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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