Enterprise Account Executive

AI overview

Collaborate across multiple teams to drive complex enterprise cycles and influence strategic accounts while sharing in the success through equity and performance bonuses.

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.

Benefits

  • 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

Perks & Benefits Extracted with AI

  • Equity Compensation: Equity → Share in the success you help create.
  • Health Insurance: Fully paid extended health and dental benefits in addition to $1200 annual wellness fund
  • Generous RRSP matching: RRSP program with generous matching.
  • Paid Time Off: 4 weeks of vacation plus 1 week of personal/wellness days.
  • Remote-Friendly: In person first collaboration office culture

We know, insurance may not seem like the most sexy of industries. However, insurance is a social good and affects nearly every facet of the daily lives of billions of people. Because of the scale, the challenges are enormous, complex, and complicated—those challenges require the very best engineering talent to create elegant solutions to address them.If you’re the kind of person who wants to use your talent to solve wicked-hard problems that affect billions of people all over the world, and do it in an ethical way that protects their rights and privacy, and do that working with a kick-ass team who wants to do the same, to be treated respectfully, have your voice heard, give balance to your life, find opportunities to grow, teach and lead, and have stability—drop us a line. We’re growing. Fast.Or you can use those mad skills to put mustaches on cats—just sayin’.Here are the team members we’re looking for:

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Salary
CAD $220,000 – CAD $300,000 per year
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