Chief Operating Officer Remote Jobs in Ontario (NOW HIRING)

Title: Chief Technology Officer

Department: Technology

Reporting to: Chief Business Officer

Location: Remote - Canada (Candidates based in British Columbia, Alberta, Manitoba, Saskatchewan, Ontario, Nova Scotia, or willing to relocate)

Compensation: $220K - $250K CAD

Who We Are: 

World Education Services (WES) is a non-profit social enterprise that supports the educational, economic, and social inclusion of immigrants, refugees, and international students. For 50 years, WES has set the standard for international academic credential evaluation, supporting millions of people as they seek to achieve their academic and professional goals. Through decades of experience as a leader in global education, WES has developed a wide range of tools to pursue social impact at scale. From evaluating academic credentials to shaping policy, designing programs, and providing philanthropic funding, we partner with a diverse set of organizations, leaders, and networks to uplift individuals and drive systems change. Together with its partners, WES enables people to learn, work, and thrive in new places. For more information about WES, please visit our website at www.WES.org.    

About The Opportunity: 

WES is seeking a Chief Technology Officer (CTO) to provide technical and strategic leadership for the Technology organization which operates as a distributed team across the US, Canada and India. The CTO is responsible for defining and delivering the technology strategy that aligns with organizational goals and strategic ambitions, supporting current operations and growth plans. The CTO accelerates digital innovation, including driving the implementation of digital transformation programs.

Reporting to the Chief Business Officer (CBO), the CTO sets the enterprise technology vision and drives execution—balancing organizational priorities, risk, budget, and emerging technology trends to deliver secure, scalable, effective, and strategically focused technology infrastructure and capabilities.

This is an exciting opportunity to lead and inspire a talented technology team at a mission driven social enterprise, shaping WES’s technological future and partnering across the organization to drive digital transformation.

Success in this role looks like (6–12 months):

• A pragmatic 12–24-month technology roadmap is established and aligned to organizational priorities, with clear sequencing, ownership, milestones, and measurable outcomes.
• Core platforms, systems and infrastructure meet defined reliability and performance targets, with improved incident response and service delivery practices.
• Technology and Product partnership models are strengthened, enabling more effective prioritization, cross-functional alignment, and delivery of business-critical activities.
• Security, risk, and audit readiness are strengthened through documented controls, regular testing, and an actionable remediation plan.
• A scalable operating model is in place (roles, governance, vendor management, and delivery rhythms) and the Technology team is engaged and developing.
• Key cross-functional initiatives show measurable progress (e.g., modernization, automation, analytics enablement) with stakeholder confidence and adoption.

What You'll Do:

Technology Strategy & Vision

• Lead the development and execution of WES’s technology strategy and operating model in alignment with organizational priorities and 3-year strategic plan, partnering closely with the Product department and leadership across WES to deliver scalable, reliable and business-aligned technology capabilities.
• Partner with the executive team to define and advance WES’s AI vision, strategy and priorities in support of opportunities to create organizational value, accelerate innovation, and strengthen mission impact.
• Lead the development of a responsible AI operating model, including governance, risk management, compliance, security, privacy, and ethical oversight to enable trusted and scalable adoption.
• Define and evolve a scalable, interoperable enterprise technology ecosystems across commercial, and enterprise platforms.
• Drive simplification and rationalization of systems, workflows, integrations, and vendor footprint to reduce operational complexity and improve scalability.
• Identify and evaluate the latest technologies, assessing their potential for strategic advantage and organizational impact.
• Define and execute clear initiatives, programs, and priorities tailored to the organization’s strategic objectives and mindful of business needs, growth ambitions, and requirements related to scale and operational efficiency.
• Develop internal innovation rooted on emerging technologies and industry trends, including AI, automation, workflow orchestration, and modern data architectures. Identify, and pragmatically apply the solutions that make the most impact within the WES context.

Technology Organization Leadership & Transformation

• Design and lead the evolution of the Technology organization; build the operating model, talent, and capabilities needed to achieve technology goals in line with our strategic plan and business needs.
• Establish disciplined portfolio and resource planning practices that balance delivery velocity, operational stability, team capacity, and financial stewardship.
• Define the enterprise AI architecture, platforms and enabling infrastructure required to scale AI capabilities at WES securely, reliably and in alignment with business needs.
• Build and lead a high-performing Technology team, fostering a culture of collaboration and continuous growth and learning through coaching, mentorship, feedback, and professional development so leaders and their teams can excel.
• Oversee the design and implementation of robust technical architectures, ensuring alignment with business requirements, security standards, and industry best practices.
• Establish and maintain efficient, reliable, and scalable technology operations across systems, infrastructure, and networks, with clear service management practices (e.g., incident management, change management, monitoring).
• Strengthen data and analytics capabilities (governance, quality, tooling, and reporting) to provide timely, trusted insights that support decision-making and organizational growth.
• Lead security, risk, and resilience services, including information security, audit readiness, risk management, disaster recovery, and business continuity—ensuring controls are documented, tested, and continuously improved.
• Identify—and where appropriate, accelerate—innovative initiatives to enhance technology processes, systems, and services for optimum efficiency.

Business Partnership, Program Delivery & Governance

• Partner with executive and senior leadership across the enterprise to understand their technology needs and translate business strategy into technology priorities, technology-enabled initiatives and measurable outcomes.
• Partner with executive and department leaders to build enterprise readiness for AI adoption through workforce upskilling, capability building, change enablement and a culture of experimentation, learning and responsible use.
• Lead the execution of technology programs and projects in partnership with cross-functional teams and stakeholders—ensuring scope, timeline, quality, and adoption.
• Establish clear priorities and transparent operating rhythms (planning, governance, metrics) to deliver against strategic needs.
• Evaluate and recommend technology solutions to address business challenges, improve user experience, and increase operational efficiency.
• Engage with the Board to communicate technology strategy, investments, progress, and key risks.

Vendor & Financial Management

• Manage relationships with technology vendors and partners, evaluating and selecting the most suitable services and solutions and ensuring these deliver best value, service and outcomes for WES.
• Create and manage the technology budget, optimizing resource allocation, ensuring appropriate investment in appropriate, future-fit platforms or technologies and ensuring strong financial stewardship, ROI and cost-effectiveness.

Your Experience:

Required

• 10+ years of experience leading or managing technology functions, with progressive responsibility, including prior CTO level experience.
• Bachelor’s degree in computer science, engineering, or a related field (or equivalent experience).
• Proven experience leading distributed and/or remote teams.
• Experience operating in complex, evolving organizations with multiple products, services, stakeholder groups, or business capabilities.
• Strong knowledge of modern technology capabilities and trends; demonstrated ability to use this knowledge for strategic decision-making.
• Demonstrated success leading complex transformation initiatives (process, systems, and operating model).
• Strong commitment to the WES mission and values.
• Highly collaborative leadership style with the presence and influence to align stakeholders and deliver technology outcomes that support WES’s strategic goals.
• Excellent interpersonal and communication skills.
• Ability to develop constructive, effective working relationships at all levels of the organization.
• Entrepreneurial mindset with high drive, ownership, and strong work ethic.
• Demonstrated ability to build a culture of innovation, experimentation, and continuous improvement.
• Willingness and ability to travel domestically and internationally, as needed, to support global operations, partner engagement, team leadership and industry conferences/events.

Desired

• Master’s degree in computer science, engineering, or business administration preferred (or additional directly related experience).

What We Offer:

Joining our team at WES means embarking on a purpose-driven career with a global impact, where you contribute daily to making a tangible difference in the lives of people worldwide. You'll thrive in an employee-centric environment, with access to learning opportunities, pathways for personal and professional development, and recognition of your achievements. Our inclusive, mission-driven culture values employees and focuses on investing in our people through our culture, people framework, and programming while offering the flexibility of remote work options.

• Work-Life Harmony: We believe that success is all about maintaining balance. Enjoy the freedom of remote work and flexible scheduling, paired with generous time-off policies designed to assist you in maintaining a healthy equilibrium between your personal and professional commitments. Our comprehensive wellness programs and work environment are focused on fostering your well-being.
• Rewards and Recognition: Your dedication and achievements are the cornerstone of our success. We recognize the importance of valuing your hard work, which is why we offer competitive compensation, comprehensive benefits, and tangible rewards to celebrate your contributions.
• Professional Growth and Development: We are committed to nurturing growth within our team, recognizing that growth is essential to providing opportunities for career advancement and ongoing professional development. To prioritize your learning and success, we invest in comprehensive training programs and offer tuition reimbursement opportunities. We promote a culture of continuous learning that empowers you to thrive and evolve in your career.
• Innovation and Impact: Engage in work that directly transforms lives and empowers individuals and communities by expanding access to global educational and professional pathways. Join us in fostering a culture that values innovation, embraces new approaches, and leverages transformation to implement and drive impactful change.
• Community and Connection: Our team is made up of individuals from different cultures and backgrounds who have varying perspectives and ideas. Our diverse workforce reflects the global community we serve, and we take pride in it. We are committed to fostering a workplace where everyone feels valued, respected, and included. Experience the power of connection by participating in a range of activities, including employee-led resource groups, town halls, collaborative team events, meaningful volunteer opportunities, and initiatives that promote equity, celebrate diversity, and cultivate a strong sense of belonging within our organization.

  Values:

• Opportunity - We open doors so people can build better futures.
• Inclusion - We become stronger, more creative, and more resilient when we embrace diversity.
• Equity - We uphold fairness and justice in our work and actions.
• Enterprising - We are resourceful, inventive, and driven.

  Inclusive Recruitment Process:

We welcome all applicants, irrespective of their experience perfectly fitting the job description, as we value diverse and innovative viewpoints. At our organization, individuals who thrive in a culture of continuous learning and inclusive teamwork excel. We are committed to fostering an inclusive and accessible work environment where everyone feels valued, respected, and supported and welcome members of all backgrounds and perspectives to apply. 

Our Commitment:

World Education Services is committed to fostering an inclusive workplace that reflects the rich tapestry of our communities, both in the US and Canada. This commitment is underscored by our unwavering dedication to providing equal opportunities to all qualified individuals, regardless of race, color, religion, sex, national origin, age, disability, sexual orientation, gender identity or expression, veteran status, or genetics. This commitment extends to every aspect of employment, from recruitment and hiring to promotions, training, and benefits. We comply with all applicable federal, state, and local anti-discrimination laws. For us, diversity goes beyond compliance – it's about embracing unique perspectives and cultivating an environment where everyone feels va...