W. R. Berkley CorporationVerified Job Source

Director, Enterprise Application Support

Toronto, ON
Hybrid
Posted Aug 14, 2026
1 position

$115,000–$145,000 / year

Opens an external site

Experience level: Senior · 5+ years
Minimum education: Bachelor’s degree
Apply by: Aug 14, 2027
Posting language: English
Working hours: 40 hours per week

Job summary

The Enterprise Application Support Lead oversees the configuration, maintenance, and support of core insurance business systems while acting as a bridge between business stakeholders and technology teams. They are responsible for managing vendor relationships, facilitating system upgrades, and ensuring operational requirements are met through effective release and change management.

Job details

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 Berkley Canada offers a competitive compensation plan and a robust benefits package for full time, regular employees, including: • 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.

What you’ll do

Requirements

Candidates should have over 5 years of experience in business IT systems support and a strong background in the commercial insurance sector. Proficiency in vendor management, system testing disciplines, and the ability to translate business needs into technical configurations are essential for this role.

Benefits

• Health coverage • Dental coverage • Life insurance • Short-term disability • Long-term disability • Critical illness insurance • Employee assistance program • Professional development support • Vacation • Paid time off • RRSP plan contributions • Annual discretionary bonus