Berkshire jobs in North York, ON

Who We Are:

Berkshire Hathaway Specialty Insurance (BHSI) is a strategic and trusted insurance partner providing a broad range of commercial property, casualty, and specialty insurance solutions to customers and brokers around the world. Part of Berkshire Hathaway’s insurance operations, we combine a top-rated balance sheet, disciplined execution, and a global team known for strong capability and strong character.

We are a values-based organization where respect, integrity, excellence, collaboration, and passion define how we operate. We value diversity of background, experience, and perspective, and we foster an environment where teammates are expected to contribute meaningfully, operate with accountability, and continuously raise the quality of the organization around them.

Learn more about our unique culture and history.

Job Opportunity:

Berkshire Hathaway Specialty Insurance (BHSI) has an exciting opportunity for a Product Owner to join our Toronto-based Enterprise Business Solutions team, with an initial focus on HR technology modernization. This role will play a key part in evaluating and moving from a customized HRMS solution to a commercial cloud-based HCM platform such as Workday.

We are looking for someone with strong HR technology and HCM platform experience. Workday HCM experience is strongly preferred. The successful candidate will partner closely with HR business leaders, Technology, implementation partners, and other stakeholders to turn business needs into clear delivery priorities. This includes requirements, user stories, acceptance criteria, process flows, configuration considerations, and testing plans. Just as important, this person will help the business make practical platform decisions that use standard HCM capabilities and avoid recreating unnecessary custom processes.

This is a hands-on Product Owner role for someone who can connect business processes, platform configuration, testing, data, reporting, integrations, and release readiness while staying focused on practical business outcomes.

While the immediate priority is HR technology, the experience gained in this role may also support broader Enterprise Solutions work over time as business needs evolve.

Duties & Responsibilities:

• Own and manage the product backlog for assigned HR technology initiatives, working with HR and Technology stakeholders to set priorities based on business value, risk, operational impact, and delivery capacity.
• Partner with HR business leaders to understand needs, document current-state and future-state processes, and identify practical opportunities to simplify work while using standard HCM platform capabilities to achieve the desired results.
• Translate business needs into clear user stories, functional requirements, acceptance criteria, process flows, data, reporting, security, integration, configuration, and testing needs.
• Support HCM platform implementation activities by partnering with implementation teams on configuration review, business process validation, reporting, security, integrations, data migration, release readiness, and defect triage.
• Work with implementation partners and internal Technology teams to validate proposed designs, review and align on expected system behavior, confirm solutions meet business requirements, and avoid unnecessary customization.
• Coordinate user acceptance testing, including review and business alignment on the test strategy, test planning, scenario development, stakeholder participation, defect tracking, retesting, and business sign-off.
• Coordinate with technical teams on reporting, integrations, data mapping, data quality, validation, reconciliation, and governance activities to confirm business requirements are understood and met.
• Communicate priorities, decisions, risks, dependencies, status, and open items clearly to HR stakeholders, Technology teams, vendors, and leadership.
• Support release readiness, training coordination, production validation, post-implementation adoption, and ongoing improvement for assigned HR business and technology initiatives.
• Champion agile delivery practices across assigned initiatives, helping business and technology teams refine priorities, manage the backlog, plan releases, and deliver work in practical increments focused on business value.

Qualifications, Skills and Experience:

• 5+ years of experience in HR Technology, HRIS, HCM, HR transformation, business architecture, or related enterprise technology roles.
• Strong HR technology and HR business process knowledge, including employee lifecycle data, compliance considerations, reporting needs, and operational impacts.
• Workday HCM experience is strongly preferred, including exposure to HCM business processes, configuration, reporting, security, integrations, testing, release readiness, or implementation support; experience with SAP SuccessFactors, Oracle HCM, UKG, or another comparable HCM platform will also be considered.
• Ability to translate business needs into clear requirements, user stories, acceptance criteria, workflows, test scenarios, and decision documentation.
• Ability to understand standard HCM platform capabilities and partner with implementation teams to design practical solutions while minimizing unnecessary customization.
• Experience supporting UAT, defect triage, validation, stakeholder sign-off, release readiness, or post-production support.
• Strong analytical and problem-solving skills, with the ability to clarify options, identify root causes, and drive practical resolution.
• Experience working in Agile, Scrum, Kanban, or hybrid delivery environments, including backlog management, user story development, sprint planning, and stakeholder demonstrations.
• Strong communication and stakeholder management skills, with the ability to work effectively with HR, Technology, vendors, implementation partners, global teams, and leadership.
• Independently motivated with a team-oriented mindset and the ability to stay focused on delivery, quality, and business outcomes.

Preferred Qualifications

• Experience participating in an HRMS global implementation, platform selection, upgrade, major enhancement, or transition from a custom-built HRMS to a commercial HCM platform.
• Experience working in insurance, financial services, or another environment with regulatory, privacy, audit, or security requirements.
• Ability to understand how business processes, data entities, reporting, integrations, and system relationships interact across the HR technology landscape; comfortable reviewing data models or ERDs, using SQL and XML to support analysis or validation when needed, identifying data dependencies, defining business data requirements, and collaborating with architects, analysts, integration teams, and developers.

BHSI Offers:

• A competitive package and exciting growth opportunities for career-oriented teammates.
• A dynamic, action oriented, and thoughtful environment centered on always doing the right thing for our customers, teammates, and our other stakeholders.
• A purposely non-bureaucratic organization that embraces simplicity over complexity and emphasizes individual excellence in a team framework.
• Benefits that support your life and well-being, which include:
  • Comprehensive Health, Dental and Vision benefits
  • Disability Insurance (both short-term and long-term)
  • Life Insurance (for you and your family)
  • Accidental Death & Dismemberment Insurance (for you and your family)
  • Flexible Spending Accounts
  • Health Reimbursement Account
  • Employee Assistance Program
  • Retirement Savings 401(k) Plan with Company Match
  • Generous holiday and Paid Time Off
  • Tuition Reimbursement
  • Paid Parental Leave

NOTE: Compensation will be commensurate with experience. This job description is not intended to be all-inclusive. Team Member may perform other related duties as negotiated to meet the ongoing needs of the organization.

BHSI complies with Ontario’s Accessibility for Ontarians with Disabilities Act (AODA) and has a process in place that provides accommodations for job applicants and teammates with disabilities (upon request).

The base salary range for this position in Toronto is CAD $140,000 to $165,000, along with annual bonus eligibility. Total compensation for a candidate is determined by their relevant skills, location, and experience. We value our teammates – both their capabilities and character – as demonstrated by our amazing culture.

We do not employ AI or automated tools to filter, assess, or select candidates

This posting is for an existing vacancy within the organization.

Please send resumes to hr@bhspecialty.com

Visit our website at www.bhspecialty.com