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Loopio

Director of Enterprise Sales – New Business

Loopio

. Lead the Enterprise Sales team and report directly to the VP of Sales .

Posted 11/4/2026full-timeToronto • CanadaLeadWebsite

Core Competencies

Role fit
Core Competencies

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Demonstrates extensive experience in B2B Enterprise SaaS sales leadership, focusing on new business acquisition and team development. Proven ability to set and exceed revenue targets while leveraging analytics and strategic partnerships to drive organizational growth.

Highest-signal resume keywords
B2B Software SalesEnterprise SaaS LeadershipTeam DevelopmentAnalytics-Driven Decision MakingMEDDPICC Experience

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
New Business AcquisitionRevenue Target AchievementRFP Response ProcessSales ForecastingMetrics-Driven ApproachDeal Strategy ReviewsSaaS Sales ToolsAI Tools AdoptionPipeline GenerationAccount Intelligence
Soft Skills
Leadership StyleCoachingCollaborationCommunicationCultural Fostering
Tools & Technologies
GongLattice
Industry Keywords
B2BEnterprise SalesThought LeadershipOrganizational GrowthGreater Toronto Area

About the role

Key responsibilities & impact
  • Lead the Enterprise Sales team and report directly to the VP of Sales
  • Acquire new customers and achieve revenue targets
  • Optimize win rates, opportunity generation, deal velocity, and deal size
  • Partner with Marketing to identify new revenue opportunities, markets, and industry segments
  • Oversee and scale the Enterprise seller team, structure, hierarchy, and communication mechanisms
  • Implement strategic role specialization to improve team focus and efficiency
  • Partner with Talent Experience to recruit and hire enterprise sales talent
  • Optimize onboarding and continuous training programs
  • Coach sellers through calls, deal-strategy reviews, and actionable feedback using Gong and Lattice
  • Set targets, develop sales forecasts, and report progress to senior leadership and the Board of Directors
  • Use analytics to identify opportunities and mitigate risks
  • Foster a culture of discipline, learning, competitiveness, collaboration, and celebration
  • Align Product, Marketing, and Customer Success around the go-to-market strategy
  • Monitor team engagement, challenges, and well-being
  • Monitor customer, market, and competitive trends
  • Align Product Management and Sales
  • Track SaaS sales tools, trends, and best practices
  • Drive adoption of AI tools and automated workflows for pipeline generation, account intelligence, deal execution, and coaching

Requirements

What you’ll need
  • 10+ years in B2B software sales, focused on new business acquisition
  • 3+ years in B2B Enterprise SaaS software leadership at Director level or above
  • Experience leading a team of Enterprise Account Executives
  • Track record of setting and exceeding targets
  • Deep analytical abilities and metrics-driven approach
  • Strong understanding of the RFP response process and company challenges
  • Well-defined leadership style that can be articulated clearly
  • Relevant Bachelor’s degree, preferably in a technical or business function
  • Experience with MEDDPICC and Command of the Message would be ideal
  • Experience selling to Sales and Marketing organizations is a strong asset
  • History of published thought leadership is a strong asset
  • Experience scaling a sales team and contributing to organizational growth from $50M to $100M ARR is a strong asset
  • Must reside in the Greater Toronto Area and surrounding areas
  • Must be able to access the Downtown Toronto co-working space for occasional team get-togethers
  • Must be legally authorized to work in Canada without employer sponsorship

Benefits

Comp & perks
  • Professional mastery allowance for learning and development
  • Health and wellness benefits starting day one
  • MacBook laptop
  • Monthly phone and internet subsidy
  • Work-from-home budget
  • Claude account for experimentation and automation
  • Remote-first flexible work environment
  • Virtual team connection opportunities
  • Town halls, AMAs, and company celebrations
  • Employee Resource Groups
  • Award-winning workplace
  • Equity
  • Commission