Director, Software Sales- Upper Mid-Market

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

This leadership role is focused on driving revenue growth and expanding software adoption among upper mid-market customers. You will lead a high-performing sales organization, develop scalable sales strategies, and build repeatable motions that accelerate growth. The position combines strategic leadership, team development, enterprise relationship management, and operational excellence. You will partner closely with cross-functional teams including marketing, product, finance, and partnerships to deliver measurable business outcomes. This opportunity is ideal for a sales leader with deep SaaS or fintech experience who thrives in fast-paced environments. You will play a key role in shaping market expansion, strengthening customer relationships, and building a world-class sales function.

Accountabilities:: The Director of Software Sales - Upper Mid-Market will own the strategy, execution, and performance of the sales organization responsible for growing revenue across large mid-market customers. This role requires a strong commercial leader who can coach teams, optimize sales processes, build executive relationships, and consistently deliver against ambitious growth targets.

Lead, mentor, and develop a team of Software Account Executives responsible for closing complex, multi-stakeholder opportunities.

Own the annual revenue target for the upper mid-market segment and develop strategies to achieve and exceed sales objectives.

Build and execute scalable sales processes, methodologies, and operating frameworks to improve team performance.

Coach sales representatives through discovery, solution selling, ROI discussions, negotiations, closing strategies, and customer handoffs.

Serve as an executive point of contact for strategic prospects, supporting complex sales cycles and escalations.

Develop strong business cases that demonstrate value and address customer challenges through innovative software solutions.

Collaborate with Sales Development, Partner Sales, Marketing, Product, Sales Engineering, Finance, and Implementation teams to maximize growth opportunities.

Create and maintain sales KPIs, reporting structures, and operating rhythms to measure performance and identify improvement areas.

Monitor pipeline generation, conversion rates, forecasting accuracy, and overall sales execution.

Build strategic partnerships and co-selling opportunities that expand market reach and accelerate bookings.

Support product strategy by sharing market insights and customer feedback to strengthen product-market alignment.

Establish a culture of accountability, continuous improvement, and high performance across the sales organization.

Requirements:

The ideal candidate is an experienced SaaS sales leader with a proven ability to scale revenue teams, manage complex sales cycles, and build trusted relationships with senior business stakeholders.

7+ years of experience in fast-paced SaaS, software, or fintech environments.

5+ years of experience leading SaaS sales teams with measurable revenue responsibility.

3+ years of experience managing upper mid-market or enterprise sales teams.

Strong experience selling solutions to finance and technology leaders, including CFOs, VPs of Finance, Controllers, CIOs, CTOs, and related stakeholders.

Proven track record of exceeding sales quotas and delivering consistent revenue growth.

Experience implementing and coaching teams on structured sales methodologies and best practices.

Strong understanding of the complete sales lifecycle, from prospecting and discovery through negotiation, closing, and implementation.

Experience leading distributed teams across multiple functions and geographic regions.

Ability to establish operational rigor through metrics, forecasting, pipeline management, and performance analysis.

Strong relationship-building, communication, negotiation, and executive presence skills.

Comfortable using CRM platforms, sales analytics, and reporting tools to drive decision-making.

Experience in payments, financial technology, or accounts receivable solutions is a plus.

Highly motivated, organized, and action-oriented with a strong customer-focused mindset.

Benefits:

Competitive compensation package with a base salary range of approximately $160,000–$180,000 CAD.

On-target earnings (OTE) opportunity ranging from approximately $270,000–$300,000 CAD.

Fully remote work flexibility.

Opportunity to lead and scale a high-impact software sales organization.

Collaborative environment working with cross-functional teams across sales, product, marketing, and partnerships.

Opportunity to influence go-to-market strategy and revenue growth initiatives.

Career growth opportunities within a rapidly expanding technology environment.

Inclusive workplace culture focused on innovation, collaboration, and professional development.

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