Director of Professional Services

• Project Portfolio Management
  • Define and operationalize implementation methodologies appropriate for Enterprise Resource Planning (ERP), Point of Sale (POS), and Student Information System software implementations with contract values ranging from less than $10,000 to over $500,000 and durations from 1 month to 18 months
  • Lead PS team members in the execution projects and perform direct customer-facing project management duties as required.
  • Ensure successful project delivery aligned with revenue targets and client satisfaction.
  • Manage remote, cross-functional teams of Application Consultants, technical specialists, and SMEs across all product lines.
  • Apply project management frameworks with internal rigor while remaining approachable and relationship-centered in all customer-facing interactions, particularly with K-12 and higher-education institutional leaders.

• AI Strategy & Adoption
  • Treat AI adoption as a strategic imperative — embedding AI tools throughout the PS lifecycle from SOW creation and project planning through execution, testing, training, and closeout.
  • Leverage AI tools to scale implementation capacity, enabling a small PS team to support a growing number of large, complex projects without linear headcount growth.
  • Continuously evaluate and implement AI tools that accelerate project planning, automate documentation generation, and improve cross-project visibility.

Qualifications

• Proven experience leading complex software implementation projects in ERP, Point-of-Sale, Student Information Systems, or comparable vertical market software domains.
• Demonstrated success in building and scaling PS delivery processes from the ground up in a small-team, high-growth environment.
• Strong financial management capability, including hands-on experience with percent-complete (EAC) revenue recognition, PS P&L ownership, WIP management, and revenue forecasting.
• Demonstrated comfort operating a PS team at a revenue-to-operating-expense ratio of 2x or greater.
• Concrete, hands-on experience applying AI tools in a project management or PS delivery context, with the ability to speak to past applications, outcomes, and a forward-looking vision.
• Experience managing remote, cross-functional teams with accountability across distributed environments.
• Servant-leader with the ability to apply structured methodologies internally while remaining approachable and relationship-centered with K-12 and higher education customers.
• Results-driven, capable of defining relevant KPIs and milestones, then measuring progress to achieve long-term goals.

Preferred Qualifications

• Vertical market software experience; Education technology (K-12 and/or higher-education) considered a strong asset.
• Familiarity with IFRS revenue recognition policies.
• Experience with project tracking tools (e.g., Jira, Smartsheet, MS Project).
• Degree in Business Administration or Finance / Accounting, or equivalent operational experience.
• PMP or equivalent certification, applied with the flexibility appropriate to an education-sector customer base.

• • Apply AI to extract insight from project data – identifying delivery patterns, risk indicators, and customer engagement trends that inform operational and revenue decisions.
  • Lead change management efforts to embed AI into team workflows, with measurable adoption expectations and AI fluency as an explicit component of team performance.

• Revenue Expansion & Customer Growth
  • Identify and act on organic revenue expansion opportunities within the existing customer base, including additional implementation phases, training, consulting, and scope extensions.
  • Collaborate with Sales and Account Management to surface PS opportunities arising from customer interactions, implementation milestones, and product upgrades.
  • Support late-stage new-name sales opportunities by contributing detailed implementation plans, realistic timelines, and credible PS scoping to proposals and RFP responses.
  • Ensure methodology investments on early large-scale implementations are packaged to accelerate delivery – and PS revenue realization – on subsequent projects of similar scope.

• Financial Ownership
  • Own the Professional Services P&L across HHES and SDS, with accountability for sustaining a revenue-to-expense ratio of 2x.
  • Maintain rigorous monthly revenue forecasts based on scheduled project work, backlog, milestone billings, and in-month sales activity. 
  • Manage percent-complete (EAC) revenue recognition with accuracy, ensuring WIP balances are actively managed and forecasts reflect true project progress.
  • Ensure compliance with revenue recognition standards, including IFRS, across both simple and complex engagements.
  • Design project invoicing milestones that maintain healthy Working Capital across AR and WIP.
  • Track and report KPIs including PS Ratio, utilization, effective hourly rate, and forecast accuracy.

• Process Development & Scaling
  • Design scalable delivery frameworks, tracking tools, and standardized documentation for each product line, building on the organization’s existing AI-generated template assets.
  • Develop methodology explicitly designed to scale implementation volume from approximately 2 large projects annually to 6–10, within the current team structure.
  • Create commercially sound, operationally realistic Statements of Work and formal project documentation for both customer-facing and internal/sales purposes

• Team Leadership & Strategic Contribution
  • Mentor and support a team of Application Consultants with AI fluency as an explicit and measurable component of performance expectations.
  • Set clear performance standards, conduct regular evaluations, and own PS team recruiting.
  • Serve as a key member of the business unit leadership team, contributing to tactical and strategic planning across SDS and HHES.
  • Support Sales and Marketing through RFP responses, implementation methodology documentation, and go-to-market materials that differentiate the organization’s delivery capabilities.

Salary range: $110,000.00 – $125,000.00 CAD per year