About Windmill Microlending

Windmill Microlending enables immigrants and refugees to build careers in Canada while reducing poverty and labour shortages. We do this by offering low-interest loans along with career assessment coaching, financial literacy training, and mentorship for newcomers who lack access to mainstream credit.

Since 2005, Windmill has provided over 10,000 loans and supports to newcomers in the fields of healthcare, IT, financial services, law, engineering, and many others, enabling our clients to triple their incomes. Over the past seven years, Windmill has grown its loan portfolio from $5.5M to $45M, with a plan to grow it to $150M–$200M in the next three years. This growth means Windmill’s leadership team requires a strategic, experienced, and collaborative CIO to build a strong technological foundation for the organization that will allow us to scale efficiently for the benefit of our clients.

Windmill is a registered Canadian charity supported by donations and community bonds from the private sector and grants from the public sector.  

The Role

Reporting to the CEO, the National Director & CIO will be responsible for leading a digital transformation journey that is a major pillar of Windmill’s new strategic plan. This leader will drive the implementation and integration of business intelligence tools to improve efficiency, client service and staff satisfaction, while protecting the organization from technology and cyber risk. Leading by example, they will promote a culture that embraces digital literacy and continuous learning.

This leadership team member will take ownership of Windmill’s portfolio of business tools and technological processes. Their primary focus will be on optimizing digital processes, enhancing internal system connectivity, identifying and onboarding new tools to support organizational needs, and anticipating and defending against cyber threats. Working closely with the other Windmill teams and supporting their needs, National Director & CIO will help improve efficiencies, manage risk, and develop solutions that actively support Windmill’s business growth objectives.

Key Responsibilities

Strategy Planning (15%)

• Work with the CEO, leadership team and Board to understand Windmill’s strengths, weaknesses, opportunities and risks from an IT and data perspective
• Develop, define and maintain a strategic technology roadmap that aligns IT initiatives with the organization’s broader business objectives and long-term goals.
• Prioritize initiatives collaboratively based on Windmill’s business needs and resource availability.

Digital Transformation and Team Leadership (25%)

• Lead the organization's digital transformation, leveraging innovative technologies such as generative IT and AI to enhance efficiency, scalability, and impact.
• Lead, manage and develop a small but growing team of high-performing data and IT professionals.
• In conjunction with the National Director, Operations and CEO, lead the development of a digital mindset throughout the organization.
• Lead the adoption of digital solutions across all teams, aided by your superior listening and communication skills.
• Work creatively to deliver innovative solutions while managing expenses.
• Assess emerging technologies and industry trends, anticipating future technological needs and opportunities for innovation.

Systems Integration and Analytics (20%)

• Define, optimize and secure a reusable integration framework to:

Integrate diverse organizational systems, empowering seamless communication, data exchange and analysis.

Identify areas for process optimization and automation, improving efficiencies and reducing operational costs.

Harness advanced analytics to create actionable insights from data that will inform effective decision making and strategic planning

Cybersecurity & Risk (20%)

• Develop and implement robust cybersecurity measures to protect all data and systems from external threats.
• Stay abreast of emerging cybersecurity trends and maintain compliance with industry standards and regulations.
• Conduct risk assessments to identify potential vulnerabilities and mitigate cybersecurity risks.
• Oversee a regular schedule of penetration testing, staff training and other measures to identify vulnerabilities within Windmill’s systems, infrastructure and processes, taking proactive measures to address security risks and protect sensitive information

Vendor Relations (20%)

• Define metrics and KPIs to enable effective vendor management and accountability.
• Manage relationships with technology vendors, ensuring cost-effective solutions that meet the organization's needs, and monitoring vendor performance, making adjustments when required.
• Negotiate contracts and service agreements to optimize value and performance.

The Opportunity

This role offers the chance to be part of the leadership team of a unique, rapidly growing, charitable “bank” whose mission—to integrate skilled immigrants into the Canadian economy—has never been more urgent. The new position of National Director & CIO was created to help Windmill meet its impressive growth objectives by leveraging technology and reducing risk. Candidates from the private sector have a chance to do challenging work in a fast-paced, professional environment while making a powerful and much-needed contribution to Canada’s social and economic fabric.

Experience

Given Windmill is a charitable institution that provides loans, the National Director & CIO will require an understanding of technology as it relates to financial services organizations and, ideally, to lending.

The ideal candidate has a minimum of 10 years of progressive experience in information technology with at least5 years in a senior leadership role, overseeing technology strategy and implementation within the financial services sector. This experience in a lending environment, and extensive knowledge of industry trends and emerging technologies, enables them to develop and execute strategic technology solutions to meet Windmill’s unique needs and challenges.

Demonstrated success in leading technical teams—including recruiting and retaining top technical talent—and managing complex projects from conception to completion is essential. Also important is a track record driving innovation and implementing cutting-edge technologies to facilitate growth in a fast-paced, dynamic environment.

Strong business acumen is also a requirement, to assure the efficient allocation of resources.

Personal Attributes

The successful candidate will be collaborative, strategic, curious, and humble. They are energetic and empathetic, concerned about the welfare of others, and deeply motivated by Windmill’s mission and values.

Able to work both independently and collaboratively as a team player, the successful candidate will have a high degree of accountability for their team’s deliverables and as a leadership team member for the organization’s best interests. They are curious and innovative, with a natural drive to improve how things are done while respecting the contributions of current staff. Naturally entrepreneurial, they will relish the chance to contribute to an important and growing organization.

Core Competencies

• Bachelor's degree in Computer Science, Information Technology, or a related field.
• Comprehensive expertise in cybersecurity, technical architecture, and vendor management.
• Strong understanding of Generative AI, and other emerging technologies.
• Exceptional strategic planning and problem-solving skills.
• Excellent communication and interpersonal abilities, with a track record of building strong relationships across all levels of an organization.
• Demonstrated ability to drive change and lead teams in a dynamic and fast-paced environment.
• Extensive knowledge of systems integration, business intelligence tools, and digital optimization techniques.
• Strong understanding of risk management principles, with experience in implementing effective risk mitigation strategies and protocols.
• Demonstrated expertise in leading technology initiatives in financial services is highly desirable.
• Strong leadership abilities, with a track record of building and motivating high-performing teams to achieve strategic objectives.
• Excellent project management and change management skills.
• Proficiency in French is an asset

Location

• Ideally the candidate is located in Calgary or Toronto, although those in other parts of the country will be considered.
• Some travel is expected within Canada.

How to Apply

We thank all candidates in advance. We will, however, contact only those selected for an interview. To apply, please submit, in confidence, a resumé along with a cover letter that sets out your interest in the role and highlights your relevant experience. Please include your salary expectations in your cover letter. The preferred method of application is online at searchsmartconnect.com/jobs.

Windmill is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, colour, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

Contact Details

Sandra Paquette | 416 763 0404 | sandra@searchsmart.ca

Vesna Markovic | 647 608 3595 | vesna@searchsmart.ca