Director of Sales (Toronto/Remote)

About the Role War Room is looking for an experienced Sales Director to join our growing team! Reporting to the CRO, you will take a hands-on role in driving revenue growth, building new client relationships, and positioning our services to meet client needs. This is currently an individual contributor role, focused on prospecting, pitching, and closing new business. As War Room grows, this role offers the opportunity to shape and scale our sales function, with the future potential to build and lead a high-performing team. This is a fully remote role based in Toronto, ON.

What You’ll Be Doing Revenue Growth: Own the sales process end-to-end — from prospecting and outreach through discovery, proposal development, and closing new business. Business Development: Identify and target new opportunities through research, networking, outbound outreach, and other creative lead-generation tactics. Consultative Selling: Understand client goals and challenges, positioning our digital marketing and technical services strategically to deliver results. Client Partnerships: Build strong, long-term relationships with clients, acting as a trusted advisor and ensuring seamless handoffs to account teams. Collaboration: Partner with technical and marketing experts to develop tailored proposals and ensure alignment with client objectives. Pipeline Management: Maintain a robust sales pipeline, prioritize effectively, and consistently meet or exceed revenue targets. Strategic Planning: Contribute to agency-wide growth strategies by identifying new market opportunities, shaping service offerings, and ensuring sales goals align with company vision. Department OKRs: Lead the development of sales department objectives and key results (OKRs), track progress, and report outcomes to ensure alignment with organizational priorities. Future Leadership: Establish the foundation for a scalable sales function by defining best practices, contributing to growth strategy, and preparing to mentor or lead a team as the company expands. Skills + Experience 10-12+ years of experience in sales or business development, with a proven record of winning new business and driving growth. 3-6 years of leading and developing a sales team Background in digital marketing, advertising, or technical services strongly preferred. Demonstrated success in closing complex deals through a consultative, strategic approach. Excellent communication and relationship-building skills. Highly organized and proactive, with strong pipeline management and prioritization abilities. Ability to thrive in an individual contributor capacity today, with the vision and leadership skills to step into team-building responsibilities in the future. Bonus Points Experience or exposure in programmatic advertising. Benefits & Perks 🏡 Fully Remote 🏖️ 3 weeks of annual paid vacation with tenure increases ❄️ Additional paid holiday season break 🤕 Paid sick leave 🏥 Extended Health and Dental benefits + Wellness spending account 📚 Professional development funding 🏦 Retirement savings matching

We appreciate your interest and application. Only those applicants under consideration will be contacted.

War Room is an Equal Employment Opportunity employer. Employment decisions are based on merit and business needs, and not on race, colour, creed, age, sex, gender, sexual orientation, national origin, religion, marital status, medical condition, physical or mental disability, military service, pregnancy, childbirth, and related medical conditions or any other classification protected by federal, state or provincial and local laws and ordinances.

Reasonable accommodation is available for qualified individuals with disabilities, upon request.

This role also includes a commission structure in addition to the base pay. The commission structure is uncapped and includes the ability to earn $45,000 in OTEs.