Director of Professional Services

• Project Portfolio Management
  • Define and operationalize implementation methodologies appropriate for Enterprise Resource Planning (ERP)Point of Sale (POS) andStudent Information System software implementationswith contract valuesranging from less than $10000to over $500000and 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 orcomparablevertical market software domains.
• Demonstrated success in building and scaling PS delivery processesfrom 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 intoteam 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 milestonesthat 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 organizations existing AI-generated template assets.
  • Develop methodology explicitly designed to scale implementation volume from approximately 2 large projects annually to 610 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 organizations delivery capabilities.

Salary range: $110000.00 - $125000.00 CAD per year