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