Regan Brennan

Executive Assistant with 10+ years of experience supporting executives, leadership teams, and fast-paced organizations. Skilled in executive calendar management, travel coordination, executive communications, meeting coordination, confidential information management, project support, and workflow improvement. Trusted partner known for anticipating needs, managing competing priorities, and improving operational efficiency through technology and AI tools.

EXECUTIVE OPERATIONS MANAGER / SENIOR EXECUTIVE ASSISTANT at BLKBIRD Media (2020-01 – Present)

Provide executive and operational support to company leadership within a technology-focused organization, managing priorities, communications, scheduling, projects, and business operations.

• Manage executive calendars, meetings, priorities, and daily workflows while proactively resolving conflicts and scheduling challenges.
• Coordinate domestic and international travel, including flights, accommodations, transportation, and changing itineraries.
• Manage executive communications, inbox priorities, and follow-up on critical action items.
• Prepare presentations, reports, proposals, meeting agendas, and executive correspondence.
• Coordinate leadership meetings, internal communications, and cross-functional initiatives.
• Support projects involving technology, operations, vendors, compliance, and business development.
• Manage confidential financial, legal, and operational information with discretion.
• Implement AI tools including ChatGPT to streamline workflows, improve documentation, and increase productivity.
• Build systems and processes that improve organization, communication, and executive efficiency.

LEGAL ASSISTANT at The Law Office (2016-01 – 2020-12)

Provided high-level administrative support to a lawyer while managing confidential legal matters, client communications, and office operations.

• Managed calendar, appointments, deadlines, meetings, and daily priorities.
• Prepared legal documents, correspondence, contracts, and case materials.
• Maintained confidential client files and document management systems.
• Coordinated client communication and professional correspondence.
• Supported legal research, documentation, and administrative processes.
• Managed multiple priorities while ensuring accuracy and meeting deadlines.

ADMINISTRATIVE COORDINATOR at Toronto District School Board (2014-01 – 2017-12)

• Coordinated schedules, meetings, communications, and administrative priorities.
• Prepared reports, presentations, and professional correspondence.
• Maintained confidential records and documentation.
• Supported leadership with organization, planning, and operational coordination.

Master of Education in Education – Medaille University

Bachelor of Design in Design – Ontario College of Art & Design University