Enterprise Account Executive
$220,000 - $300,000/year
23 Oct 2025
Verified by Turrior
Content + Source + Freshness • 12 Dec 2025 • 95% confidence
82 / 100
Offer value
Offers solid value due to the strategic nature of the sales function and compensation potential linked directly to performance.
- Highly compensated role with performance bonuses.
- Strategic contributions to company growth in Insurtech sector.
- Remote flexibility with expectation for regional engagement.
Pros
- Attractive compensation package linked to performance.
- Dynamic role with opportunities to significantly impact company growth.
- Strong industry exposure to Insurtech and healthcare markets.
Cons
- Requires adaptability to complex enterprise sales cycles.
- Performance pressure to consistently meet sales targets.
- Possible travel requirements can impact work-life balance.
Who it's for
Mid to Senior Level • Remote with regional travel
Good fit
- Experienced sales executives with SaaS background.
- Candidates willing to thrive on targets and performance metrics.
- Individuals with a knack for building and maintaining relationships.
Not recommended for
- New sales professionals or those lacking enterprise sales experience.
- Individuals who prefer structured hours with minimal travel.
- Professionals uneasy with high-stakes negotiations or closing deals.
Motivation fit
Desire to sell innovative technology products.Interest in engaging with C-suite stakeholders.Passion for building relationships and navigating complex sales cycles.
Key skills
Enterprise sales strategyCustomer relationship managementNegotiation and closing skillsCommunication and presentationSales forecasting
Score: 82/100 AI verified analysis
About the job
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
