Director of Enterprise Sales (New Business) in Canada at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director of Enterprise Sales (New Business) based in Canada.

The Director of Enterprise Sales will lead a high-performing team of enterprise sales professionals, driving new customer acquisition and revenue growth across organizations with more than 2,500 employees. Reporting to the VP of Sales, this strategic leadership role combines commercial vision, team development, and hands-on coaching to accelerate performance and expand market opportunities. You will oversee an established team of Account Executives while shaping sales strategy, improving deal execution, and strengthening forecasting practices. Working closely with Marketing, Product, and Customer Success, you will help build a cohesive go-to-market approach and identify new opportunities for growth. The role offers the opportunity to influence organizational strategy, scale enterprise sales operations, and foster a disciplined, collaborative, and results-oriented culture within a remote-first environment.

• Lead enterprise new business acquisition and take ownership of revenue performance against ambitious growth targets.

• Develop and execute initiatives to improve win rates, pipeline generation, sales velocity, and average deal size.

• Partner with Marketing to identify new revenue opportunities, explore additional markets, and expand industry reach.

• Manage and develop a growing team of Enterprise Account Executives, evolving team structures, management practices, and role specialization to improve focus and efficiency.

• Lead recruitment efforts in partnership with the talent team, from candidate sourcing and interviewing to hiring and closing high-performing enterprise sales professionals.

• Strengthen onboarding, training, and continuous development programs to accelerate ramp-up time and improve individual and team performance.

• Coach sellers directly through sales calls, deal reviews, strategic guidance, and actionable feedback, leveraging tools such as Gong and Lattice.

• Collaborate with senior leadership to establish targets, produce accurate forecasts, and report business performance to executive stakeholders and the Board of Directors.

• Establish a data-driven sales culture, using analytics to identify opportunities, monitor performance, and mitigate commercial risks.

• Build a culture of accountability, continuous learning, healthy competition, collaboration, and shared success while supporting team engagement and well-being.

• Strengthen cross-functional alignment with Product, Marketing, and Customer Success to ensure an effective go-to-market strategy.

• Monitor customer needs, market developments, competitive activity, and emerging SaaS sales practices to inform commercial strategy.

• Drive the adoption of AI tools and automated workflows to improve pipeline generation, account intelligence, deal execution, and sales coaching.

• At least 10 years of experience in B2B software sales, with a strong focus on new business acquisition.

• At least 3 years of experience in B2B Enterprise SaaS sales leadership at Director level or above.

• Demonstrated experience leading and developing a team of Enterprise Account Executives.

• A consistent track record of achieving and exceeding sales targets.

• Strong analytical capabilities and a metrics-driven approach to sales strategy, forecasting, and performance management.

• Thorough understanding of the RFP response process and the challenges organizations face when evaluating and purchasing enterprise software.

• A clearly defined leadership philosophy and the ability to communicate and apply it effectively.

• Experience with MEDDPICC and Command of the Message methodologies is preferred.

• A relevant bachelor's degree, ideally in a technical or business-related discipline.

• Additional assets: Experience selling to Sales and Marketing organizations, a record of published thought leadership, and experience scaling sales teams or supporting organizational growth from $50M to $100M in annual recurring revenue (ARR).

• Strong communication, coaching, strategic planning, and cross-functional collaboration skills.

• On-target earnings (OTE): CAD $288,000–$324,000, comprising base salary and commission.

• Equity participation.

• Commission-based compensation tied to sales performance.

• Remote-first work environment. Candidates must reside in the Greater Toronto Area or surrounding areas and be able to access a downtown Toronto coworking space for occasional team gatherings.

• Comprehensive health and wellness benefits starting on the first day of employment.

• Dedicated professional development and mastery allowance.

• MacBook laptop and monthly phone and internet subsidy.

• Work-from-home budget to support home office setup.

• Access to Claude and AI tools to support automation, experimentation, and productivity.

• Ongoing manager support through regular one-on-one meetings, feedback, and performance conversations.

• Opportunities to connect through company-wide town halls, Ask-Me-Anything sessions, celebrations, and employee resource groups.

• A supportive remote-first culture with opportunities for collaboration and professional growth.