Vice President, Software Sales (SaaS)

TL;DR

Vice President, Software Sales (SaaS): Own bookings attainment across iMotor Websites, Matador AI, and Statistical Surveys with an accent on building and scaling high-performing sales organization. Focus on revenue execution, pipeline management, team coaching, and cross-functional alignment with Product and Finance.

Location: Toronto, ON

Company

Digital marketplace business building value in buying and selling across automotive, powersports, RV, marine, and equipment industries as part of global CAR Group with 2,500 team members worldwide.

What you will do

• Own ARR bookings targets and drive revenue execution through forecasting, pipeline management, and deal inspections across three product lines.
• Lead, coach, and develop Product Specialists and SDRs with structured 1:1s, performance plans, and enablement frameworks.
• Establish 3x pipeline coverage, optimize demo-to-conversion, and enforce qualification methodologies.
• Collaborate with Product, Finance, Marketing, and Customer Success on GTM strategy, AOP, and handoffs.
• Develop channel partnerships, co-sell motions, and represent at industry events.

Requirements

• 8–12+ years SaaS sales experience including 3–5+ years senior leadership with quota ownership.
• Track record leading teams to quota attainment in SMB/mid-market ($15K–$100K ACV).
• Expertise in consultative selling (Challenger), Salesforce, pipeline management, and forecasting.
• Experience as cross-functional stakeholder in Product and Financial processes.
• Executive presence for C-suite presentations.

Nice to have

• Multi-product SaaS sales leadership in dealership verticals (automotive, powersports, etc.).
• Experience with Websites, AI/messaging, CRM/DMS, or survey SaaS products.
• Building channel/partner programs.

Culture & Benefits

• Inclusive environment prioritizing people with real impact opportunities.
• Up to 31 days paid time off in first year, flexible leave, continuing education via LinkedIn Learning.
• Full benefits: medical, dental, vision, 401K match, wellness program.
• Global exposure via CAR Group Tour across Australia, Brazil, Chile, South Korea.