Head of Sales Operations

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director, Head of Sales Operations based in Canada.

• Lead annual and quarterly sales planning across territories, capacity, quotas, account segmentation, and compensation, while supporting go-to-market planning for new offerings.
• Own the forecasting process across new business, renewals, and expansion, establishing pipeline standards, inspection rhythms, and regular forecast reviews with Sales leadership.
• Partner with Finance on bookings-to-revenue reconciliation, campaign delivery pacing, and quarterly business reviews.
• Build and maintain commercial reporting covering pipeline, win/loss performance, retention, renewals, upsell, representative productivity, and account or agency performance.
• Establish and govern a single source of truth for commercial data and translate complex information into actionable insights for senior leadership.
• Own the sales technology ecosystem, including Salesforce, forecasting, enablement, data enrichment, workflow tools, integrations, vendor relationships, and roadmap planning.
• Define and execute an AI roadmap using AI agents, predictive analytics, and intelligent automation to improve forecasting, identify deal risks and next-best actions, reduce manual work, and increase seller productivity.
• Drive CRM adoption, data quality, and scalable workflows while evaluating emerging AI technologies, piloting practical use cases, measuring results, and expanding successful solutions.
• Oversee deal desk activities, including pricing governance, approval workflows, proposal support, and order processing in collaboration with Legal, Finance, and Client Experience.
• Continuously improve quote-to-cash processes and rules of engagement across Sales, Client Experience, and Market Development.
• Identify effective sales, outreach, deal, and renewal practices and scale them across the organization in partnership with Sales Enablement and Training.
• Lead, mentor, and develop an established Sales Operations team covering analytics, systems administration, and deal support.

• Bachelor’s degree required, with 10+ years of experience in sales operations, revenue operations, or commercial strategy and at least 3 years leading the function or a significant portion of it.
• Demonstrated people management experience and the ability to lead teams across analytics, systems, and commercial operations.
• Deep hands-on expertise with Salesforce, including administration, reporting, and process design; broader revenue technology stack ownership is an advantage.
• Proven experience with forecasting, territory and quota planning, and sales compensation within a quota-carrying sales organization.
• Experience in media, advertising, point-of-care marketing, life sciences, healthcare technology, or similar environments; familiarity with annually renewing or re-sold revenue models is a plus.
• Strong analytical capabilities, including practical experience using AI tools for analysis, forecasting, workflow automation, or similar applications.
• Experience with tools such as Salesforce Einstein/Agentforce, generative AI assistants, or comparable AI technologies is valuable.
• Advanced proficiency with Excel or Google Sheets; SQL and Power BI or similar business intelligence tools are preferred.
• Ability to transform complex commercial data into clear, compelling narratives and recommendations for executive audiences.
• Demonstrated ability to scale commercial functions through AI and automation, including identifying use cases, driving adoption, and measuring productivity impact.
• Excellent communication and cross-functional collaboration skills, with the ability to operate effectively at both strategic and hands-on levels in a fast-growing environment.

• Fully remote work model for employees based in EST or CST in Canada or the U.S.
• Base compensation of $200,000–$230,000 CAD, depending on experience, inclusive of base salary and variable incentive.
• Comprehensive total rewards package designed to support employees both professionally and personally.
• Home office expense reimbursements.
• Flexible paid time off and 8 company holidays.
• Monthly reimbursement for cell phone, internet, and wellness expenses.
• Generous parental benefits for employees in Canada.
• Variety of insurance coverage, including options that extend to pets.
• Continuing education and professional certification reimbursement.
• Opportunities to participate in Employee Resource Groups.
• Occasional travel opportunities for client meetings, industry events, conferences, and team collaboration.