Enterprise Application Support Lead

Berkley Canada (a Berkley Company); Toronto; Hybrid; CAD 115,000 - 145,000; Full time

Benefits offered by this job

Comprehensive benefits package

Job summary

Berkley Canada is hiring an Enterprise Application Support Lead to oversee core insurance systems including underwriting, policy administration and claims platforms. You will bridge business stakeholders, system vendors and internal tech teams to ensure operations run smoothly.

We value domain knowledge, vendor management experience and a disciplined approach to releases and testing. Hybrid remote/on-site work is supported with a strong benefits package and opportunities for growth.

Qualifications

• 2+ years’ proven experience with an insurer or MGA.
• 4+ years leading IT systems, including configuration, patch releases and version updates.
• 5+ years collaborating with subject matter experts to define system requirements.
• Experience with third-party vendors and vendor relationship management.
• Strong testing, release management and change control in regulated environments.

Responsibilities

• Develop and maintain understanding of Berkley Canada’s core insurance systems, including features and integrations.
• Engage with underwriting, claims and operations to map business needs to system functionality.
• Work with vendors and implementation partners to interpret requirements and oversee delivery.
• Track defects and oversee vendor resolution, testing and sign-off.
• Plan and oversee version upgrade cycles and determine upgrade adoption.
• Serve as SME for system testing and test planning for new features and fixes.
• Collaborate with Data Engineering to ensure downstream data considerations are addressed.
• Establish standards and best practices for system super users and controls for vendor management.
• Own and maintain key vendor relationships related to core applications.

Skills

Communication skills

Vendor management

IT systems leadership

Cross-functional collaboration

Regulatory compliance

Education

CS/IS/Business Management degree

Tools

Release management tools

Job description

Why Berkley?

Berkley Canada is a boutique Specialty and Accident, Health & Travel Insurer that delivers exceptional expertise and service to our broker partners and insureds. Our mission is to be the best for our employees, customers and shareholders. By being the best, we mean generating better experiences and better outcomes for these three stakeholders. In order to achieve this, our strategy is simple; we find the industry expert in a line of business and empower them to better serve that specific niche. We encourage our team to think outside the box, be innovative and create new opportunities. Join us today!

Company Details

Why Berkley?

Berkley Canada is a boutique Specialty and Accident, Health & Travel Insurer that delivers exceptional expertise and service to our broker partners and insureds. Our mission is to be the best for our employees, customers and shareholders. By being the best, we mean generating better experiences and better outcomes for these three stakeholders. In order to achieve this, our strategy is simple; we find the industry expert in a line of business and empower them to better serve that specific niche. We encourage our team to think outside the box, be innovative and create new opportunities. Join us today!

Responsibilities

This role is open to Manager-level or Director-level depending on candidate’s experience and qualifications

Position Summary:

We are looking for an Enterprise Application Support Lead to oversee the configuration, maintenance and ongoing support of Berkley Canada’s core insurance business systems, including underwriting, policy administration and claims platforms. This role serves as a key bridge between insurance business stakeholders, system vendors, and internal technology teams, ensuring core systems continue to meet operational, data and control requirements. The successful candidate will bring strong commercial insurance domain knowledge, experience working with third‑party system vendors, and a disciplined approach to system support, change and release management.

• Develop and maintain a deep understanding of Berkley Canada’s core insurance systems, including features, configuration, integration points and operational dependencies.
• Engage closely with underwriting, claims and operations stakeholders to understand business needs and map these to system functionality and configuration options.
• Work with system vendors and implementation partners to interpret requirements, develop implementation approaches, oversee delivery and hold vendors accountable for outcomes.
• Track and manage system defects; facilitate prioritization, analysis and development of workarounds; oversee vendor resolution of defects, user acceptance testing and release.
• Plan and oversee version upgrade cycles, staying informed of new system features and functionality and determining when and how upgrades should be adopted.
• Serve as a subject matter expert for system testing, including development of test plans for new features, defect fixes, regression and integration testing; oversee test execution and sign-off.
• Collaborate with the Data Engineering team to ensure changes to core systems appropriately consider downstream data, analytics and reporting requirements.
• Establish and promote frameworks, standards and best practices for system super users who manage business configuration and insurance policy issuance.
• Establish, document and periodically test controls related to third‑party application release management and vendor management.
• Own and maintain key vendor relationships related to core insurance applications.

You will also have the chance to...

• Make a noticeable impact on a small but growing team where the benefits of your contributions will be highly visible to the rest of the organization.
• Draw from resources and expertise available in the wider Berkley Group of companies.
• Enjoy a competitive benefits package including a personal budget for professional development.
• Join a supportive and empowering company culture that recognizes and values the diversity of our people.
• Work flexibly in a hybrid remote/on-site environment.

Qualifications

Characteristics:

• 2+ years’ proven experience working for an insurance company or Managing General Agent.
• Experience working for a commercial property and casualty insurer is strongly preferred.
• 4+ years’ experience in a lead role supporting business IT systems, including management of application configuration, patch releases and version updates.
• 5+ years’ experience collaborating with business subject matter experts and system super users defining requirements for system functionality and IT support processes.
• Experience working with third‑party system vendors, including requirements interpretation, delivery oversight and vendor relationship management.
• Solid understanding of system testing disciplines, release management and change control in a regulated environment.
• Ability to understand and articulate how system changes impact downstream data, reporting and analytics.
• Strong communication skills with the ability to work effectively with both technical and non-technical stakeholders.
• Highly organized, detail-oriented and comfortable operating in a control-conscious environment.
• Collaborative, pragmatic and solution-focused approach.
• Post-secondary educational qualification in computer information systems, computer science or business management preferred but not required with relevant work experience.

Thank you for considering Berkley Canada!

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability or any other legally protected basis, in accordance with applicable law.

Additional Company Details

• Base Salary Range: $115,000 - $145,000
• Eligibility for an annual discretionary bonus
• Comprehensive benefits package, including health and dental coverage, life insurance, STD, LTD, critical illness insurance, EAP, professional development support, vacation, paid time off, and RRSP plan contributions

Our salary ranges are determined by role, level, and location. The range displayed reflects the minimum and typical maximum target for new hire salaries for this position; it does not reflect the maximum salary for the role over time. Within the range, individual pay is determined by job related skills and experience demonstrated during the interview process.

Berkley Canada does not use AI based screening tools in the hiring process and this posting is for an existing vacancy that we are actively hiring to fill.