Job Description

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 closehandoff. 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.,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

EquityShare in the success you help create.
Recharge4 weeks of vacation plus 1 week of personal/wellness days.
Health & Well-beingFully paid extended health and dental benefits in addition to $1200 annual wellness fund
Financial PlanningRRSP program with generous matching. In person first collaboration office culture * OTE includes base salary, equity & performance bonus: $220k - $300k