Careers at McDougall Insurance

Responsibilities:

• To provide service directly to the client, after the sale by the Sales Executive
• Where appropriate, procure a sale, normally through upgrading and bundling coverage for personal lines clients.
• Communicate with the client in person, by phone, email, etc. to process additions, deletions or changes to their policy on the appropriate broker management system and to provide professional advice or recommendations regarding their coverage.
• Ensure all transactions and renewals are accounted for and processed accurately and on a timely basis.
• Provide quotations or estimates to clients on premiums, data enter work to create files, update information, confirm data and coverage and to record appropriate changes or adjustments.
• Communicate with insurance company personnel as required.
• As an independent broker working for your client, acts as liaison with the insurer and balances the interests of the client, McDougall Insurance and the insurance company in force.
• Function as part of a team responsible for assisting in the collection of accounts receivable and in any other area as required.

Qualifications:

• Must have exceptional customer service skills.
• Must be willing and eligible to obtain a valid RIBO (Registered Insurance Broker of Ontario) license.
• Must be sales oriented and have a working knowledge of the risk and insurance products involved.
• Act in a professional manner at all times and maintain a position of trust and confidentiality.
• Acts in an open, respectful, honest and helpful manner with all team members, clients and other staff.

Responsibilities:

• Sells general insurance policies to the public by acting as the initial contact with the applicant. This can be either personal or commercial coverage.
• Obtains all necessary information from the potential client as required in order to provide for an accurate quotation for coverage and premiums to cover the risk involved;
• Responsible for placing the risk with an appropriate market, obtaining and assisting in the completion of the proper application for insurance; arranging and collecting the premium as per McDougall’s payment terms and forwarding the application to the insurance company to effect or complete the binding of insurance coverage in a timely manner.
• Ensure an abeyance is in place, followed up within a reasonable time to confirm issuance and receipt of the policy, check for accuracy and send to the client;
• Follow up with the client to ensure complete satisfaction and to finalize the sales process;
• Remain in occasional contact both directly and indirectly with the client via other service team members (CSR) to maintain client’s ongoing satisfaction and to provide further products as required in order to build a long term client base and portfolio;
• Responsible for ensuring the timely collection of accounts receivable and any other areas of concern on the portfolio.

Qualifications:

• A valid RIBO or OTL licence is considered an asset.
• Must have exceptional customer service skills.
• Must be sales oriented and have a very good knowledge of the risk and insurance products involved.
• Must demonstrate excellent interpersonal skills and the ability to deal with clients in stressful and contentious situations (e.g. collections, coverage after an incident, etc.)
• Acts in a professional manner at all times and maintain a position of trust and confidentiality.
• Acts in an open, respectful, honest and helpful manner with all team members, clients and other staff.

Responsibilities: 
• Greeting and assisting walk in clients;
• Directing incoming calls;
• Using the customer database to identify the appropriate next steps to best assist the clients needs;
• Sorting and distributing incoming and outgoing mail;
• Preparing and sending material via courier;
• Receiving payments and applying them to the customer database;
• Responsible for daily office accounting, including daily bank deposits;
• Recording information in the financial reporting system;
• Maintain inventory levels and ordering stationary supplies.
Qualifications:
• Must have exceptional customer service and problem solving skills.
• Must have strong organizational skills and the ability to multitask.
• Act in a professional manner at all times and maintain a position of trust and confidentiality.
• Act in an open, respectful, honest and helpful manner with all team members, clients and other staff.
• Experience with Accounts Receivables, MS Word, MS Office, MS Excel.

Responsibilities:

• To provide service directly to the client, after the sale by the Sales Executive
• Where appropriate, procure a sale, normally through upgrading and bundling coverage for commercial lines clients.
• Communicate with the client in person, by phone, email, etc. to process additions, deletions or changes to their policy on the appropriate broker management system and to provide professional advice or recommendations regarding their coverage.
• Ensure all transactions and renewals are accounted for and processed accurately and on a timely basis.
• Provide quotations or estimates to clients on premiums, data enter work to create files, update information, confirm data and coverage and to record appropriate changes or adjustments.
• Communicate with insurance company personnel as required.
• As an independent broker working for your client, acts as liaison with the insurer and balances the interests of the client, McDougall Insurance and the insurance company in force.
• Function as part of a team responsible for assisting in the collection of accounts receivable and in any other area as required.

Qualifications:

• Must have a valid RIBO license and exceptional customer service skills.
• Must be sales oriented and have a working knowledge of the risk and insurance products involved.
• Act in a professional manner at all times and maintain a position of trust and confidentiality.
• Acts in an open, respectful, honest and helpful manner with all team members, clients and other staff.

The McDougall Insurance Group is one of Canada’s largest insurance brokerages, with more than 1,250 employees across 90 locations in Ontario, Alberta, and Nova Scotia. Our IT professionals are aligned to five divisions McDougall, McFarlan Rowlands, Duliban, Drayden, and MHK which in turn support an ever-growing network of locally recognized names. With over a century of success, we combine deep local relationships with an entrepreneurial mindset, and a clear vision to build a modern, scalable organization.

Looking ahead, our ambition is significant: we plan to more than double in size over the next five years through acquisitions and technology-enabled growth. Our IT leader will play a central role in making that vision a reality.

 The Opportunity

This is a high-impact leadership role-not a traditional IT position. You will play a key role in shaping the future of technology within a growing organization, transforming a group of successful but decentralized IT teams into a unified, enterprise-grade function built for scale.

Bringing both hands-on expertise and leadership credibility, you will lead infrastructure and end-user modernization, enable seamless integration of acquisitions, and establish scalable, consistent standards across a multi-division environment. You’ll initially lead the IT team of the largest division, McDougall Insurance & Financial, while influencing across all five divisions, building alignment, trust, and a shared approach to how technology supports the business.

 Responsibilities:

• Direct, mentor, and empower the IT professionals across divisions, building strong partnerships with divisional leadership while driving enterprise technology priorities and fostering a collaborative culture that balances local responsiveness with organization-wide consistency
• Assess and evolve the IT operating model, establishing clear structures, roles, and accountability while shaping a scalable team and organizational design to support ongoing growth
• Lead the consolidation of multiple Microsoft environments into a unified, cloud-based platform, modernizing identity (Entra), endpoint management (Intune), and security capabilities while ensuring the reliability, availability, and evolution of both cloud and on-premises infrastructure
• Maintain reliable, secure, and highly available branch infrastructure and support while transitioning from legacy remote-desktop models to secure, modern end-user computing
• Build and execute a scalable M&A integration framework, leading tenant migrations, user onboarding, identity integration, and device transitions across acquired businesses
• Assess acquired environments and drive pragmatic integration strategies to accelerate synergies, standardization, and operational efficiency across the organization
• Translate business priorities along with technology risks and technical debt into a pragmatic, actionable technology roadmap to support organizational scale and growth
• Develop and manage the annual IT operating and capital budgets, technology procurement, software licensing, and vendor contracts, ensuring investments align with business priorities and deliver measurable value
• Foster and evolve relationships with MSPs, vendors, and external partners, while partnering with enterprise partners in cybersecurity, data, and application development

Qualifications:

• 15+ years of progressive IT experience, including leadership in infrastructure and operations within complex, multi-site environments
• Proven track record of leading large-scale transformations, including cloud migrations, Microsoft ecosystem modernization (Windows Server, Azure, M365, Active Directory, Entra, Group Policy, Intune, hybrid Exchange environments), and M&A integrations
• Hands-on expertise in modern, cloud-first architectures, with strong knowledge of identity, endpoint management, and cybersecurity fundamentals
• Experience designing and supporting enterprise virtualization, storage, backup, and disaster recovery solutions (e.g., VMware vSphere/ESXi, SAN infrastructure, Veeam Backup & Replication)
• Skilled at leading through influence in decentralized or matrixed organizations, building alignment without formal authority, communicating effectively with executives, and leading organizational change across both technical and non-technical teams
• Experience in high-growth, acquisition-driven organizations, ideally within regulated, distributed industries (e.g., insurance, financial services, healthcare)
• Exposure to enterprise-level capabilities, including cybersecurity governance, enterprise architecture, and data platforms

Position Overview

McDougall Insurance is seeking a highly organized, professional, and proactive Executive Assistant to provide high-level administrative, operational, and project support to the McDougall Insurance leadership team.

This is a highly confidential and trusted role requiring exceptional judgment, communication skills, attention to detail, and the ability to manage competing priorities in a fast-paced environment. The successful candidate will act as a key point of contact for senior leadership and a wide range of internal and external stakeholders.

Key Responsibilities

Executive and Administrative Support

• Provide comprehensive, high-level and highly confidential administrative support to the McDougall Insurance leadership team.
• Manage and coordinate the schedules and calendars of the Leadership Team, proactively identifying scheduling conflicts and working with the Leadership Team and internal/external stakeholders to resolve them.
• Support the planning and execution of leadership meetings, events, presentations, and other corporate activities.
• Coordinate internal and external meetings, including scheduling participants, securing meetings locations or sending virtual meetings links, preparing agendas and materials, and managing follow-up.
• Coordinate travel arrangements for members of the Leadership Team, including flights, ground transportation, accommodations, itineraries, meeting schedules, and related logistics. Travel will occasionally be required.
• Coordinate and assist with hosting clients, business partners, industry representatives, and other guests visiting McDougall Insurance.
• Ensure boardrooms and meeting spaces are professionally prepared ahead of meetings with internal and external stakeholders, including arranging beverages, company gifts, presentation materials, technology, and other required details to create a polished, welcoming experience that reflects our brand.
• Support planning and coordinating executive dinners, lunches, receptions, corporate functions, leadership meetings, and other business events, coordinating catering, meeting rooms, guest accommodations, and other event logistics.
• Coordinate the Leadership Team’s participation in conferences, industry and community events, meetings, and other external arrangements.
• Prepare meeting agendas, briefing materials, presentations, and other documentation as required by the Leadership Team, attending meetings as required to take notes, and coordinate follow-up.
• Prepare correspondence, emails, briefing notes, reports, memos, and other communications on behalf of the Leadership Team.
• Screen, prioritize and appropriately direct incoming requests and communications directed at the Leadership Team from internal and external stakeholders.
• Assist with expense reporting, invoice processing, credit card reconciliation and other administrative financial matters as required.
• Maintain a high level of confidentiality at all times when dealing with sensitive business, financial, strategic, and organizational information.
• Anticipate the needs of the Leadership Team and proactively identify needs and opportunities to improve organization, communication, and efficiency.
• Maintain accurate records, files, reports, and documentation.
• Serve as a trusted resource to the Leadership Team, helping ensure that priorities, commitments, meetings, travel, events and communications are effectively coordinated.
• Provide additional administrative and project support to the leadership team as required.

PowerPoint and Presentation Development

• Create and update professional PowerPoint presentations and/or presentation decks for Leadership Team meetings, company events, conferences, employee communications, individual Executive presentations, corporate events and external presentations, maintaining consistency with McDougall Insurance branding and presentation standards.
• Take information, data, and ideas provided by the Leadership Team and turn them into clear, concise, and visually appealing presentations.
• Research and incorporate relevant information, graphics, charts, and supporting materials.

Corporate Communications and Content

• Assist in developing internal and external communications on behalf of McDougall Insurance and the Leadership Team.
• Research and compile relevant industry news, articles, statistics, announcements, and other information to support company communications.
• Draft and/or coordinate company announcements, leadership communications, updates, newsletters, and other corporate communications.
• Proofread and edit written materials to ensure accuracy, clarity, professionalism and consistency.
• Maintain an organized file of corporate communications, articles, presentations, photographs, and related materials.

Excel, Reporting and Data Management

• Utilize Microsoft Excel to organize, analyze, and present business information.
• Prepare spreadsheets, reports, summaries, tracking documents, and dashboards and required.
• Support the Leadership Team with reporting and analysis by organizing data into useful, digestible formats.
• Generate and maintain tracking tools for projects, initiatives, meetings, action items, and other leadership priorities.
• Assist with the preparation of recurring management and executive reports.
• Ensure spreadsheets, reports, and supporting information are accurate, current, and professionally presented.

Project and Leadership Support

• Monitor deadlines, action items, and deliverables and proactively follow up with appropriate individuals.
• Coordinate information and deliverables between departments and members of the Leadership Team, supporting the monitoring of deadlines and action items, and proactively following up with the appropriate individuals.
• Support the coordination of cross-functional initiatives involving multiple departments or stakeholders.
• Assist with special projects and initiatives as assigned by members of the Leadership Team.
• Conduct research and prepare summaries or briefing materials to support executive decision-making.

Qualifications & Skills

• 3-5+ years of experience in an Executive Assistant, Senior Administrative Assistant, Office Manager, Business Coordinator, or similar role; experience supporting senior leadership or executives is considered an asset.
• Experience in a corporate, professional services, financial services, insurance, or similar business environment in considered an asset.
• Exceptional organizational and time-management skills, with the ability to manage multiple priorities and deadlines simultaneously.
• Advanced proficiency in Microsoft Office, particularly Excel, Outlook, Word, and PowerPoint, with the ability to create polished reports, presentations, spreadsheets, and executive materials.
  • Strong PowerPoint presentation development and formatting skills
  • Strong Excel skills, including the ability to organize, manipulate, summarize, and present data.
• Excellent written and verbal communication skills, with strong attention to grammar, tone, and detail.
• Strong interpersonal skills and the ability to interact confidently with executives, employees, clients, partners, and other stakeholders.
• Demonstrated ability to draft professional correspondence, communications, presentations, and other executive-level materials.
• Exceptional judgment, professionalism, and commitment to maintaining confidentiality.
• Excellent problem-solving skills and the ability to work independently.
• Strong attention to detail and a commitment to producing accurate, high-quality work.
• Experience coordinating complex calendars, meetings, events, and travel arrangements.
• Flexibility to accommodate changing priorities and occasional travel as required.