Head Of Learning Development Jobs in Toronto, ON

Department:

Underwriting

Location:

Toronto, Calgary, Vancouver or Montreal

Reports To:

Head of Field Underwriting & Distribution and General Manager, North American Construction

Company Overview:

Liberty Mutual Canada is the Canadian operation of Liberty Mutual Insurance Company. We offer a broad suite of commercial insurance products and solutions to mid-size and large Canadian companies with Canadian, North American and/or multinational risks. Liberty Mutual Canada has over 300 employees and services its clients coast-to-coast from our regional offices in Vancouver, Calgary, Toronto, Montreal and Halifax.

At Liberty Mutual Canada, diversity is about all of us. Our promise to you is a culture that is collaborative, rewarding and empowering. We are committed to attracting and retaining employees across all dimensions of diversity and believe that recognizing, appreciating, and applying the unique insights, perspectives and backgrounds of each person cultivates an atmosphere of trust and respect. At Liberty Mutual Canada, our values are to foster a high-performing, equitable and inclusive culture where the best talent of all backgrounds can bring their whole selves to work and succeed.

If you are unsure whether or not your experience matches every requirement below, we encourage you to apply anyway. We are looking for varied and diverse perspectives and experiences that we can add to our team!

Our core values guide all of our decision-making and come to life through our benefits and employee programs. We offer:

· A premier flexible work environment (a combination of on-site & remote work) supporting our employees in their pursuit of a healthy work-life balance

· Competitive health & dental benefits plan

· Market-leading pension plan

· Competitive time off policy

· External education & tuition reimbursement programs

· Employee & Family Assistance Programs

· An opportunity to get involved and become a member of one of our national employee committees – social responsibility, employee engagement, diversity, equity & inclusion

The Opportunity:

The Head of Construction will build and lead a national, multi-line Construction industry vertical with a region-first go-to-market operating model. This role carries national profit and loss accountability across a Construction portfolio spanning property and casualty lines on an annual and project basis — including property, GL, automobile, contractors equipment/inland marine, builders risk, wrap-up and US workers compensation. The Head of Construction will work closely with Surety and Specialty leaders to maximize cross-line success across surety, professional liability, contractors pollution liability, management liability, cyber, and marine, and will partner with aligned functional leads across risk control/engineering, operations, claims, and technology.

At the core of this role is field underwriting execution — translating the underwriting strategy developed in partnership with the Office of Underwriting into disciplined, consistent risk selection and portfolio outcomes across Canada. The Head of Construction will own the go-to-market and distribution strategy, manage strategic broker partnerships at a national level, and embed regional underwriting pods that bring the vertical to life in market. This leader is accountable for driving profitable growth, maintaining portfolio quality, and ensuring the field operates with the risk selection discipline and appetite alignment required to build a top-quartile Construction book.

This leader will also serve as Liberty Mutual Canada's (LMC) primary connection into the North American Construction vertical — contributing Canadian market insights and portfolio performance strategies into North American strategy discussions, activating cross-border capabilities within the Canadian market, and ensuring LMC's Construction go-to-market approach is informed by and aligned with the broader NA Construction strategy where relevant.

Duties & Responsibilities:

• Champion and model our Liberty Values and Guidelines for Inclusion to drive market leading culture and ensure positive employee engagement.
• Own national profit and loss accountability for the multi-line Construction vertical; set portfolio objectives, monitor execution against plan, and ensure performance visibility in collaboration with the Office of Underwriting (OOU).
• Develop and execute a region-first go-to-market strategy – deploying regionally-embedded underwriting pods to win mid-to-large annual contractor and project business, supported by centralized centres of excellence where efficiency and consistency demand it.
• Execute the underwriting strategy developed in partnership with the OOU — translating appetite, risk selection criteria, portfolio limits, and aggregation controls into consistent field-level decisions; partner with OOU on governance, wordings, tools, and referral frameworks.
• Lead, recruit, develop and retain a national Construction team including national resources and oversight of regionally-embedded underwriters in Western Canada, Ontario, Quebec and Atlantic Canada.
• Drive bilingual capabilities and regional responsiveness in Quebec and other provinces as required.
• Own the national broker strategy for Construction — building and managing strategic broker partnerships that improve hit rates, retention, and multi-line share of wallet; serve as primary liaison with Surety leadership to amplify contractor insights and maximize bid success.
• Partner with Specialty leaders (Environmental, Cyber, Financial Lines, Marine) to identify and capture multi-line opportunities; ensure the team is actively pursuing and tracking cross-line wins within the vertical.
• Coordinate with Regional Leaders to ensure Construction underwriters are integrated into regional servicing models and aligned with broader P&C activity across industry segments.
• Engage actively with the North American Construction vertical — contributing Canadian go-to-market insights, broker dynamics, and portfolio performance into NA strategy and planning discussions; leverage NA capabilities, cross-border products, and distribution resources to accelerate profitable growth within the Canadian vertical.
• Collaborate with Risk Control/Engineering to shape pre-bind surveys, post-bind service plans and hiring and prioritization of national risk control/engineering resources in support of the vertical’s risk selection and loss mitigation objectives.
• Work with Claims leadership to appoint Construction claims liaisons, ensure effective large loss reviews, subrogation approaches and claim trend monitoring that inform underwriting action.
• Support program development (e.g., Master Builders Risk) and operational readiness (Account Analysts, Underwriting tools etc.).
• Provide input into financial planning and monthly reporting for Construction results and support the development of five-year growth plans to achieve 2030 portfolio ambitions.
• Represent Liberty Mutual Canada in market forums and act as a senior ambassador for the Construction vertical with brokers, clients, and industry stakeholders.

Skills & Qualifications:

• 15+ years of commercial underwriting experience with meaningful exposure to Construction lines of business. Significant prior leadership and people management experience required.
• Proven track record of building, scaling and managing profitable multi-line portfolios – with demonstrated ability to execute against an underwriting strategy and contribute meaningfully to its development.
• Strong people leadership capability – demonstrated success recruiting, developing, and retaining high-performing underwriting teams across geographies; ability to set direction, hold teams accountable, and build a culture of disciplined risk selection and portfolio ownership.
• Experience operating within a North American or multi-jurisdictional insurance platform — ability to navigate a matrixed organization, contribute to broader North American strategy discussions, and activate enterprise-level capabilities locally while preserving Canadian market nuance.
• Established track record managing strategic broker relationships at a national level — ability to develop and execute a broker strategy that drives hit rates, retention, multi-line penetration, and preferential submission flow.
• Experience leading regionalized operating models, balancing locally embedded underwriting teams with centralized technical resources and governance.
• Strong commercial acumen with P&L responsibility experience; ability to translate portfolio analytics into actionable field-level decisions and go-to-market adjustments.
• Sound working knowledge of Construction lines including surety interplay, contractor finance/WIP, JVs, and PPP exposures — sufficient to lead credibly in market and provide strategic direction to the team.
• Excellent cross-functional collaboration skills – proven relationship-building skills with brokers, clients and internal partners; proven ability to partner across Specialty lines, Claims, Risk Control/Engineering, Operations, and Surety to deliver integrated client and portfolio outcomes.
• Strong communicator, active listener and critical thinker – with the commercial negotiation skills to win in a competitive market.
• Appetite for data-driven decision making; familiarity with portfolio tracking, data coding, and using analytics to steer execution.

This posting is for an active, current vacancy. We do not use AI‑based screening tools in our hiring process. Candidates who complete an interview and remain under consideration may request, and will receive, feedback within 45 days.

Liberty Mutual Canada is committed to fostering an inclusive, accessible environment where all employees feel valued and supported. We are committed to building a workforce that is representative of the communities we operate in and serve. If you require an accommodation for the recruitment/interview process due to a disability (which may be invisible or visible, temporary or permanent), please let us know and we will work with you to meet your needs.