Enterprise Account Executive

We’re building applied
AI systems for high-stakes, real-world decisions. Our platform ingests and reasons over large, messy data to surface evidence with hard constraints around fairness, auditability, and low bias.
The single gnarliest, most impact‑heavy place this problem shows up is in insurance claims, so that’s where we’re deployed today, running in production at some of the largest carriers in North America.
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 withstrong 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 Leadershi p: 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
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