Director, Employment Services

Director Employment & Social Enterprise

The Agency

The Calgary John Howard Society (CJHS) is a charity that reduces crime and makes Calgary communities safer by helping youth and adults make positive changes and move away from criminal behaviour. We do this by addressing the root causes of crime through housing, education, employment programs and support so that individuals have alternatives to breaking the law. CJHS is committed to restorative justice and an organizational environment that recognizes the dignity and worth of each person. CJHS values diversity and inclusion and welcomes qualified applicants from all walks of life.

Position Title: Director, Employment & Social Enterprise

Reports to: Executive Director

Location: On-site

Status: Full-Time, Permanent

Position Summary

We are seeking a visionary and results-driven
Director of Employment & Social Enterprise
to lead the creation, launch, and ongoing success of the
Reintegration Employment Hub
—a multi-million-dollar initiative supporting adults with justice involvement and complex barriers as they reintegrate into society through meaningful, long-term employment.

This senior leadership role offers a rare opportunity to architect a comprehensive program from inception—shaping its strategic direction, driving daily operations, and cultivating a culture of excellence, innovation, and impact.

The successful candidate will combine strong business acumen with an entrepreneurial mindset and a proven ability to deliver complex projects. They will build a high-performing team, implement scalable systems and performance metrics, and foster cross-sector partnerships to generate sustainable employment pathways. This leader will also play an integral role in organizational strategy, aligning the Hub with CJHS's broader mission and goals.

Key Responsibilities

Employment Program Design & Implementation

• Lead the design and launch of the Reintegration Employment Hub, including scalable service delivery models and wraparound supports (e.g., occupational therapy, digital literacy, financial coaching).
• Establish performance metrics and ensure continuous quality improvement through data-driven decision-making.
• Build and refine program policies, procedures, and workflows to ensure accountability, efficiency, and positive participant outcomes.

Social Enterprise Leadership

• Provide strategic oversight of CJHS's social enterprise construction company, a multi-agency collaborative offering hands-on training and employment for justice-involved participants.
• Oversee day-to-day operations including project planning, bidding, estimating, job costing, safety compliance, and quality control.
• Develop financial sustainability models, including budgets, forecasts, and revenue targets that balance profitability with social mission.
• Build partnerships with agencies, trade associations, and industry experts to ensure accountability and strong collaboration.
• Secure new business opportunities and contracts with private, public, and non-profit partners.
• Explore new service lines, social procurement opportunities, and green construction initiatives aligned with community and sustainability priorities.
• Implement performance measurement systems to track social, economic, and training outcomes.
• Ensure operations reflect trauma-informed and inclusive employment practices.

Team Leadership & Culture Building

• Mentor and inspire a multidisciplinary team, fostering professional growth and a trauma-informed, equity-focused culture.
• Model compassionate accountability and innovation, ensuring staff feel empowered to deliver outcomes-based results.
• Commit to personal and professional growth through reflective practice and self-leadership.
• Commit to full participation and support of a high-performing leadership team built on trust, candor, accountability, and relationship.

Employer Engagement & Partnerships

• Build and maintain relationships with employers across multiple sectors (construction, trades, hospitality, retail, etc.) to create sustainable employment pathways.
• Convene employer partners to co-design training pipelines, reduce recruitment risks, and normalize inclusive hiring practices.
• Collaborate with industry associations, government agencies, and community organizations to expand opportunities and strengthen regional impact.

Financial & Operational Stewardship

• Oversee a multi-million-dollar budget, ensuring optimal resource allocation and compliance with funder requirements.
• Manage a performance-based funding model, aligning financial planning with program targets and organizational sustainability.
• Prepare and deliver timely, accurate reports to funders and the CJHS executive team.

Organizational Strategy & Integration

• Collaborate with the Executive Director and leadership team to align the Hub with CJHS's broader strategic priorities.
• Contribute to organizational decision-making, growth planning, and cross-program collaboration to maximize impact.

Innovation & Continuous Improvement

• Stay informed on employment and social enterprise trends, justice-system reforms, and employer needs.
• Pilot innovative approaches to strengthen job retention and participant success.

Qualifications

• Experience
  :
• Minimum 7–10 years of progressive leadership experience, ideally within business, social enterprise, workforce development, or related sectors.
• Proven track record in launching and scaling complex initiatives.
• Demonstrated experience in budget oversight, financial forecasting, and performance-based funding models.
• Education
  : A post-secondary degree in business, social sciences, public administration, or a related field. Equivalent experience will also be considered.
• Skills & Competencies
  :
• Strong business acumen with an entrepreneurial approach to problem-solving.
• Exceptional relationship-building and partnership development skills.
• Experience leading multidisciplinary teams with a focus on trauma-informed and equity-based practices.
• Strong communication and presentation skills; comfortable engaging funders, employers, and community stakeholders.
• Knowledge of justice-related issues and systemic barriers faced by individuals with criminal records is an asset.
• Ability to balance strategic thinking with hands-on operational leadership.

Additional Information

Your past does not define your future. A criminal record will not disqualify you from employment with us; each application is evaluated individually.

Applications will be accepted until October 25, 2025.

Please submit your cover letter and resume to:

The Calgary John Howard Society thanks all applicants; however, only those

considered for an interview will be contacted.