Vice President, Territory Sales

Softchoice•Toronto, ON

3d•Hybrid

About The Position

The Vice President, Territory Sales Division (TSD) is responsible for driving sustainable, recurring revenue growth across Softchoice’s small-to-medium business customer segment. This role leads a large, distributed sales organization operating in a hybrid sales model and is accountable for delivering predictable performance, exceptional customer outcomes, and a strong, engaged sales culture. The VP, TSD owns the execution of Softchoice’s modern go-to-market strategy, with a clear emphasis on software-led growth, services attachment, hybrid cloud adoption, and digital-first selling. This leader is expected to be a proven operator in the SMB digital sales world—bringing current market practices, playbooks, and AI-enabled selling approaches that elevate how the organization sells and serves customers.

Requirements

10+ years of progressive B2B sales experience, with 7+ years in senior sales leadership roles.
Proven success leading large, complex sales organizations in a technology, software, cloud, or services-led environment.
Demonstrated experience leading SMB digital selling (inside/remote/inbound), including building and scaling digital motions, operating cadence, and performance management at scale.
Demonstrated experience owning and executing an organization-wide digital and AI strategy, with evidence of measurable impact on productivity, conversion, and customer outcomes.
Strong track record of driving growth through recurring revenue models, services attachment, and customer expansion.
Strong commercial and analytical acumen, with experience managing to P&L metrics and using leading indicators to drive forecast accuracy.
Demonstrated ability to translate strategy into executable programs, change adoption, and measurable results.
Highly effective coach and people leader with a passion for developing leaders and building high-performance culture.
Executive presence, with the ability to influence across functions without direct authority.
Bachelor’s degree required; MBA or equivalent experience preferred.

Responsibilities

Own and deliver revenue, gross margin, and direct contribution targets across monthly, quarterly, and annual planning horizons.
Lead the execution of the Territory Sales go-to-market strategy, prioritizing software subscriptions, hybrid cloud solutions, and professional and managed services.
Drive customer acquisition and expansion through a lifecycle approach that spans land, adopt, expand, and renew.
Establish and maintain strong pipeline health, forecast accuracy, and gap-to-plan management using data-driven insights and leading indicators.
Design and launch sales programs, plays, and initiatives that scale growth, improve productivity, and increase recurring revenue.
Ensure consistent use of sales methodologies, tools, and KPIs to drive predictable outcomes.
Own the digital sales vision and AI-enabled go-to-market strategy for the SMB segment, ensuring digital motions (inbound, inside, remote, and self-serve where applicable) are embedded in core sales execution.
Bring modern, external best practices in SMB digital selling—playbooks, tooling, and operating rhythms—so the organization accelerates capability without needing to “learn it from scratch.”
Translate digital and AI strategy into measurable commercial outcomes by using data and analytics to track impact on pipeline creation, conversion, cycle time, productivity, and customer penetration.
Champion adoption of AI-powered sales practices and tools by fostering a culture of innovation, experimentation, and continuous learning; set clear expectations and accountability for usage.
Lead cross-functional alignment across Sales, Digital Strategy, Marketing, and Enablement by removing barriers and accelerating execution of digital and AI initiatives.
Provide leadership to the Director, Digital Sales by setting outcomes, metrics, and operating cadence for scaling digital and AI capabilities.
Champion a customer-first mindset focused on long-term value, adoption, and retention (not transactional selling).
Partner closely with Marketing, Professional Services, Managed Services, Customer Success, Finance, and Partner teams to deliver integrated, outcome-based solutions.
Align demand generation, sales execution, and service delivery to ensure a seamless customer experience.
Represent the voice of the SMB customer internally, ensuring go-to-market decisions reflect evolving market needs.
Lead, coach, and develop Directors and Managers through regular 1:1s, deal reviews, performance coaching, and strategic planning.
Build a strong leadership bench through intentional succession planning and development of high-potential talent.
Create a high-performance sales culture grounded in accountability, trust, inclusion, and continuous improvement.
Support career progression, capability development, and retention of Territory Account Executives and leaders.
Foster strong engagement through visible leadership, clear expectations, and consistent recognition.
Establish and maintain a disciplined operating cadence, including weekly, monthly, and quarterly business reviews.
Leverage data, analytics, and modern sales technology to drive insight-led decision-making.
Continuously refine sales processes, territory planning, and coverage models to improve efficiency and scale.
Lead change effectively as the sales model evolves, ensuring clarity, alignment, and adoption across the organization.
Balance operational excellence with innovation by testing new approaches to selling, engagement, and enablement.