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
