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

Vaco, LLC (“we,” “our,” or “Vaco”) respects your privacy and is committed to providing a transparent notice of our Notice at Collection and Privacy Policy for California Residents. This Notice and Privacy Policy for California Residents applies solely to those who reside in the State of California (“consumers” or “you”). For additional details, click here.

California residents may also access Vaco’s HR Notice at Collection for California Applicants and Employees.

Vaco is an Equal Opportunity Employer and does not discriminate against any employee or applicant for employment because of race (including but not limited to traits historically associated with race such as hair texture and hair style), color, sex (includes pregnancy or related conditions), religion or creed, national origin, citizenship, age, disability, status as a veteran, union membership, ethnicity, gender, gender identity, gender expression, sexual orientation, marital status, political affiliation, or any other protected characteristics as required by federal, state or local law.

Highspring

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