Vice President, Territory Sales

Why you’ll love Softchoice:

We are a software-focused IT solutions and services provider that equips organizations to be agile and innovative, and for their people to be engaged, connected, and creative at work. That means moving them to the cloud, helping them build the workplace of tomorrow, and enabling them to make smarter decisions about their technology. By doing these things we help them create success for their customers and their people.

We stand proudly for our people and support their success through career development and advancement. We are recognized and respected for our culture of inclusion and belonging, continuously striving to do what’s good for our people and communities. 
 

The impact you will have:

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.

What you will do:

1. Sales Strategy and Business Performance

• 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.

2. Digital and AI Sales Vision and Strategy

• 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.

3. Customer-Centric and Cross-Functional Leadership

• 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.

4. People Leadership, Coaching and Succession

• 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.

5. Operating Rigor and Continuous Improvement

• 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.

Success Measures

• Achievement of revenue, margin, and direct contribution targets.
• Scaled adoption of digital selling motions and AI-enabled sales practices across the sales organization, with measurable productivity and conversion lift.
• Growth in software, hybrid cloud, and services mix and recurring revenue.
• Strong pipeline coverage, forecast accuracy, and sales productivity.
• Customer retention, expansion, and overall experience.
• Leadership bench strength, engagement scores, and voluntary attrition.
• Consistent execution of sales processes, tools, and operating cadence.

What you will bring to the table:

• 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.

Compensation:

A reasonable estimate of the current base pay range for this position is $254,800 to $350,350 + 53.85% as target incentives.

Actual salary will be based on a variety of factors, including location, experience, skill set, education, and related certifications. The range for this position in other geographic locations may differ. 

Softchoice offers a comprehensive and competitive benefit plan to all full-time employees, which includes:

• Health and Wellbeing: Medical and Dental Care, Employee & Family Assistance Program
• Financial Benefits: RRSP/DPSP Retirement Savings Plan with Company Matching, Life and Disability Insurance
• Paid Time Off: Vacation and Sick Leave, Holidays, Parental Leave, Volunteer Days, Bereavement Leave
• Additional Perks: Employee Discount Program

Not sure if you qualify? Think about applying anyway:

We understand that not everyone brings 100% of the skills and experience for the role.

At Softchoice, we offer opportunities to a diverse group including those with a variety of workplace experiences and backgrounds.  Whether you are new to corporate tech, returning to work after a gap in employment, or looking to transition and take the next step in your career, we are excited to learn more about you and encourage you to apply.

Why You’ll Love Working Here:

• The People: You’ll thrive in our collaborative environment, surrounded by incredible colleagues who foster support and innovation, driving our collective success
• High-Performing Culture: At Softchoice, we are dedicated to achieving our goals and committed to success for our customers and each other
• Flexibility: Plan your workdays in a way that suits you best
• Award-Winning Workplace: Proudly recognized as a Great Place to Work for 20 consecutive years
• Inclusive Culture: We are committed to an inclusive culture where every team member can be their authentic self
• Competitive Benefits: Benefit from competitive perks that start on day one

Inclusion & Equal opportunity employment:

We are an equal opportunity employer committed to diversity, inclusion & belonging. People seeking employment at Softchoice are considered without regard to any protected category including but not limited to, race, color, religion, national origin, age, sex, marital status, ancestry, disability, veteran status, gender identity, or sexual orientation.

Require accommodation? We are ready to help:

We are proud to provide interview & employment accommodation during the recruitment and hiring process. If you require any accommodation to apply or interview for a position, please reach out directly to asktalentacquisition@softchoice.com. We are committed to working with you to best meet your needs.

Our commitment to your experience:

We are committed to the safety of all applicants and team members. With that in mind, we have implemented digital interviewing for everyone. We understand that you may need to interview with distractions around you (such as children or furry friends) and we will be doing the same.

Before you start with us, we will conduct a criminal record check, verify your education, and check your references.

When you join Softchoice, we will onboard you remotely. Don't worry. It's quick, simple and you'll be connected with your new team in no time.

Job Requisition ID: 7441 

EoE/M/F/Vet/Disability  

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