Leo Bailey

Business leader with 10+ years of experience in risk management, strategic partnerships, community engagement, and DEI across the financial services and community development sectors. Skilled in business development and recognized as a relationship-driven leader with strong analytical and strategic capabilities. Proven ability to foster collaboration and deliver results while navigating complex business and organizational environments.

Recipient of a Community Impact Award (2021) and dedicated mentorship advocate with experience in both one-on-one and group coaching models.

Founder and Consultant - Freshwind Consulting - Toronto, ON

(2024-12)

Founded and lead a boutique consulting firm specializing in strategic advisory, digital transformation, and risk consulting for non-profit organizations, government agencies, and small businesses. Focus on practical solutions that empower operational resilience and sustainable growth.

• Consultant: Project Leader for the TD Propelling Black Entrepreneurship program by the Federation of African Canadian Economics
• Executive in Residence: Leading summer seminars and mentorship for York University students in the YSpace program
• Consultant: Led a digital strategy engagement with The Salvation Army, leveraging Microsoft Co-Pilot to streamline organization wide strategy refresh processes, improve data management, and enhance decision-making frameworks across multiple departments. Developed a reporting process and dashboard utilizing MS 365 Power Tools (Automate, BI, SharePoint)
• Term Employment: Delivered a risk consulting project for Payments Canada, identifying operational risks within emerging payments frameworks (Real Time Rails) and providing strategic recommendations to enhance compliance, governance, and resiliency
• Sustainability Consultant: Conducted research and analysis on sustainability practices within Black-owned businesses across Canada for Carleton University
• Developed reports and presentations supporting knowledge dissemination to policymakers, academics, and entrepreneurs.
• Collaborated with researchers and community leaders to highlight pathways for inclusive economic growth.

Part-Time Instructor - George Brown Polytechnic - Toronto, ON

(2025-01)

Instructor at George Brown College delivering Business Concepts (BUS1038) and Small Business Management (BUS1048) to diverse student cohorts. Known for translating real-world industry experience into engaging, practical learning with consistently strong student feedback.

• Delivered instruction for Business Concepts (BUS1038) and Small Business Management (BUS1048), covering core topics in strategy, operations, and entrepreneurship
• Designed and facilitated applied, real-world learning experiences, guiding students through business plans, market analysis, and go-to-market execution
• Earned consistently strong student reviews for an engaging, practical teaching style that connects theory to industry experience

Small Business Partnerships, Director - Interac - Toronto, ON

(2023-01 - 2024-05)

Owned and drove strategic partnerships and portfolio growth initiatives, delivering small business-focused payment education, optimizing onboarding frameworks, and leveraging market insights to increase debit usage, expand business aggregator relationships, and support the evolving needs of small businesses across Canada.

• Secured $750K+ in partnerships across several national entities, ensuring small business focused payments education is available to communities across Canada
• Grew debit usage by 5%+ within the first year of portfolio management via new learning tools and external campaigns
• Forged 8 strategic partnerships, enhancing business aggregator relationships in the segment
• Rationalized payment terminal partnerships for small business owners, developed best practice framework, clarifying merchant onboarding with a reach of 900k plus small businesses
• Developed market data collection to understand technological and business needs of small business owners across Canada including on site business development in Vancouver, Calgary and Montreal

Diversity & Inclusion Director – Office of the CEO - Interac - Toronto, ON

(2021-04 - 2023-01)

Reported directly to the CEO, leading the development and execution of crisis response strategies to address critical social issues, advancing scalable diversity and inclusion frameworks through partnerships with 20+ national organizations, and implementing a best-in-class mental health education platform to support employee well-being while collaborating with executive leadership and key business partners.

• Managed $500K budget, mitigating 5 key social crises and employee impacts, positively impacting employee well being
• Developed a streamlined, scalable diversity and inclusion framework while building relationships with 20+ national community partners
• Liaised and cross-collaborated with 10+ key business partners and executive leadership on world events negatively impacting employees
• Implemented best in class mental health education web app following best practices for procurement and sourcing
• Developed and executed a crisis response framework that included 5+ critical social issues, briefing the CEO and executive committee

Risk Management, Senior Manager - Interac - Toronto, ON

(2019-08 - 2021-04)

Responsible for the implementation of the company's risk management framework, conducting strategic technology risk assessments for high-impact products, fostering cross-team collaboration, championing risk mitigation through awareness initiatives across business lines, and facilitating risk education discussions with industry-leading platforms, while bridging relationships between risk and product leaders.

• Led strategic technology risk assessments, fostering cross-team collaboration for 5 high impact products
• Championed risk mitigation, raising awareness across business lines
• Facilitated collaborative risk education and awareness discussion with industry leading platforms and products
• Bridged relationships between risk function, product and technical teams while developing an understanding of product suite and ecosystem

Senior Manager, Digital Risk & Governance - RBC - Toronto, ON

(2018-05 - 2019-07)

Led risk assessments for product deployments to ensure regulatory compliance, pioneered the agile risk assessment process during a large digital transformation, and developed strategies to integrate risk management with agile processes, while collaborating cross-functionally on digital identification technology risk assessments and enhancing existing risk and technology frameworks.

• Assessed risk for 10+ product deployments, ensuring regulatory compliance
• Led digital identification technology risk assessments, and cross-functional collaboration
• Pioneered agile risk assessment process during large digital transformation
• Developed process and strategy for servicing agile transformation with existing risk and technology frameworks

IT Engagement Manager - RBC Royal Bank - Toronto, ON

(2015-09 - 2018-05)

Managed risk for strategic outsourced IT initiatives, consulting on projects across Wealth Management, Canadian Banking, and Capital Markets, while strengthening governance and enhancing vendor relationships.

• Managed inherent risk of strategic outsourced IT initiatives while limiting exposure to business units and clients
• Consulted and reduced risk for IT projects in Wealth Management, Canadian Banking and Capital Markets
• Connected key governance partners for outsourced IT initiatives, liaising with various functional and technical teams, enhanced vendor relationships for 8 core suppliers while adhering to enterprise best-practices for risk management
• Strengthened governance practices and working relationships with international business units, including Europe and Caribbean via teamwork/effective communication while reducing inherent risk
• Key contributor in various extracurricular engagements including coordinating Blue Water Day, T&O Career Fair and Supplier Risk & Governance Social Committee strategically executing on fiscal year team building goals
• Presented 2016 RBC Royal Performance convention honour for risk mitigation and collaboration
• Achieved CRISC certification in December 2017

Infrastructure Consulting Analyst - Accenture - Toronto, ON

(2011-05 - 2015-09)

Supported the design and execution of application and infrastructure migrations for various clients, ensuring compliance and system stability across large server environments. Monitored key performance indicators for critical systems, contributing to improved operational efficiency. Assisted in the deployment of technical solutions and worked closely with stakeholders to ensure successful project outcomes. Recognized for exceptional teamwork and collaboration in high-pressure environments.

• Integrated business service management software with vendor database, enhancing data synchronization
• Served as primary contact for multiple application and infrastructure environments, ensuring seamless operations
• Ensured accuracy in migration plans, understanding client architecture, key contacts, and operating needs
• Designed migration strategy for high profile North American divestiture including client facing execution in Connecticut and Georgia
• Led 20+ migrations of high availability environments for a leading financial institution

PhD - Entrepreneurial ecosystem of black Canadians and transforming small business to thriving enterprise - Carleton Sprott School of Business (2029)

MBA - Business - Smith School of Business, Queen's University (2017)

BCom. - Business Technology Management - Toronto Metropolitan University (2011)

Certificate - High Performance Coaching - Queen's University Executive Education (2024)

Certificate - Business of Payments - University of Toronto Rotman School of Business (2023)

Certificate - Mental Health for People Leaders - Queen's University (2021)