Senior Project Manager (Planning & Permitting System Implementation) to support Transformation Office within Public Sector 1-year contract | Hybrid (2-3 days onsite at 71 Main St. W)

Possibility of extension

35 Hrs/Week

Summary Seeking an experienced

Senior Project Manager

to lead the implementation of a new enterprise Planning, Permitting, Licensing, and Bylaw system ( POSSE ). This is a critical, high-visibility, customer-facing project replacing the former Amanda platform.

The new online portal will enable citizens to submit building permits, apply for licenses, make updates, and interact digitally with City services. This role requires a PM who can drive delivery, manage complex technical implementations, coordinate cross-functional resources, and ensure strong communication across all stakeholder groups.

This project is currently at a

critical stage , approaching a major go-live in early March, with multiple waves of enhancements to follow. The successful PM will step in quickly, organize workstreams, keep people aligned, and lead the project through implementation, stabilization, and subsequent releases.

Key Responsibilities (D2D)

Lead the end-to-end delivery of the new

POSSE

planning & permitting system.

Coordinate and direct work across business units, IT, vendors, and project team members (without direct authority).

Ensure schedules, deliverables, risks, decisions, and issues are clearly documented, communicated, and actioned.

Manage technical project components - must be comfortable understanding software, integrations, and implementation considerations.





Oversee change management activities for a large user group that has been heavily impacted and is undergoing major process changes.

Ensure all project members (business analysts, change specialist, IT team, Product Owner) stay aligned and on track.

Drive structured planning, follow-up, execution, and issue resolution.

Support an out-of-the-box system implementation approach (low-customization).

Maintain strong communication across a complex environment with many moving parts.

Build strong relationships in a predominantly in-office project team environment.

Support ongoing enhancements and future phases after initial launch.

Must-Have Qualifications

Strong Senior PM experience

leading major software implementation projects.

Experience with

planning, permitting, licensing, or building systems

(e.g., Amanda, POSSE, or similar municipal systems).

Ability to understand

building permit complexities , development workflows, inspections, approvals, etc.

Strong technical acumen - must understand software system dependencies, integrations, constraints, and implementation considerations.

Excellent communication skills - explicit, proactive, structured, and able to align multiple stakeholder groups.

Experience leading cross-functional teams

without formal authority .





Exceptional organizational and planning skills; ability to drive follow-up and keep the project moving.

Proven ability to manage large-scale municipal or regulatory technology projects.

Demonstrated strength in change management for user groups undergoing significant transition.

Ability to work onsite

2-3 days per week

(team is in office most days).

Experience with the

Amanda

system or direct business knowledge of Planning & Building operations.

Previous work in municipal government or regulatory environments.

Experience with customer-facing online portals.

Familiarity with out-of-box, configuration-based implementations (vs heavy customization).

Experience working on systems within cyber-impacted recovery contexts.

Ability to quickly build trust with a group that has been through the ringer and is navigating large process shifts.

Location: Hamilton, ON

Nice-to-Have / Plusses

Experience with the

Amanda

system or direct business knowledge of Planning & Building operations.

Previous work in municipal government or regulatory environments.

Experience with customer-facing online portals.

Familiarity with out-of-box, configuration-based implementations (vs heavy customization).

Experience working on systems within cyber-impacted recovery contexts.

Ability to quickly build trust with a group that has been through the ringer and is navigating large process shifts

Disclaimer: AI may be used in evaluating candidates.

This posting is for an existing vacancy.

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📌 Senior Project Manager (Planning & Permitting System Implementation) to support Transformation Offic (Winnipeg)
🏢 S.I. Systems
📍 Winnipeg