Senior Learning and Development Specialist

Founded in 1966, Masters Insurance has grown into one of Ontario’s largest and most trusted independent brokerages. We specialize in tailored insurance and surety solutions for the construction industry, built on a foundation of strong client advocacy and longstanding industry partnerships.
Driven by our core values of integrity, care, innovation, and exceptional service, we are dedicated to safeguarding our clients' interests and ensuring their peace of mind.
Our extensive services cover personal and commercial insurance, group benefits, as well as life, estate, and investment solutions. With offices in Toronto, Hamilton, Ottawa, Windsor, New York, and Florida, our skilled team partners with top insurers to provide tailored coverage options and prompt, reliable claims support.
Position Summary
The Senior Learning and Development Specialist develops, delivers, coordinates, and improves practical learning across Masters Insurance. Working with the managers responsible for training, department leaders, and subject-matter experts, you will be responsible for translating insurance knowledge, brokerage procedures, and technology workflows into clear, accurate, engaging, and easy-to-use training. This position supports structured onboarding and ongoing development, maintains learning and procedure resources, coordinates training activities, and gathers evidence of learning outcomes.
Key Accountabilities
Work with the managers responsible for training, department leaders, and subject-matter experts to identify learning needs and translate them into clear objectives.
Design, develop, and deliver in-person, virtual, self-paced, and on-the-job training suited to the audience and learning objective.
Build practical, role-based learning for new-hire onboarding and ongoing development, including Account Associate and Account Executive workflows.
Create and maintain visually polished training slides, facilitator notes, exercises, job aids, reference guides, and other engaging learning resources.
Support training on insurance fundamentals, brokerage workflows, client service, Applied Epic and related technology, and compliance or continuing education topics.
Work with subject-matter experts to verify technical accuracy, test process instructions, and obtain content-owner review before publication.
Document and update standard operating procedures and workflow guidance using company standards, including review dates and version control.
Coordinate training calendars, invitations, materials, attendance, follow-up activities, and delivery logistics across offices and teams.
Maintain accessible, organized learning resources and accurate records of training participation, completion, and continuing education as required.
Develop knowledge checks, practice exercises, learner feedback surveys, and other practical measures of whether training objectives were achieved.
Compile participation, assessment results, feedback, and learning gaps; share findings and improvement recommendations with the managers responsible for training.
Support knowledge-sharing and train-the-trainer activities by helping managers and subject-matter experts prepare and deliver training.
Help promote learning opportunities and new or updated training resources; support system changes, process improvements, and related projects.
Candidate Qualifications
Experience in commercial insurance, training and development, learning coordination, or a related role. Brokerage or insurer experience is strongly preferred.
Working knowledge of Commercial Lines insurance products and brokerage workflows.
RIBO licence is preferred; CIP and/or CAIB designation is an asset.
Experience creating and maintaining training content, job aids, process instructions, or standard operating procedures is an asset.
Proficiency with Microsoft 365 applications, including Outlook, Word, Excel, PowerPoint, and Teams.
Experience with Applied Epic is an asset.
Skills & Competencies
Clear written and verbal communication; able to explain insurance, process, and technology concepts in practical terms.
Comfortable facilitating learning for individuals and groups, in person and virtually, and tailoring delivery to different experience levels.
Strong eye for instructional clarity, document consistency, presentation design, and the learner experience.
Excellent organization, attention to detail, and follow-through on training schedules, records, and documentation.
Ability to manage multiple deliverables, work independently, and seek timely input or approval from content owners.
Collaborative approach to working with employees, managers, and subject-matter experts across the organization.
Curiosity, practical problem-solving skills, and a commitment to using feedback and evidence to improve training.
Masters Insurance Limited is an equal opportunity employer dedicated to fostering an inclusive and accessible workplace. We are committed to accommodating the needs of applicants in compliance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act at every stage of the recruitment and selection process. If you require accommodation, please contact us at cclare @mastersinsurance.com.
Masters Insurance takes a fair and transparent, market-based approach to compensation. We recognize that experience and expertise can vary, and we encourage qualified candidates to apply even if their experience or compensation expectations fall outside the stated range. Final offers are determined based on qualifications, experience, skills, and internal equity to ensure consistency and fairness.