Program Manager Jobs in Pickering, ON (NOW HIRING)

Join Our Team and What We'll Accomplish Together

We are seeking a Senior Program Manager to drive business integration, strategic program execution, and organizational stability across the Employer organization. This is a pivotal moment for our team-we're integrating acquired companies, scaling operations, and building a data-driven operating model. You'll be the architect of clarity and accountability during this period of growth, ensuring our highest-priority initiatives deliver measurable outcomes and the organization operates with focus, speed, and accountability.

This role sits at the center of leadership priorities and execution realities. You'll translate shifting strategic directives into clear, actionable plans; drive consistent execution across cross-functional teams; and help stabilize the organization by bringing structure to ambiguity and reinforcing a culture of accountability and data-driven decision-making.

What You'll Do

Leadership Operating Cadence & Performance Governance

Own end-to-end preparation and execution of the bi-weekly Sales Performance operating cadence (SVP/VP level), consolidating inputs across Sales, Finance, and Operations. Partner with key stakeholders to validate data, identify risks and gaps ahead of each meeting, and translate meeting outputs into actionable initiatives with clear ownership and progress tracking. Serve as the central point of coordination for Employer KPIs, partnering with leaders across Sales, Finance, and Operations to define KPI standards, track performance against targets, and maintain a clear view of organizational health and progress.

Strategic Initiative Leadership & Execution

Directly lead execution of high-priority, cross-functional initiatives including: Fee-for-Service Sales Performance & Compensation (stand up consistent reporting and align compensation structures); Consolidated Reporting Across Employer Acquisitions (partner with BI to create unified reporting across acquired entities); Time-to-Value Acceleration (redesign client implementation processes to reduce onboarding bottlenecks); and Reseller Forecasting Enhancement (improve forecasting accuracy and align inputs across Sales and CSM teams). Manage program-level tracking for all active initiatives-timelines, milestones, risks, dependencies-and proactively identify and remove blockers to maintain momentum.

Driving Focus, Clarity & Accountability

Eliminate organizational "noise" by clarifying priorities and removing low-value or duplicative work. Hold cross-functional stakeholders accountable to commitments and outcomes. Provide regular, structured updates to leadership on progress, risks, and results. Help teams execute without ambiguity or unnecessary friction.

Translating Vision to Action

Translate leadership priorities into actionable plans with defined initiatives, clear timelines, and identified owners. Work with leadership to identify and resolve areas of friction during integrations or organizational change. Bring structure and visibility to fast-moving environments where priorities shift, ensuring teams stay aligned and execution remains consistent.

What You Bring

Program Leadership & Execution

• 3+ years leading cross-functional programs/initiatives (integrations, organizational restructures, platform launches, or similar) where you drove outcomes beyond your direct control
• Demonstrated ability to manage multiple concurrent programs at the program level, translate strategy into execution, and deliver measurable results
• Strong ability to manage dependencies, identify risks early, and drive resolution proactively
• Business Acumen & Data-Driven Decision Making
• Strong analytical and problem-solving skills with a demonstrated track record of using data to inform decisions and track program success
• Experience building KPI frameworks, defining success metrics, and using performance data to course-correct initiatives
• Ability to translate business metrics into clear narratives for leadership

Leadership & Stakeholder Influence

• Demonstrated ability to influence and drive accountability at senior levels (director and above) without direct authority
• Comfortable engaging and challenging senior stakeholders; comfortable operating with ambiguity and being challenged by strong personalities
• Clear and concise communicator with ability to ask clarifying questions, identify misaligned priorities, and drive alignment without creating friction

Organizational Effectiveness

• Ability to bring structure to ambiguity and drive clarity in fast-moving environments
• Experience navigating organizational politics and understanding cultural nuances within complex organizations
• Proven ability to identify what can and cannot change in a given context, and adjust approach accordingly

Preferred Qualifications

• Experience supporting business integrations, reorganizations, or scale-up environments
• Familiarity with sales operations, performance management, or operational finance

Why This Role Matters

By driving alignment, reducing friction, and enabling consistent execution, you help the business operate with focus, speed, and accountability. This role focuses on organizational execution, integration, and performance management-ensuring the organization's highest-priority initiatives are executed effectively and deliver measurable outcomes.

Key Responsibilities Include:

• Build and manage business integration plans with clear milestones, ownership, and success metrics
• Support and maintain leadership operating cadence and governance forums
• Partner with Finance, Sales, and Operations to define, track, and improve KPI performance
• Lead 4-5 concurrent strategic initiatives from conception to completion
• Identify and resolve organizational friction points and dependencies