About The Career Foundation:

The Career Foundation is a dynamic non-profit organization and registered charity that offers a wide range of employment, training, and workforce development services to job seekers and employers. Since its inception in 1988, The Career Foundation has steadily expanded its services. Operating out of seven locations in the Greater Toronto Hamilton Area, as well as  offices in British Columbia, Alberta, and Nova Scotia, we now help thousands of people each year successfully achieve their employment goals. Our team of dedicated professionals has described The Career Foundation as caring, compassionate, innovative, and team-oriented. For more information about us and our services, please visit our website at CareerFoundation.com.

Some of the benefits and features available to our employees include: 

• Competitive compensation
• A comprehensive health benefits plan that includes massage therapy, naturopath services, travel coverage, and much more
• A comprehensive dental insurance plan
• An RRSP Matching benefit
• An Employee & Family Assistance program
• Employee wellness initiatives
• Paid days off for religious observance purposes
• Paid days off for personal wellness purposes

Role Description:

In this executive-level role, the Senior Officer, Strategy and Organizational Effectiveness will work closely with The Career Foundation’s CEO in shaping the organization’s future and delivering on its strategic vision. The ideal candidate is a dynamic, proactive, and forward-thinking leader and doer who turns vision into action, anticipates challenges, removes roadblocks, and aligns teams to achieve organizational goals through clear communication, collaboration, decisive action, and strong execution.

The successful candidate brings proven strategic thinking, problem-solving skills, and adaptability, combined with excellent communication, rapport-building, and emotional intelligence to foster alignment and drive successful execution of goals.

As a catalyst for organizational effectiveness, the incumbent will ensure that strategic priorities are executed with precision, organizational performance is optimized, and communication flows seamlessly across all levels of the organization and among various stakeholders. The successful candidate will have the ability to influence a culture that values innovation, collaboration, and impact.

Position Type:

Full-time (37.5 hours per week)

Base Location and Travel Requirements:

The position’s official base location is The Career Foundation’s Head Office at Lawrence Avenue West and Allen Road in North York. As a member of the executive team, the Senior Officer, Strategy and Organizational Effectiveness will also travel to other company locations within the Greater Toronto and Hamilton Area (GTHA), partner sites, and stakeholder locations to fulfill the scope of the position.

The successful candidate should possess a valid Ontario G driver’s licence and a vehicle for frequent travel between locations and other stakeholder sites across the GTHA.

The role will also permit a hybrid-remote work schedule, as approved by the CEO and contingent on scope of work. The hybrid schedule requires a private work-from-home space with reliable high-speed internet. A company laptop, cell phone, and other equipment will be provided.

Vulnerable Sector Check Requirement:

An offer of employment for this opportunity will be contingent on the incumbent providing an acceptable Vulnerable Sector Check (VSC).

Start Date:

As soon as possible

Reporting to:

Chief Executive Officer (CEO)

Experience level required:

7+ years

Responsibilities include:

 Strategic Planning and Execution

• Collaborates with the CEO to define, prioritize, and execute strategic initiatives, leading high-priority cross-functional projects from conception through delivery and ensuring all measurable outcomes are achieved.
• Establishes performance dashboards on organizational health indicators to track and measure progress against organizational goals and KPIs outlined in the strategic plan.
• Translates high-level strategy into actionable roadmaps with clear milestones and ownership.
• Applies appropriate management and business operation methodologies, tools, and skills to develop detailed work plans, instill rigor, and drive end-to-end execution.
• Supports the preparation of annual and quarterly strategic planning sessions, executive and manager meetings, and town hall events.
• Identifies new opportunities to advance the mission and strengthen impact, contributing to the organization’s long-term vision and direction.
• Designs multi-year, cross-program strategies, roadmaps, and success measures that ensure alignment with community needs, funder expectations, and organizational priorities.
• Resolves high-priority strategic challenges such as program growth and sustainability, change management, organizational redesign, and ad-hoc initiatives requiring executive-level attention.
• Ensures solutions are mission-aligned, financially responsible, and responsive to stakeholders.

Organizational Effectiveness

• Assesses and streamlines workflows, processes, and systems to enhance efficiency and productivity.
• Reviews and redesigns organizational structures to address gaps and strengthen capabilities.
• Conducts organizational health assessments to monitor engagement, morale, and overall effectiveness.
• Leads organization-wide changes and develops new processes and capabilities to support evolving operational needs in a nonprofit environment.
• Drives a culture of continuous improvement and operational excellence.
• Supports talent development programs to build leadership capacity and future-ready skills.
• Establishes governance frameworks that clarify decision-making authority and accountability.
• Designs and manages planning and coordination mechanisms, monitoring program and organizational performance metrics to establish and drive the operating rhythm of the organization.

CEO and Executive Team Support

• Serves as a strategic partner to the CEO and collaborates with the executive team on growth initiatives.
• Acts as the communication bridge between the CEO, Board of Directors, and other internal/external stakeholders.
• Translates vision into reality by bridging the gap between high-level strategy and day-to-day operations.
• Proactively identifies and solves problems, enabling leaders to focus on other priorities.
• Drives alignment by ensuring teams understand and are motivated to work toward shared goals.
• Acts as a trusted extension of the leadership team, handling critical tasks with discretion.
• Oversees preparation for executive and board meetings, including agendas, briefing materials, and follow-up actions.
• Drafts reports, presentations, and communications articulating strategy, progress, and impact.
• Coordinates solution-focused executive-level offsite planning events to ensure collaboration and alignment on priorities.
• Manages executive workflows and decision calendars, ensuring timely follow-through on commitments.
• Develops stakeholder engagement strategies to strengthen relationships with key partners, funders, and regulators.

Special Projects and Initiatives

• Leads and drives execution of strategic initiatives with end-to-end ownership, including identifying priorities, developing actionable plans, convening cross-functional teams, and managing progress, risks, and dependencies.
• Supports the CEO with ad-hoc initiatives such as market analysis, partnership development, and innovation opportunities.
• Pilots new initiatives or programs, testing feasibility before scaling organization-wide.
• Evaluates new funding strategies or earned revenue opportunities and assesses compliance with charitable and nonprofit laws and requirements.
• Designs scenario planning models to prepare the organization for future risks and opportunities.
• Ensures initiatives are delivered on time, within budget, and with measurable outcomes that advance the nonprofit’s mission.
• Performs other relevant assignments as needed.

Qualifications/ Skills Required:

• An advanced degree, such as an MBA, is highly preferred, with a minimum of 7+ years of senior-level experience in a role focused on organizational effectiveness, organizational design, process improvement, change management, and project management, including planning, leading, and executing strategic initiatives.
• Successful track record of leading cross-functional initiatives and delivering measurable impact.
• Knowledge of the Employment Services industry and the Workforce Development landscape, including challenges faced by job seekers, is considered an asset.
• Strategic thinking and foresight: able to see the big picture, anticipate future trends, and make decisions that balance short-term needs with long-term goals.
• Strong analytical skills with the ability to translate data into actionable insights and clear work plans.
• Capacity to identify problems, analyze data, and develop effective solutions.
• Experience designing scenario planning models and managing multiple, competing priorities efficiently.
• Influential leadership capabilities with the ability to align people and resources with objectives and build relationships across teams.
• High emotional intelligence: demonstrates empathy, builds trust, and understands diverse perspectives.
• Adaptable and resilient, able to navigate ambiguity and dynamically changing priorities in a fast-paced environment.
• Ability to serve as a trusted advisor and handle sensitive information with the utmost confidentiality and discretion.
• Exceptional communication skills, including advanced written and verbal English proficiency, polished presentation and public speaking abilities, and the capacity to communicate with clarity, listen actively, and adapt style to diverse audiences. Bilingualism in French or another language is considered an asset.
• Skilled at influencing senior stakeholders and aligning teams toward shared objectives.
• Advanced proficiency in Microsoft Office, Adobe Suite, and Office 365 (including MS Teams and SharePoint).
• Tech-savvy with experience using, or the ability to quickly learn, other systems and software such as MailChimp, WordPress, Power BI, Canva, and project management tools.
• Strong detail orientation for developing and maintaining data tracking systems.
• Excellent project and time management skills with the ability to multi-task and meet deadlines.
• Process- and people-oriented with clear, respectful communication skills and the ability to build trust and rapport across all stakeholder groups.
• Professional and courteous approach to client service, demonstrating exceptional customer service skills, a strong commitment to upholding the organization’s core values, and a high level of respect for diversity.
• High ethical standards and confidentiality, consistently exhibiting tact, diplomacy, and sound judgment.
• Willingness and flexibility to occasionally work outside regular business hours for critical meetings and engagements.
• Proactive and solutions-oriented leader who takes initiative, anticipates needs, and owns outcomes, while fostering a positive team culture, demonstrating accountability, and driving collaboration and shared success.

The Career Foundation’s Commitment:

The Career Foundation is committed to diversity and inclusion and aims to create a healthy and rewarding environment for all. We welcome applications from qualified individuals who represent the diversity of the people we proudly serve, including, but not limited to, visible minorities, women, persons with disabilities, Indigenous peoples, and individuals of all genders and sexual orientation. The Career Foundation, in accordance with the Accessibility for Ontarians with Disabilities Act (AODA), is also committed to accommodating applicants with disabilities throughout the recruitment process. We will work with candidates requesting accommodation at any stage of the hiring process.