Regional Vice President, Enterprise Sales - Remote Eligible

Regional Vice President, Enterprise Sales In Canada

This role is a senior sales leadership position responsible for driving enterprise revenue growth and building high-performing account teams across a broad territory. The Regional Vice President, Enterprise Sales will lead strategic initiatives, manage pipeline, and coach teams to exceed targets in a competitive and fast-paced environment. You will leverage data, AI tools, and modern sales methodologies to optimize execution and accelerate deal cycles. This position offers the opportunity to influence regional strategy, engage executive-level customers, and foster a culture of performance and accountability. The role combines hands-on deal leadership with strategic oversight, providing significant impact on business growth and team development. It's ideal for a leader with a proven record in complex enterprise sales and a passion for developing top-tier sales talent.

Accountabilities:

• Lead, coach, and develop a team of Strategic Enterprise Account Executives, setting clear expectations and driving consistent execution across the region.
• Own pipeline, forecast, and revenue performance, ensuring disciplined execution and consistent attainment of growth goals.
• Build a performance-driven, high-accountability culture, establishing operating rhythms and competitive sales practices.
• Implement strong pipeline inspection and forecasting discipline, ensuring quality deal qualification and visibility.
• Stay engaged with key deals, providing hands-on guidance in strategy, qualification, and execution.
• Drive regional go-to-market execution leveraging data, AI insights, and account prioritization to focus on high-value opportunities.
• Act as an executive sponsor for strategic accounts, developing relationships with senior stakeholders and ensuring business impact.
• Collaborate cross-functionally with Marketing, Customer Success, Partners, and Product to align strategy and support customer outcomes.

Requirements:

• 10+ years of experience in enterprise SaaS or cloud-based sales with a proven record of closing complex, multi-threaded deals.
• 5+ years of experience leading high-performing enterprise sales teams in competitive environments.
• Strong experience implementing and reinforcing formal sales methodologies such as MEDDPICC and strategic account planning frameworks.
• Demonstrated ability to engage and influence C-level executives (CIO, CTO, and equivalent).
• Experience operating within partner-led or partner-influenced go-to-market models.
• Analytical, data-driven mindset with experience leveraging AI and sales intelligence tools for territory planning, pipeline management, and team productivity.
• Excellent coaching, mentoring, and talent development skills to elevate team performance.
• Strong executive presence, communication, and negotiation skills.

Benefits:

• Competitive base salary ($188,150 – $215,000 USD) plus variable compensation plan.
• Comprehensive health, dental, and vision coverage.
• Generous parental leave policies and unlimited vacation policy.
• Access to wellness programs and Employee Assistance Programs.
• 401K with company matching and Lifestyle Spending Account.
• Remote work flexibility with collaboration opportunities in regional hubs.
• Opportunity to lead strategic growth and develop high-performing enterprise sales teams.