Senior Director - People Operations

Senior Director, People Operations

Boldr · Toronto, Canada (Hybrid) · Full-time · Posted 2026-11-02

Workplace: hybrid

Department: People Operations

Description

A LITTLE BIT ABOUT Boldr

• Boldr is the first global B-Corp dedicated to delivering world-class Client experiences while creating
• access to dignified, meaningful work in communities around the world.
• We are a global team, united by our desire to connect diverse people with common values for boldr
• impact.

LET’S START WITH OUR VALUES

• Excellent. Being excellent at what we do sets us apart. It happens when we care about our work and how it lands, set clear standards, and hold each other accountable. We don't stop at meeting the standard; we keep raising the bar.
• Authentic. Real connection happens when we show up as our best, truest selves, help others dothe same, and stand by each other through the harder times.
• Curious. Curiosity keeps us innovative. Better understanding comes from asking helpful questions, seeking to understand before we act, and building on each other's thinking.
• Dynamic. Growth is central to our purpose, and it only happens in dynamic environments where we stay flexible, adaptable and open.
• Empathetic. Great partnerships happen when we take the time to understand the people we work with, our teams, our clients and our communities, for better outcomes for each.

WHAT IS YOUR ROLE

As Senior Director, People Operations, you are the operational and governance backbone of Boldr's People function. You own the systems, rewards, and standards that let a five-country division run with consistency and care.

Three connected disciplines roll up to you across the Philippines, South Africa, Mexico, Canada, and the United States:

• People Operations and Systems: the employee lifecycle, our HRIS (Rippling), people data, service delivery, and self-service.
• Total Rewards: compensation and benefits, Living Wage governance, pay equity, and job banding.
• Business Partnering: ER cases and investigations, multi-country labor law compliance, risk and audit, and the policies and handbooks that keep us fair and consistent.

This is a role for a builder and an operator. The longer-range strategic agenda, organizational design, performance strategy, and strategic business partnering, sits with the VP and grows alongside our People Success team. Your mandate is to make the backbone genuinely excellent: scalable processes that do not rely on heroics, clean and trustworthy data, sound compliance across every jurisdiction, and a team member experience that reflects our values wherever people work.

You report to the VP, People, and you are one of the leaders the rest of the division depends on to keep the engine running as we scale.

WHY DO WE WANT YOU

We are looking for an impact-driven operator who can give a fast-growing, five-country division the backbone it needs to scale without breaking. Someone who builds systems that last, holds a high bar on compliance and fairness, and still keeps the human center in every process they design.

You will protect organizational health, bring calm and consistency to sensitive moments, and make the everyday experience of working at Boldr feel reliable and fair in every country we operate in. We do all of this so our team members can thrive as we grow.

WHAT WILL YOU DO

People Operations and Systems

• Own the employee lifecycle end-to-end: onboarding, changes, and offboarding, delivered consistently across all five countries.
• Lead Rippling as our HRIS and system of record; design and maintain clean workflows, self-service, and service delivery (ticketing and knowledge base).
• Establish data integrity and reporting discipline: headcount, attrition, and the people data leaders rely on to decide well.
• Partner closely with Payroll to protect accuracy and timeliness in every jurisdiction.
• Modernize People infrastructure through automation and sound system design, so support scales without manual workarounds.

Total Rewards

• Own compensation and benefits governance across all geographies, anchored to our Living Wage philosophy as the pay floor.
• Direct compensation cycles with rigor and clarity: timelines, manager enablement, auditability, and clear communication.
• Oversee job banding and pay structures using our market data source (Payfactors), keeping pay equitable and defensible.
• Steward pay equity and transparency norms that build trust while managing risk appropriately.

Employee Relations

• Oversee sensitive ER cases, investigations, grievances, and disciplinary matters through the Business Partnering team, and personally lead the most complex cases, with consistency, fairness, and empathy.
• Build the ER frameworks and manager guidance that keep outcomes fair and well-documented across countries.
• Serve as a trusted, high-integrity escalation point on difficult people matters.

Compliance, Risk, and Governance

• Ensure compliance across all five countries and both operating models: Managed Outsourcing and Global Employment (EoR).
• Own records, audit, and data protection for People data.
• Translate local labor realities into sound, consistent decisions, flag clearly where in-country counsel is needed, and engage and consult with counsel on these matters .
• Build the governance and risk frameworks that let us scale responsibly.

Policy Development and Maintenance

• Own the development, maintenance, and governance of People policies and employee handbooks.
• Keep policy current with changing labor law in each jurisdiction, and consistent with our values and B Corp commitments.
• Make policy clear, accessible, and genuinely useful to managers and team members, not just technically compliant.

Team Leadership and Stakeholder Partnership

• Lead and develop the People Operations, Total Rewards, and Business Partnering teams; set clear goals, coach for growth, and build a culture of service excellence.
• Own the budget for People Operations, Total Rewards, and Business Partnering, including people, systems, and vendor costs, and ensure it meets company requirements.
• Establish clarity on decision rights, service levels, and escalation paths, so it is clear how People decisions get made here.
• Partner with the VP, the Talent Acquisition and People Success pillars, Business Operations, Finance, and client-facing teams to keep the backbone aligned to the business and company strategy .

Requirements

WHAT LIKE ABOUT YOU

YOU ARE…

• A high-integrity operator who brings calm and clarity to sensitive, ambiguous situations.
• A systems thinker with a bias for action: you ship improvements and then sustain them.
• Fair-minded and consistent, with sound judgment on employee relations, risk, and compliance.
• People-first and business-fluent: you can defend operational decisions in plain, practical terms.
• Tech-savvy enough to modernize People through automation and strong system design.

YOU HAVE…

• 10+ years in People or HR, with 8+ years leading multi-function or multi-country teams across People Operations, Total Rewards, ER, or Compliance including leading managers.
• Proven experience building or rebuilding People infrastructure: operating model, shared services, HRIS, comp governance, and compliance frameworks.
• Strong, varied labor and compliance instincts across multiple countries.
• Demonstrated command of HR technology. Our stack includes Rippling (HRIS), Payfactors (compensation data), Workable (ATS), and Juno (LMS/LXP).
• A track record of leading compensation cycles and governance, including benchmarking, job banding, and pay equity.
• Experience handling sensitive ER matters and investigations with fairness and discretion.
• Excellent judgment and communication. You can push back when needed and keep stakeholders aligned.
• Comfortable working remotely across time zones in a fast-growing, globally distributed team.

NICE TO HAVE…

• Experience in a BPO, outsourcing, or multi-entity services business, including Employer of Record or global employment.
• Fluency with Living Wage or pay-equity frameworks.
• Experience or a desire to work in a certified B Corp or purpose-led environment.

• SHRM-SCP, SPHR, or an equivalent credential (helpful, not required).

  Salary range: CAD 142, 677.24- CAD 178, 346.52 Annually

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