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Director, Enterprise Sales, North America

7 hours, 31 minutes ago
Canada
Full-time
Executive
Head of Sales
Sales and Business Development
Apply Now
360Learning

360Learning

360Learning offers a comprehensive digital learning platform that empowers organizations to collaboratively create, deliver, and enhance training courses, leveraging data and AI to engage learners and trainers while facilitating continuous upskilling f...

Diversified Consumer Services
201-500
Founded 2010
$243M raised
View All Jobs 45

Description

  • Lead and coach a team of four Enterprise Account Executives.
  • Own Enterprise North America pipeline management, forecasting, territory strategy, and quarterly sales performance.
  • Run rigorous weekly pipeline and forecast reviews and provide clear visibility to the Chief Sales Officer.
  • Support and escalate complex commercial cycles, including 6- and 7-figure ARR deals.
  • Assess Account Executive performance and implement proactive coaching through call preparation, live deal support, and debriefs.
  • Partner with BDRs to qualify opportunities and deepen discovery of prospect business needs.
  • Collaborate with Pre-sales, Product, Alliances, and Professional Services teams to advance deals.
  • Use partner and alliances ecosystems to accelerate new-logo acquisition.
  • Analyze market and business trends to prioritize deals and set segment strategy.
  • Help hire and onboard new Account Executives as the team scales.

Requirements

  • 3+ years of top-performing sales leadership experience in software or SaaS.
  • Direct experience managing Enterprise Account Executives.
  • Demonstrated success closing or supporting complex strategic deals in the 6- to 7-figure range.
  • Experience with HR solutions (preferred).
  • Strong coaching ability to identify individual strengths and development areas.
  • Data-driven, detail-oriented approach to pipeline management and forecasting.
  • Comfort operating hands-on in commercial cycles, including escalations and direct deal support.
  • Experience collaborating with Pre-sales, Product, and Professional Services teams.
  • Experience leveraging partner or alliances ecosystems for new-logo acquisition.
  • Ability to hire, onboard, and enable Account Executives; willingness to travel for prospect meetings and trade shows.
  • Strong written and verbal English communication skills and comfort working asynchronously.

Benefits

  • Base salary, variable incentive pay, and company equity.
  • Comprehensive health insurance from the first day of employment.
  • RRSP contribution matching.
  • Generous parental leave.
  • Unlimited annual PTO, five sick days, and Ontario statutory holidays.
  • Remote-first work environment with flexible hours.
  • Professional development through the 360Learning platform.
  • Employee resource groups supporting mental health, sustainability, parents, LGBTQIA2S+, women, and ethnic diversity.

Interested in this position?

Apply directly on the company website

Apply Now

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