Bishop Street Underwriters (BSU), a RedBird Capital Partners portfolio company, is a specialty insurance holding company with a portfolio of underwriting businesses (OpCos) operating across the United States, Canada, and the United Kingdom with approximately 300 employees. The Human Resources function delivers centralized talent, payroll processing, benefits administration, and HR systems — enabling each OpCo to focus on underwriting excellence.

The Global HR Leader at Bishop Street Underwriters will be responsible for building and leading the HR function across BSU (the HoldCo) and all of its Operating Companies (OpCos) in the United States, Canada, and the United Kingdom. Reporting directly to the Chief Administrative Officer, this individual will set global HR strategy, drive talent and organizational development, ensure multi-jurisdictional compliance, and oversee the delivery of HR operations — including payroll and benefits — across a growing, multi-entity group.

The successful candidate will bring deep experience leading HR across multiple countries and multiple business units, ideally within insurance industry or another regulated, multi-entity organization. They will be equally comfortable setting strategy with the CAO and executive leadership and rolling up their sleeves to ensure consistent, high-quality HR delivery to every OpCo.

This role will lead a team of four to six individuals and partners closely with OpCo leadership, BSU Operations/Finance, external benefits brokers, and payroll vendors to deliver a seamless, compliant, and consistent employee experience across the group.

Strategic HR Leadership — BSU & OpCos

• Serve as a trusted advisor to the Chief Administrative Officer and senior leadership on all people-related matters across BSU and its OpCos, including organizational design, workforce planning, and culture.
• Develop and execute a global HR strategy that aligns with BSU's business objectives and supports each OpCo's individual growth plans.
• Partner with HoldCo and OpCo leadership to build scalable HR infrastructure, policies, procedures and governance that flex to each entity while maintaining organization-wide consistency.

Talent Management & Employee Experience

• Lead the design and delivery of talent acquisition, performance management, succession planning, and employee development programs across BSU and all OpCos.
• Champion a consistent, positive employee experience while allowing for appropriate local market and OpCo-level nuance in the US, Canada, and UK.
• Oversee compensation and total rewards strategy across the group, ensuring market competitiveness and internal equity across jurisdictions and entities.
• Drive employee engagement, retention, and culture-building initiatives across a geographically dispersed, multi-entity workforce.

HR Operations, Payroll & Benefits Oversight

• Provide leadership and oversight to the Operations Specialists (Payroll & Benefits), ensuring accurate, timely, and compliant payroll processing and benefits administration for BSU and all OpCos in all three countries.
• Continuously evaluate and improve HR operational processes, systems, and vendor relationships (HRIS, ADP Workforce Now, ADP Celergo, benefits carriers/brokers).
• Oversee onboarding of newly acquired OpCos onto BSU's HR, payroll, and benefits platforms.

Employment Law, Compliance & Risk Management

• Ensure full compliance with employment laws and regulations across US (federal and state), Canadian (federal and provincial), and UK jurisdictions for BSU and every OpCo.
• Maintain up-to-date knowledge of evolving labor law and regulatory requirements in each region, engaging internal legal and compliance team as needed.
• Own employee relations matters, investigations, and dispute resolution, ensuring consistent and legally sound practices across all OpCos and locations.
• Develop and maintain HR policies, employee handbooks, and governance frameworks tailored to each jurisdiction and OpCo while maintaining group-wide consistency where possible.

Team Leadership

• Directly manage and develop a team of 2 HR Business Partners and 2 Operations Specialists (Payroll & Benefits), setting clear goals and fostering professional growth.
• Build a high-performing HR team capable of supporting a multi-country, multi-entity underwriting organization with excellence and consistency.

Qualifications & Experience

Required

• 10+ years of progressive HR leadership experience, including experience operating across multiple countries (US, Canada, and/or UK strongly preferred).
• Prior experience as a senior HR leader (Head of HR, VP/Director of HR, or similar) within insurance industry, financial services, or another regulated, multi-entity industry preferred.
• Demonstrated experience managing payroll and benefits operations across multiple entities, either directly or through oversight of an operations team.
• Experience supporting a holding company / multi-OpCo structure, including onboarding newly acquired businesses onto shared HR, payroll, and benefits platforms.
• Bachelor's degree in Human Resources, Business Administration, or related field required; advanced degree or HR certification (SHRM-SCP or equivalent) preferred.

Preferred

• Working knowledge of ADP Workforce Now and ADP Celergo, or comparable multi-country HRIS/payroll platforms.
• Exposure to the insurance, financial services, or professional services sector.
• Experience with M&A-related HR integration and onboarding of newly acquired entities.
• Working knowledge of employment law across multiple US states including California, Ontario/Quebec Canada, and the United Kingdom.

Core Competencies

Bishop Street Underwriters offers a competitive total rewards package commensurate with jurisdiction, experience, and market benchmarks, including: 

• Competitive base salary and annual performance bonus (jurisdiction-dependent). 

• Comprehensive health, dental, and vision benefits (USA) from day one. 

• Employer-matched retirement savings: 401(k) (USA), Group RRSP (Canada), or workplace pension (UK). 
• Private medical insurance (UK) and provincial health plan coordination (Canada), consistent with local market practice.

Equal Opportunity, Accommodation & Work Authorization

• Bishop Street Underwriters is an equal opportunity employer and does not discriminate on the basis of any protected characteristic under applicable U.S., Canadian, or U.K. law. We are committed to providing reasonable accommodation to applicants and employees with disabilities throughout the recruitment and employment process; candidates who require accommodation should contact [HR contact] to make a request.