City of Winnipeg

Lead the working-level integration of a multi-year program with one objective: keep fare collection operating while defining, funding, procuring and preparing the organization for a modern successor capability. The program connects legacy continuity; fare policy, Concept of Operations, business case and capital-path work; a multi-stage negotiated RFP; implementation and transition readiness; and future business readiness and operating-model maturity.

I manage dependencies and controlled handoffs across Transit operations, technology, Purchasing, Legal, Finance, consultants and senior stakeholders. Future implementation, migration and decommissioning are roadmap scope and are not presented as completed work.

Led delivery of a $1.3M shared SaaS platform that replaced separate booking and scheduling platforms for Winnipeg Transit Plus paratransit and On-Request service. It added web and mobile self-service alongside telephone booking, real-time scheduling and dispatch, and a foundation for coordinating door-to-door paratransit and zone-based on-request service.

After award, as PRINCE2 Senior Supplier, I completed the contract and SOW with Legal, established the budget, hired the Project Manager, and directed the PM, technical lead and analysts through cloud architecture, privacy assessment, data migration, testing, training, cutover and transition to operations. Since the June 2024 launch, on-time performance reached 97.18% against a 92-95% target and customer satisfaction reached 91.96% against a 75-84% target; self-service and automated workflows also reduced manual work.

I currently lead a roughly two-year acquisition of a new enterprise commercial platform as the City's point of contact and Contract Administrator for RFP 965-2025. The requirements-definition phase alone took six months. With consultant support, I turned evidence from the current platform, the approved fare direction and Concept of Operations, and two rounds of discovery and validation across eight City functions into outcome-based business objectives, detailed capabilities and conditions for award.

I have carried the six-stage process through the vendor conference, preliminary screening and detailed technical proposals; coordinated responses to extensive technical RFIs and the current evaluation; and am preparing governed demonstration scenarios ahead of pricing and negotiation.

As the City's Consulting Contract Administrator, took RFP 445-2024 from a broad need to an approved consulting engagement. Work began in February 2024. I drafted its three-tier analysis across nine public-service and policy lenses, then aligned four managers through several review cycles around a jointly approved scope. The RFP was published in May and the consulting contract was executed in September 2024. The mandate covered the current state, Canadian and international peers, future technology, implementation, Class 3 costs and senior-management and Council deliverables.

I administered the engagement through discovery, analysis, the Concept of Operations, requirements baseline and business-case inputs. The resulting work entered the public Council process in March 2025. The head of the function authored and advanced the administrative report through executive and political review; in May 2025 Council approved the Class 3 estimates and an additional $4M, bringing the capital budget to $10.5M and completing the fare-policy mandate. The approved work now underpins RFP 965-2025.

Led a three-year continuity and renewal program for the existing fare platform from February 2023 to December 2025 while its replacement pathway advanced. Coordinated phased upgrades and migrations across about 35 production and development servers, including both database environments.

Each move was governed as a small cutover project: dependency and risk review, change approval, vendor and City-team coordination, testing and rollback plans, business validation, production acceptance and decommissioning. The platform continued serving riders throughout the sequence. When a critical subcontractor intended to withdraw support for a legacy component, I negotiated a special extension through the primary supplier to keep it supportable until migration. I also established recurring governance for production performance, service issues and lifecycle decisions, and carried the resulting constraints into replacement planning and procurement.

Inherited an underfunded effort to replace a legacy application controlling serialized paper tickets and passes distributed through retail consignment and bulk sales. Reset the work around a fresh business case and capital-funding need, then led validated user stories, requirements, functional designs and traceability across ordering, warehouses, serial numbers, commissions, returns and finance.

Prototyped two commercial inventory products but rejected them when serial-number control and per-location cost did not fit. Redirected the solution into PeopleSoft Order Management, producing process flows, configuration analysis, functional specifications and test planning before delivery was suspended because funding could not support the required analyst capacity. The validated baseline now supports a controlled investigation of AI-assisted custom development, subject to City security, privacy, implementation ownership and support requirements.