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 monthsLead PS team members in the execution projects and perform direct customer‑facing project management duties as requiredEnsure successful project delivery aligned with revenue targets and client satisfactionManage remote, cross‑functional teams of Application Consultants, technical specialists, and SMEs across all product linesApply 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 leadersAI 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 closeoutLeverage AI tools to scale implementation capacity, enabling a small PS team to support a growing number of large, complex projects without linear headcount growthContinuously evaluate and implement AI tools that accelerate project planning, automate documentation generation, and improve cross‑project visibilityRevenue Expansion & Customer GrowthIdentify and act on organic revenue expansion opportunities within the existing customer base, including additional implementation phases, training, consulting, and scope extensionsCollaborate with Sales and Account Management to surface PS opportunities arising from customer interactions, implementation milestones, and product upgradesSupport late‑stage recent‑name sales opportunities by contributing detailed implementation plans, realistic timelines,



and credible PS scoping to proposals and RFP responsesEnsure methodology investments on early large‑scale implementations are packaged to accelerate delivery and PS revenue realization on subsequent projects of similar scopeFinancial OwnershipOwn the Professional Services P&L across HHES and SDS, with accountability for sustaining a revenue‑to‑expense ratio of 2xMaintain rigorous monthly revenue forecasts based on scheduled project work, backlog, milestone billings, and in‑month sales activityManage percent‑complete (EAC) revenue recognition with accuracy, ensuring WIP balances are actively managed and forecasts reflect true project progressEnsure compliance with revenue recognition standards, including IFRS, across both simple and complex engagementsDesign project invoicing milestones that maintain healthy working capital across AR and WIPTrack and report KPIs including PS Ratio, utilization, effective hourly rate, and forecast accuracyProcess Development & ScalingDesign scalable delivery frameworks, tracking tools, and standardized documentation for each product line, building on the organization’s existing AI‑generated template assetsDevelop methodology explicitly designed to scale implementation volume from approximately 2 large projects annually to 6–10, within the current team structureCreate commercially sound, operationally realistic Statements of Work and formal project documentation for both customer‑facing and internal/sales purposesTeam Leadership & Strategic ContributionMentor and support a team of Application Consultants with AI fluency as an explicit and measurable component of performance expectationsSet clear performance standards, conduct regular evaluations, and own PS team recruitingServe as a key member of the business unit leadership team, contributing to tactical and strategic planning across SDS and HHESSupport Sales and Marketing through RFP responses, implementation methodology documentation,



and go‑to‑market materials that differentiate the organization’s delivery capabilitiesQualificationsProven experience leading complex software implementation projects in ERP, Point‑of‑Sale, Student Information Systems, or comparable vertical market software domainsDemonstrated success in building and scaling PS delivery processes from the ground up in a small‑team, high‑growth environmentStrong financial management capability, including hands‑on experience with percent‑complete (EAC) revenue recognition, PS P&L ownership, WIP management, and revenue forecastingDemonstrated comfort operating a PS team at a revenue‑to‑operating‑expense ratio of 2x or greaterConcrete, 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 visionExperience managing remote, cross‑functional teams with accountability across distributed environmentsServant‑leader with the ability to apply structured methodologies internally while remaining approachable and relationship‑centered with K‑12 and higher education customersResults‑driven, capable of defining relevant KPIs and milestones, then measuring progress to achieve long‑term goalsPreferred QualificationsVertical market software experience; Education technology (K‑12 and/or higher‑education) considered a strong assetFamiliarity with IFRS revenue recognition policiesExperience with project tracking tools (e.G., Jira, Smartsheet, MS Project)Degree in Business Administration or Finance/Accounting, or equivalent operational experiencePMP or equivalent certification, applied with the flexibility appropriate to an education‑sector customer baseApply AI to extract insight from project data — identifying delivery patterns, risk indicators, and customer engagement trends that inform operational and revenue decisionsLead change management efforts to embed AI into team workflows, with measurable adoption expectations and AI fluency as an explicit component of team performanceSalarySalary range: $110,000.00 – $125,000.00 CAD per year#J-18808-Ljbffr

📌 Director Of Professional Services - C$110,000 - C$125,000 A Year - Remote (Winnipeg)
🏢 N. Harris Computer Corporation - CAD
📍 Winnipeg