Vice President, Territory Sales (Software)

TL;DR

Vice President, Territory Sales (Software): Driving sustainable recurring revenue growth across the SMB customer segment with an accent on software-led growth, hybrid cloud adoption, and digital-first selling. Focus on implementing AI-enabled selling approaches, scaling digital sales motions, and leading a large distributed sales organization.

Location: Toronto, ON, Canada

Salary: $254,900 - $318,500 (Base) + 53.85% target incentives

Company

hirify.global is a software-focused IT solutions and services provider that equips organizations to be agile and innovative through cloud migration and digital workplace transformation.

What you will do

• Deliver revenue, gross margin, and direct contribution targets across monthly, quarterly, and annual planning horizons.
• Execute the Territory Sales go-to-market strategy, prioritizing software subscriptions and hybrid cloud solutions.
• Develop and lead the digital sales vision and AI-enabled GTM strategy for the SMB segment.
• Manage pipeline health, forecast accuracy, and gap-to-plan using data-driven insights and leading indicators.
• Coach and develop a leadership bench of Directors and Managers to build a high-performance sales culture.
• Align demand generation, sales execution, and service delivery through cross-functional partnership with Marketing and Customer Success.

Requirements

• 10+ years of progressive B2B sales experience, with 7+ years in senior sales leadership roles.
• Proven success leading large, complex sales organizations in technology, software, cloud, or services-led environments.
• Demonstrated experience scaling SMB digital selling motions (inside, remote, and inbound).
• Evidence of executing organization-wide digital and AI strategies with measurable impact on productivity.
• Strong commercial and analytical acumen with experience managing P&L metrics.
• Bachelor’s degree required; MBA or equivalent experience preferred.

Culture & Benefits

• Comprehensive health and wellbeing package, including medical and dental care.
• Financial security through RRSP/DPSP retirement savings plan with company matching.
• Flexible work arrangements allowing you to plan workdays in a way that suits you best.
• Extensive paid time off, including vacation, sick leave, parental leave, and volunteer days.
• Award-winning inclusive culture recognized as a Great Place to Work for 20 consecutive years.