We are looking for an Enterprise Account Executive with 4–6 years of SaaS sales experience to join Owl.co as an IC hunter who can run and close complex, multi-stakeholder enterprise cycles. You'll be the second Enterprise AE on the team, reporting directly to the CEO, building pipeline, shaping opportunities with clear business cases, and landing strategic accounts at some of the largest insurance carriers in North America. This is a high-ownership startup role where you'll sell a production-deployed AI platform that is the market leader in Claims Intelligence with 100% customer retention.
What will you be doing?
Own the full sales cycle from discovery → solution mapping → business case → security/legal → close → handoff, carrying a $2.25M NNARR annual quota
Build and manage a 3× pipeline coverage target through outbound hunting, supported by 2 BDRs for lead generation
Run executive-level conversations with insurers (CCO/CFO/CIO and line-of-business leaders), tailoring narratives around ROI and business outcomes
Collaborate cross-functionally with Product, CS, and Tech to scope pilots, define success criteria, and convert to production contracts
Represent Owl.co at industry events and customer onsites, contributing feedback loops to refine ICP, messaging, and competitive positioning
Owl.co is the leading Claims Intelligence platform, building applied AI systems for high-stakes, real-world decisions in the insurance industry. Their technology is deployed in production at some of the largest carriers in North America, helping insurers unlock insights, prioritize claims, and explore best practices with unprecedented accuracy and efficiency.
Owl.co's mission is to facilitate insurance leaders in creating a new future for their industry — one anchored in a true partnership between humans and AI. They call this Claims Intelligence: equipping teams with insightful knowledge to liberate their creativity and intuition so they can deliver accountable, effective, and ethical results for claimants.
Culture & Values:
Owl.co is a Series B company backed by top-tier VCs including Cota Capital, Sorenson Ventures, Luge Capital, and others, with over $30 million in funding. The company is led by experienced founders who have steered previous businesses to successful exits, and their technical leadership comes from Meta, Microsoft, X, and Goldman Sachs.
Salary
$140,000 - $175,000
Location
Vancouver, Canada
Experience
4+ years
Total raised
$40.0M
Last stage
Series B
Investors
No applications, no recruiter spam. Just the intro.
A few questions to make sure this role is the right shape for you. Two minutes.
I write the intro, send it to the founder, and handle the back-and-forth.
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.