Director – Head of Sales Operations

This is a fully remote position, open to applicants in United States, +1 more country.

📋 Description

• Lead the annual and quarterly sales strategy across territory, capacity, quota, and compensation planning.

• Design equitable territories and account segmentation, model headcount requirements, and establish quotas aligned with forecast objectives.

• Collaborate with Finance and People teams on compensation strategies for new business, renewals, and upselling efforts.

• Support go-to-market strategies for new offerings, including engagement rules, coverage, and launch objectives.

• Manage the forecasting process and cadence for new business, renewals, and expansion initiatives.

• Set pipeline hygiene standards, stage definitions, and review rhythms.

• Conduct weekly pipeline and forecast evaluations with Sales leadership.

• Partner with Finance on the reconciliation of bookings to revenue, campaign delivery pacing, and quarterly business assessments.

• Create and sustain reporting for pipeline, win/loss ratios, retention and renewal rates, upselling, representative productivity, and brand- and agency-level performance.

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

• Oversee the sales technology stack, including Salesforce, forecasting tools, enablement resources, data enrichment, and workflow applications.

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

• Promote CRM adoption and enhance data quality while designing workflows that minimize manual effort for sellers.

• Evaluate, pilot, assess, and scale emerging AI tools.

• Manage deal desk operations, including pricing governance, approval workflows, proposal assistance, and order processing.

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

• Identify and propagate sales best practices across outreach strategies, deal motions, and renewal tactics.

• Collaborate with Sales Enablement and Training to implement process changes, tools, and best practices.

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

• Act as an operational partner to Finance & Commercial Operations, Client Experience, and Sales leadership.

⛳️ Requirements

• Bachelor’s degree is mandatory.

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

• At least 3 years of experience in leading the function or a significant part of it.

• Previous people management experience is required.

• Extensive, hands-on expertise in Salesforce, including administration, reporting, and process design.

• Experience 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.

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

• High proficiency in Excel or Google Sheets.

• Familiarity with SQL and Power BI or similar BI tools is preferred.

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

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

• Exceptional cross-functional collaboration and communication skills.

• Comfortable operating at both strategic and operational levels in a rapidly growing business.

• Must be available to work in EST or CST time zones in Canada or the U.S.

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

🏝️ Benefits

• 100% remote work with home office expense reimbursements.

• Competitive salary package.

• Flexible PTO along with 8 company holidays.

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

• 100% paid 12-week parental leave for U.S. employees.

• Generous parental benefits for employees in Canada.

• A variety of insurance options for employees (and their pets!).

• Continuing education and professional certification reimbursement opportunities.

• Chance to join an Employee Resource Group.

• Occasional travel for client meetings, industry events, conferences, and team collaboration.

• Base salary and variable incentives.

• Comprehensive Total Rewards package.