Director – Head of Sales Operations

This is a fully remote position, open to applicants in Canada, +1 more state.

📋 Description

• Lead the annual and quarterly sales planning for territory, capacity, quota, and compensation strategies.

• Create well-balanced territories and account segmentation, model headcount requirements, and establish quotas linked to forecast goals.

• Collaborate with Finance and People teams on compensation strategy.

• Assist in go-to-market planning for new product offerings.

• Oversee the forecasting process and schedule for new business, renewals, and expansion efforts.

• Define pipeline hygiene standards, stage definitions, and inspection routines.

• Conduct weekly pipeline and forecast reviews with Sales leadership.

• Work alongside Finance to reconcile bookings with revenue, manage campaign delivery pacing, and prepare quarterly business reviews.

• Develop and maintain reporting systems for pipeline metrics, win/loss statistics, retention and renewal rates, upsell opportunities, rep productivity, and overall brand and agency performance.

• Present commercial insights to senior leadership and maintain a single source of truth for commercial data.

• Manage the sales technology stack, which includes Salesforce, forecasting tools, enablement platforms, data enrichment, and workflow software.

• Define and implement an AI strategy utilizing AI agents, predictive analytics, and intelligent automation.

• Promote CRM adoption and ensure data quality while designing workflows that minimize manual seller effort.

• Assess, pilot, evaluate, and scale new AI tools.

• Oversee deal desk operations, including pricing governance, approval workflows, proposal support, and order processing.

• Enhance quote-to-cash processes and establish rules of engagement across Sales, Client Experience, and Market Development.

• Scale sales best practices across outreach cadences, deal processes, and renewal strategies.

• Collaborate with Sales Enablement and Training to integrate process changes and best practices.

• Lead, develop, and mentor the Sales Operations team.

• Act as a trusted operating partner to senior Finance, Client Experience, and Sales leaders.

⛳️ Requirements

• Bachelor's degree is mandatory.

• 10+ years of experience in sales operations, revenue operations, or commercial strategy.

• 3+ years of experience in leading the function or a significant portion of it.

• Previous experience in people management is required.

• Extensive, hands-on knowledge of Salesforce, including administration, reporting, and process design.

• Experience in managing forecasting, territory and quota planning, and designing sales compensation within a quota-carrying sales organization.

• Background in media, advertising, point-of-care marketing, life sciences, or healthcare technology is preferred.

• Familiarity with annually renewing or re-sold revenue models is advantageous.

• Strong analytical skills, including practical experience using AI tools for analysis, forecasting, and workflow automation.

• Experience with Salesforce Einstein/Agentforce, generative AI assistants, or similar technologies.

• High proficiency in Excel or Google Sheets.

• Proficiency in SQL and Power BI or similar BI tools is preferred.

• Ability to distill complex data into a clear, compelling narrative for executives.

• Proven record of scaling a commercial function through AI and automation.

• Excellent cross-functional collaboration and communication skills.

• Comfortable working at both strategic and operational levels.

• Located in EST or CST in Canada or the U.S.

• Willingness to travel occasionally for client meetings, industry events, conferences, and team collaboration.

🏝️ Benefits

• Base salary along with variable incentives.

• Comprehensive Total Rewards package.

• Fully remote work opportunity.

• Reimbursement for home office expenses.

• Monthly reimbursements for cell phone, internet, and wellness expenses.

• Competitive compensation package.

• Flexible PTO and company holidays.

• A variety of healthcare benefits for employees, families, and pets starting on day one.

• Generous parental leave benefits with top-up.

• Reimbursement for continuing education and professional certifications.

• Various offsite events and activities for team bonding and connection.

• Local in-person volunteer events and community engagement programs.

• Company-wide recognition program with redeemable points and a catalog of rewards.

• Employee Resource Groups (ERGs) for support and networking.

• Accommodations available upon request for candidates participating in the selection process.