Director, Head of Sales Operations

Accountabilities: • 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.

Requirements

• 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.

Benefits

• 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.

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