Director of Professional Services

Project Portfolio ManagementDefine 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 & AdoptionTreat 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 GrowthIdentify 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 OwnershipOwn 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 & ScalingDesign 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 ContributionMentor 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 Apply To This Job