Director, Mid-Market Sales

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director, Mid-Market Sales based in Canada.

This role offers the opportunity to lead and scale a high-performing sales organization within a fast-growing technology environment. You will be responsible for driving revenue growth, developing sales leaders, and creating strategies that deliver measurable business impact. The position combines strategic leadership, team development, operational excellence, and customer-focused selling. You will coach experienced sales professionals while building a culture centered on collaboration, accountability, and continuous improvement. Working with cross-functional teams, you will influence go-to-market strategies and help expand solutions that support essential industries. This opportunity is ideal for a sales leader who thrives in complex environments and enjoys building teams that achieve ambitious goals. You will have the autonomy to make impactful decisions while contributing to the long-term growth of a global organization.

Accountabilities:: As a Director, Mid-Market Sales, you will lead a team of sales managers and account executives while driving revenue performance, sales strategy, and organizational growth. You will combine leadership, coaching, and analytical decision-making to build a scalable sales function and strengthen customer engagement.

Coach and develop a team of 6–8 sales managers by providing strategic guidance, pipeline support, and performance coaching.

Lead hiring efforts for sales managers and account executives, ensuring effective onboarding, development, and long-term success.

Drive sales strategy and execution to achieve quarterly revenue targets and business objectives.

Partner with cross-functional teams to solve complex business challenges and manage strategic initiatives.

Create and deliver ongoing sales training, enablement content, and professional development programs.

Provide actionable feedback and coaching to improve sales performance and strengthen team capabilities.

Build a culture of collaboration, accountability, inclusion, and continuous growth across the commercial organization.

Use data-driven insights to evaluate performance, identify opportunities, and optimize sales processes.

Champion company values and encourage a customer-focused, high-performance team environment.

Requirements:

The ideal candidate is an experienced sales leader with a strong background in managing complex sales organizations, developing teams, and driving revenue growth within technology or enterprise environments.

10+ years of sales experience with a proven track record of managing complex sales cycles from prospecting through close.

3+ years of experience managing sales teams supporting the US market.

Demonstrated success leading full-cycle B2B sales motions and exceeding revenue targets.

Strong experience coaching outbound sales teams and developing high-performing sales professionals.

Deep understanding of complex enterprise sales processes involving multiple stakeholders and longer decision cycles.

Excellent leadership, communication, presentation, and stakeholder management skills.

Strong interpersonal abilities with experience building trust and motivating diverse teams.

Ability to adapt quickly, operate independently, and thrive in a fast-changing environment.

Data-driven mindset with the ability to translate insights into strategic decisions.

Experience providing upward feedback and influencing leadership teams.

Familiarity with Salesforce or similar CRM platforms.

Benefits:

Competitive annual on-target earnings range of CAD $341,000–$409,200.

Performance-based compensation structure with opportunities for additional rewards.

Equity opportunities for eligible roles within a high-growth organization.

Flexible remote-first working model for candidates based in Canada.

Comprehensive health and wellness benefits.

Parental leave and employee support programs.

Professional development stipend to support ongoing learning and career growth.

Opportunity to lead impactful teams and influence business strategy.

Collaborative environment focused on innovation, ownership, and long-term success.

How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best!  Why Apply Through Jobgether?    Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.     #LI-CL1