Strategic Sales Director, Canada - Growth & Execution

Sales Director (Managing Director – Sales & Operation Management)

Highspring – Professional Services & Technology Transformation

About Highspring

Highspring is a professional services firm that helps organizations achieve their business objectives through technology-driven transformation. We partner with enterprises across Cloud, Data, Cybersecurity, GenAI, Digital Engineering, and Enterprise Modernization to accelerate delivery, strengthen internal capabilities, and drive measurable business outcomes.

Sales Director (Managing Director – Sales & Operation Management)

Highspring – Professional Services & Technology Transformation

About Highspring

Highspring is a professional services firm that helps organizations achieve their business objectives through technology-driven transformation. We partner with enterprises across Cloud, Data, Cybersecurity, GenAI, Digital Engineering, and Enterprise Modernization to accelerate delivery, strengthen internal capabilities, and drive measurable business outcomes.

As part of our next phase of growth, we are hiring a Sales Director – Canada to lead company-wide commercial performance and play a central role in scaling the organization.

Role Summary

The Sales Director (Managing Director – Sales Management) is a senior business leader responsible for owning Highspring’s commercial performance and acting as the operational and strategic backbone of the organization.

This role goes beyond traditional sales leadership. It is designed for an executive who can lead sales, influence delivery and talent, build scalable structures, and orchestrate execution across the business, while working closely with the partnership on enterprise growth and strategic relationships.

Key Responsibilities

• Commercial Strategy & Revenue Growth
• Own and execute the company’s commercial growth strategy.
• Partner with the Managing Partner to expand enterprise accounts, develop new markets, and strengthen go-to-market execution.
• Lead forecasting, pipeline governance, revenue performance tracking, and sales accountability.
• Drive execution discipline across sales, delivery, and recruiting to ensure growth translates into results.
• Sales Leadership & Performance
• Lead, structure, and elevate Account Managers, Engagement Managers, Account Owners, and Sales Leaders.
• Implement and continuously evolve scalable sales frameworks, account planning methodologies, and performance KPIs.
• Build a high-performance, ownership-driven sales culture with clear expectations and outcomes.
• Business Scaling & Operational Alignment
• Ensure the organization is operationally ready to support growth by aligning sales demand with delivery capacity and recruiting pipelines.
• Design and implement scalable operating models, processes, and governance appropriate for the $40M–$100M+ growth stage.
• Work closely with Practice Leaders, Operations, and Talent Acquisition to align capacity with demand.
• Improve margin performance, utilization, and operational predictability.
• Establish consistent leadership cadence and cross-functional alignment.
• Talent Development & Leadership Enablement
• Build structured career paths and leadership frameworks across sales and operations.
• Implement coaching, performance management, and succession planning.
• Support senior leaders in building depth and sustainability across teams.
• Partnerships & Market Ecosystem
• Develop and manage strategic partnerships with technology vendors, delivery partners, and subcontractors.
• Identify ecosystem opportunities that support growth and capability expansion.
• Strengthen Highspring’s market position through partner-led strategies.
• Client Success & Account Expansion
• Ensure consistent delivery of value aligned with client business objectives.
• Drive customer satisfaction, renewals, and account expansion.
• Partner with Practice Leaders to improve service maturity and consistency.
• Partner with Practice Leaders to strengthen and evolve service offerings by defining clear use cases, value propositions, and go-to-market narratives aligned to client needs.
• Leadership, Culture & Accountability
• Act as a visible, inspiring leader who brings structure, clarity, and momentum.
• Set high standards for accountability, communication, and execution.
• Reinforce Highspring’s values and leadership expectations across the organization.

Professional Experience

Ideal Background & Experience

• 10–20+ years in professional services, consulting, or technology services.
• Direct experience scaling a services organization from approximately $40M to $100M+ in revenue.
• Strong background in sales leadership, commercial management, and revenue operations.
• Demonstrated ability to align sales growth with delivery, recruiting, and operational capacity.
• Experience building sales organizations, leadership frameworks, and performance models.
• Proven success working with senior enterprise clients.

Core Competencies

• Executive presence and inspirational leadership
• Strong commercial and financial acumen (pipeline, margin, forecasting)
• Strategic thinker with operational discipline
• Excellent communication and stakeholder management skills
• Ability to unify cross-functional teams around shared goals
• Entrepreneurial mindset with experience navigating scale-up complexity

Why This Role Is Different

• You are not building from zero, you are professionalizing and scaling
• You operate at a critical inflection point where structure, rigor, and leadership matter
• You influence the entire business, not just sales
• You help shape the next chapter of Highspring’s growth

Determining compensation for this role (and others) at Vaco/Highspring depends upon a wide array of factors including but not limited to the individual’s skill sets, experience and training, licensure and certifications, office location and other geographic considerations, as well as other business and organizational needs. With that said, as required by local law in geographies that require salary range disclosure, Vaco/Highspring notes the salary range for the role is noted in this job posting. An applicant may also be eligible to participate in certain incentive compensation programs based on achieving certain performance targets set forth each year and subject to the incentive compensation plan’s terms and conditions. The individual may also be eligible for discretionary bonuses, and can participate in medical, dental, and vision benefits as well as the company’s 401(k) retirement plan.

Salary Range for this role:: $150,000 CAD - $250,000 CAD

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