People Services

Summary

Join Fortitude Re as AVP, People Services, and lead the transformation of People operations into a digital, efficient, and employee-centric experience. You will architect scalable service delivery models, automate routine processes, and design systems that empower direct access. This role requires a strong understanding of U.S. and Bermuda payroll operations, compliance with labor laws, and experience with HR ticketing platforms. You will also be responsible for managing Workday administrative tasks, process documentation, and system enhancements. The ideal candidate will possess a creative and innovative mindset, strong communication skills, and a collaborative team-player attitude. This position offers a competitive salary and a generous benefits package.

Requirements

• 6–8 years of experience in People Operations, or HR Services, including hands-on U.S. payroll execution
• WorkDay HCM proficiency required
• Advanced proficiency in SharePoint design and content management
• Experience implementing and managing JIRA, Wrike, Zendesk, or other HR ticketing platforms
• Strong verbal and written communication skills with the ability to clearly articulate complex processes and drive adoption
• Demonstrated success in process improvement, system automation, and stakeholder collaboration
• Proficient in Microsoft Products
• Ability to thrive under pressure

Responsibilities

• Lead the execution of U.S. and Bermuda payroll operations, including tax filings, audits, operational calendars, and payroll vendor oversight
• Serve as the subject matter expert and escalation point for payroll, process execution, and operational inquiries
• Maintain compliance with relevant labor laws and regulatory requirements; prepare and validate reporting such as 401(k), EEO-1, and OSHA
• Set up and manage a ticketing system (e.g., JIRA, Wrike, or equivalent) to streamline intake, triage, resolution, and reporting of People & Culture support requests
• Champion automation of service delivery tools (e.g., ticketing, chatbots/agents, direct access resources)
• Own day-to-day Workday administrative tasks and partner with the Agile team for escalations or feature configurations
• Support colleagues with Workday transactions
• Own the ongoing execution and maintenance of People processes, documentation, and systems enhancements delivered by Agile initiatives
• Own and standardize documentation across employee files, processes, templates, and communications to support compliance, access, and automation
• Analyze surveys and operational metrics, delivering actionable insights that influence workforce strategy and service improvement
• Own and maintain the People & Culture SharePoint hub, centralizing access to SOPs, resources, and policies
• Partner with People Technology to ensure end-to-end delivery aligns with system capabilities and controls
• Collaborates with Agile team members as a process SME, ensuring that solutions align with day-to-day execution and compliance standards
• Continuously reimagine and optimize people processes to improve both efficiency and experience

Preferred Qualifications

• Experience in multi-jurisdiction environments, particularly Bermuda, is a strong plus
• Creative and innovative mindset with great attention to detail
• Collaborative team-player who can work well with various stakeholders

Benefits

• Base Salary Range: $130,000 — $155,000 USD
• Annual bonus based on company and individual performance
• Generous benefits package