Portfolio Careers

Account Executive - Director of Enterprise Sales



Sales & Business Development
Toronto, ON, Canada
Posted on Thursday, June 22, 2023

The Account Executive is responsible for advising enterprise customers on how to utilize Owl’s solution most effectively to achieve business objectives. They lead the discovery process to understand clients’ challenges and pain points as they relate to Owl’s solution. The AE gathers customer feedback and requests while working with internal teams to help align our product roadmap. Effective communication with all stakeholders is essential, along with the ability to be flexible and versatile when handling new and withstanding ventures. This sales role requires a deep understanding of Enterprise Sales and how to drive the agenda for C-level executives of large insurance companies. This is a role best suited for those eager to hunt new deals and build new, multimillion $ enterprise level accounts.

Reports to: COO


  • Demonstrate a clear understanding of the key challenges our customers (L&H and P&C carriers in the US and Canada) face and how our claims management and fraud detection solutions solve them.
  • Manage and lead end-to-end process from lead generation to deep discovery and needs assessment, to actively drive the sales to closure
  • Actively develop new business in the US and Canada, strive to create new relationships
  • Build and maintain relationships with key technical & business decision makers (VP & up) at current and prospective client organizations.
  • Deliver compelling product demonstrations and presentations.
  • Develop meaningful relationships with industry partners to further mutual growth objectives.
  • Keep meticulous records in Salesforce.
  • Create and present accurate, realistic forecasts and unapologetically work through challenges with the team.
  • Deeply understand Owl’s offerings and present them to our prospects, demonstrating a knowledgeable expertise.
  • Prepare detailed quotations, proposals, RFP responses, executive summaries, etc. that exceed client expectations.
  • Represent the company at trade shows, conferences, industry meetings and virtual events to initiate and progress sales.
  • Research and develop a thorough understanding of the market, including prospects, partners and competitors, and work collaboratively with marketing, product development and other groups to maximize Owl’s offerings.
  • Minimum of 5 years’ successful enterprise sales experience in a SaaS startup. This includes a proven ability to exceed sales targets, along with a demonstrated understanding of the steps involved in a sales cycle.
  • Ability to leverage each stage of the sales cycle in order to advance sales.
  • Must be willing and able to travel at least 30-50% of the time.
  • Demonstrated ability to learn and apply proven sales methodologies.
  • Ability to seek out and build trusting relationships with executives of potential client organizations.
  • Must be comfortable sharing the product value proposition with both technical and non-technical executives.
  • Operate with a sense of urgency; be aggressive, competitive, and demonstrate a positive, winning attitude.
  • Superior time management skills and strong attention to detail.
  • Negotiate effectively, balancing value and time to close.
  • Demonstrate a high level of business/financial acumen and emotional intelligence.
  • Possess the ability to understand complex client strategies and tactical requirements, relating Owl’s offerings to develop solutions that deliver value specific to each client.
  • Understand current web and cloud technologies.
  • Utilize common desktop office and other business applications at an expert level.
  • Exceptional overall communication skills.
  • Wellness and Healthcare Spending Account
  • Fully paid extended health care plan
  • RRSP matching up to 4% of base salary
  • 4 weeks of vacation, 10 public holidays, plus 5 personal days
  • Weekly team lunches in the office
  • Amazing team of super talented individuals who make work a great experience