Director Regional Sales/ RVP

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director Regional Sales / RVP based in Canada. This leadership role is responsible for driving sales performance across a significant Canadian customer and prospect portfolio. You will set regional strategy, lead execution, and guide a team of sales professionals toward quarterly and annual revenue objectives. The position combines strategic planning, sales leadership, pipeline management, customer engagement, and team development. You will build executive-level relationships and identify opportunities to expand existing accounts through cross-selling, upselling, and demand creation. Working in a consultative software-sales environment, you will partner with customers, sales teams, and senior leadership to accelerate growth. This is a fully remote, full-time opportunity with approximately 50% travel required.

Develop and execute the regional sales strategy and vision in alignment with senior leadership, company strategy, and annual business plans. Lead, manage, motivate, and develop multiple sales professionals, ensuring teams consistently meet or exceed assigned sales quotas and performance expectations. Own the regional sales pipeline and drive opportunities through the sales process from prospecting and qualification through negotiation and closure. Identify, prospect, qualify, and close new business opportunities while supporting Account Executives in complex sales negotiations. Build and maintain strategic relationships with customers and prospects, particularly key and executive-level accounts, to maximize business opportunities. Establish clear objectives, assign responsibilities, and maintain accountability across virtual sales teams. Forecast sales accurately and provide regular weekly updates and detailed pipeline insights to sales leadership using agreed tools and processes. Deliver quarterly and annual sales revenue targets while maintaining focus on core performance metrics. Mentor, coach, and develop sales professionals, supporting their growth and strengthening overall team capabilities. Oversee sales-team hiring, development, and performance management in line with organizational needs. Ensure sales processes and methodologies are clearly understood, consistently followed, and effectively applied across the region. Develop market and segment strategies and provide structured reporting on key opportunities, emerging markets, and growth initiatives. Work directly with sales professionals to develop territory plans focused on demand creation, account penetration, cross-selling, and upselling. Participate in sales calls and product or solution demonstrations when appropriate, providing hands-on sales leadership and coaching. Serve as a role model for organizational culture, collaboration, accountability, and customer focus. Requirements Bachelor’s degree required; MBA, MA, or equivalent professional experience is preferred. 12+ years of overall sales experience, including at least 8 years in sales leadership within the software or related technology industry. Proven experience selling software solutions and managing complex B2B sales cycles. Demonstrated leadership experience with a strong record of performance management, coaching, and professional team development. Ability to operate effectively at both strategic and operational levels, translating business strategy into measurable sales execution. Established relationships and contacts with potential customers and business stakeholders. Strong consultative selling capabilities and exceptional interpersonal skills, particularly when engaging executive-level customers and partners. Proven track record of generating sales in new product or new market environments. Experience with sales methodologies, sales funnel management, and CRM platforms, preferably Salesforce. Exceptional written, verbal, presentation, and communication skills across a wide range of audiences. Proven ability to interact effectively with C-level and other senior management stakeholders. Strong team-management, customer-facing, negotiation, and relationship-building capabilities. Demonstrated ability to identify, develop, and retain high-performing sales talent. Collaborative and results-oriented leadership style with the ability to build a strong team environment. Willingness and ability to travel approximately 50% of the time. Successful completion of applicable background screening processes may be required, including employment, education, criminal, sanctions, and other checks as permitted by applicable regulations. Benefits Full-time, fully remote opportunity based in Canada. Competitive compensation aligned with senior sales leadership responsibilities. Opportunity to lead regional sales strategy and influence significant customer and prospect relationships. High level of visibility with senior leadership and executive-level customers and partners. Opportunity to manage, mentor, and develop experienced sales professionals. Exposure to strategic software sales, consultative selling, new-market development, cross-selling, and upselling. Opportunity to contribute directly to regional growth and quarterly and annual revenue objectives. Approximately 50% business travel, providing opportunities for customer and partner engagement. Collaborative, team-oriented environment focused on professional development, accountability, and customer relationships.

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