing complex deals with Fortune 500 companies. Leading the full sales cycle and building relationships with C - level executives in retail and consumer goods.
About the role
- Enterprise Account Executive managing complex multi-stakeholder sales cycles for AI-driven insurance solutions. Focused on business case development and closing strategic accounts in North America.
Responsibilities
- 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
Requirements
- 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
Benefits
- 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
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