Director of Sales

2 weeks ago

Toronto, Ontario, Canada TripSpark Technologies Full time

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Job Summary:

The Director of Sales is responsible for building a world-class, customer-focused sales organization. As a key member of the leadership team, this role oversees all aspects of sales operations—including forecasting, pipeline management, customer acquisition, and account expansion—while ensuring sales performance aligns with overall business objectives.

The Director of Sales will apply exceptional leadership and team-building capabilities to develop, coach, and mentor a high-performing sales team. They will guide the organization in identifying and cultivating opportunities across new and existing customers. This leader will drive the transformation needed for TripSpark Technologies to evolve into a stronger, more disciplined, consultative selling organization.

The ideal candidate brings deep experience in enterprise software sales and/or the public transit sector, with a proven ability to navigate complex procurement cycles, RFP processes, and multi-stakeholder decision environments.

Job Description:

About You

As the Director of Sales, your responsibilities will include, but are not limited to:

  • Delivering strong year-over-year bookings to drive sustainable organic growth.

  • Leading demand-generation efforts to build and expand a healthy sales pipeline.

  • Setting, achieving, and exceeding quarterly and annual sales quotas and objectives.

  • Partnering closely with Product and Marketing to ensure the sales team executes product strategy and integrates key actions into account plans and sales activity.

  • Cultivating a sales culture centered on delivering an exceptional customer experience.

  • Continuously assessing and adapting the sales coverage model (patches, resources, account teams, etc.) to maximize ROI and align with sales projections and results.

  • Measuring performance, coaching, mentoring, and top-grading the sales team to consistently achieve and surpass targets.

  • Reporting monthly on sales progress, activities, highlights, challenges, and market insights.

  • Establishing and reinforcing sales guidance and policy related to consultative selling, account planning, and required data capture.

  • Ensuring the accuracy of sales data (primarily within Salesforce), maintaining visibility up to 24+ months out.

  • Managing customer and sales team escalations by collaborating with peers and taking decisive, effective action.

  • Leading the team responsible for proposal development, including RFPs and Sole Source submissions.

  • Conducting deep market research and competitive analysis to evolve and strengthen sales practices.

  • Collaborating effectively with cross-functional peers to ensure customer needs are addressed and met.

About You

  • Bachelor's degree in Business Management or 10–15 years of equivalent enterprise sales experience.

  • Minimum of 5 years' experience leading a sales team with exceptional results.

  • Strong consultative sales acumen and a customer-focused leadership style.

  • Proven track record selling enterprise solutions, ideally within public transportation.

  • Demonstrated ability to build strong relationships and understand industry and client needs.

  • History of attracting, developing, and retaining top sales talent.

  • High-energy, results-oriented mindset with a competitive yet humble approach.

  • Self-starter who thrives in fast-paced environments.

  • Exceptional attention to detail and dedication to customer care.

  • Excellent presentation, executive engagement, negotiation, and communication skills.

  • Experience developing compensation plans and coaching value-based selling methodologies.

  • Strong background in account planning and execution.

  • Known for high drive, business acumen, work ethic, and metric-driven leadership.

  • Ability and willingness to travel approximately 50%.

What's In It for You?

  • Opportunity to work with a dynamic, innovative, passionate, and entrepreneurial team.

  • Open, inclusive, and collaborative company culture.

  • Competitive salary.

  • Participation in the Employee Stock Option Plan.

  • Comprehensive employee benefits package.

  • Flexible working hours.

Worker Type:

Regular

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