Director of People Operations in Toronto

The Director of People Operations will report to the Vice President of Human Resources of Dorado Software Group and will serve as the operational backbone of the People function. This role is responsible for designing and implementing core HR infrastructure across the portfolio, including compensation banding, systems integration, policy documentation, recruitment processes, and employee lifecycle management across multiple countries. The Director of People Operations will manage a Senior People Operations Analyst and work closely with the VP of HR to ensure the operational foundation of the People function is built to support the portfolio’s growth and M&A activity.

This role is based on the East Coast of North America to provide on-the-ground coverage for North America and South America teams during their business hours, while overlapping with the other regions in the morning. This is an opportunity for an operationally strong HR leader to build the People function from the ground up within a global software portfolio backed by Constellation Software.

Key Responsibilities

• Compensation Banding and Benchmarking
  • Map all roles across the business units to standardized bands and titles, globally, across every entity.
  • Link bands to market benchmarks using compensation data sources.
  • Prepare the data foundation for a multi-year compensation harmonization plan designed by the VP of HR.
  • Conduct ongoing compensation analysis for promotions, market adjustments, new hire offers, and internal equity.
  • Build and maintain compensation data in a clean, auditable format.
• Systems Integration, AI Tools, and Data Management
  • Integrate BambooHR, Pinpoint (ATS), Lattice (performance), and multiple country-specific spreadsheets into a connected, reliable data ecosystem.
  • Eliminate duplicate data entry and manual workarounds by building workflows that ensure one update propagates everywhere.
  • Own BambooHR configuration and data integrity globally.
  • Complete the Pinpoint ATS implementation.
  • Evaluate and deploy AI-powered tools and agents to automate repetitive HR operations.
  • Build and maintain AI-enhanced dashboards and reporting for the VP of HR and portfolio leadership.
  • Ensure all employee data handling complies with applicable privacy legislation across jurisdictions.
• Employee Handbook, Policies and Compliance
  • Draft, publish, and roll out a comprehensive employee handbook covering all entities.
  • Document and standardize HR policies aligned with local practices across various regions.
  • Provide training to managers on policies and ensure compliance through coaching and follow-up.
  • Ensure all HR practices comply with applicable employment law in each jurisdiction.
• Recruitment and Talent Acquisition
  • Build the end-to-end recruitment process from hiring requisition through offer acceptance.
  • Create standardized job description templates and interview frameworks.
  • Get Pinpoint fully operational for job postings, candidate pipeline management, interview scheduling, and offer workflows.
  • Partner with hiring managers and external recruiters to fill critical roles.
  • Develop and strengthen the employer brand and employee value proposition.
  • Introduce AI-assisted screening and candidate assessment tools to improve efficiency.
• Onboarding and Offboarding
  • Finalize and document end-to-end onboarding and offboarding processes for all entities and geographies.
  • Ensure every new hire has a structured, consistent experience regardless of location.
  • Track and maintain onboarding plans with hiring managers.
• HR Operating Calendar & Cyclical Processes
  • Create and maintain a calendar of key recurring HR events across the portfolio.
  • Document and publish how these milestones connect to each other.
  • Define all related procedures, inputs, outputs, and roles and responsibilities for each milestone.
  • Train all stakeholders on their specific contributions to each cycle.
  • Ensure the calendar is realistic, well-communicated, and adhered to.
• Employee Relations
  • Act as the primary HR point of contact for line managers and employees located around the world.
  • Proactively partner with managers to address employee relations issues before they escalate.
  • Coach managers on risk, communications, and difficult conversations.
  • Escalate potential disputes to the VP of HR and coordinate follow-up with relevant stakeholders.
  • Navigate North American employment law with confidence.
• Payroll and Benefits Coordination
  • Design and own the payroll coordination framework across all countries.
  • Serve as the senior point of contact for Finance and third-party payroll providers.
  • Ensure the Senior Analyst has the processes, templates, and guidance needed to execute payroll coordination accurately and on time.
• AI and Process Automation
  • Identify and implement AI-driven automation across core HR processes.
  • Develop and maintain automated workflows that reduce manual effort.
  • Partner with the VP of HR to evaluate emerging AI tools and integrate them into the People technology stack.
• Team Management
  • Manage the Senior People Operations Analyst, setting priorities and reviewing work quality.
  • Establish asynchronous communication norms.
  • Use the daily overlap windows effectively for live syncs and collaboration.
• Travel
  • Travel to other Dorado offices and offsites internationally for team meetups, onboarding support, or portfolio events.

Qualifications for Success

• 7-10 years of progressive HR experience with a significant focus on People Operations.
• Has personally built at least two of the following from scratch: compensation banding frameworks, HRIS integrations, employee handbooks, end-to-end recruitment processes.
• Multi-jurisdiction experience across North America, with exposure to employment practices in additional international jurisdictions.
• Strong HRIS and systems proficiency.
• Advanced Excel skills.
• Experience using or implementing AI tools within HR operations.
• Experience managing at least one direct report.
• Excellent written communication skills.
• Detail-oriented, deadline-driven, and takes personal pride in delivering high-quality work on time.
• Experience in software or technology companies is preferred.
• Experience in a multi-entity, portfolio, or holding company structure is preferred.
• Familiarity with BambooHR, Pinpoint, and Lattice specifically is preferred.
• Experience with EOR providers is preferred.
• Experience supporting M&A integration from an operational perspective is preferred.
• CHRL, SHRM-SCP, SPHR, or equivalent HR qualification is preferred.

About Dorado Software Group: We specialize in delivering innovative solutions and exceptional services to meet the diverse needs of our clients. With a strong commitment to quality and customer satisfaction, we strive to exceed expectations and drive success in every project we undertake.