Caseware2mo ago

Chief People Officer

Toronto · TorontoFull Time - Permanentexecutive

OtherHr ManagerPeople

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Overview

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,

Technical Tools

OtherHr ManagerPeople

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

We require an experienced, dynamic, and strategic, Chief People Officer to lead People & Culture for a globally distributed workforce across 17 countries, expanding and improving how we support our employees as the company grows, and to define, direct, and own the end-to-end People operations (HR, Payroll & Recruitment) strategy. This is a senior executive position, reporting directly to our Chief Executive Officer as a key leader on the Executive Leadership Team.

This position is permanent and full-time (40-hours per week) and will be based out of our business address located at 351 King Street East, Suite 1100, Toronto, ON. M5A 2W4. While work-from-home will be permitted from time-to-time, the Chief People Officer will be expected to be physically present at our office location up to 3-5-days per week.

Ensuring the People Operations team is implementing best-in-class People & Culture programs and initiatives, such as analytics, total rewards, workforce planning, global workforce planning and multi-jurisdictional employment frameworks, international expansion, leadership and employee development, diversity, equity and inclusion, retention and engagement strategies, and organizational change management.

Playing an active leadership role in the diligence and integration efforts, including people, culture, systems and organizational design, as Caseware continues to grow its global footprint through an M&A strategy.

Acting as a strategic partner to all members of the Executive Leadership Team, Board of Directors and People Leaders, by providing insightful, innovative, and empathetic problem solving on workforce strategy, leadership effectiveness, an organizational performance.

Developing a scalable People Operations strategy in line with the business mission and vision needs, supporting sustained global growth and operational scale, while honoring our company values.

Continuing to build upon a performance-based culture focused on setting measurable objectives, enterprise-wide performance frameworks, developing employee engagement programs, promoting accountability, and encouraging regular feedback.

Developing an employee and candidate value proposition through compensations/rewards, benefits, recognition, learning and development, including global compensation and benefits frameworks, that supports recruitment and retention of talent, and also motivates and drives performance.

Providing coaching, mentorship, and development opportunities to senior people leaders and teams to ensure continuous learning, the evolution of the People function, and development of the team’s capabilities.

Managing operating budgets for the People Operations and Facilities division, including employee salaries and benefits and all departmental costs, across multiple regions and jurisdictions.

Partnering with IT, Finance, and Legal to ensure People policies and practices comply with applicable laws, standards, and best practices globally, including employment, data privacy and regulatory requirements.

Facilitating coordination and management of our workspaces and facilities operations, including vendor relationships, building maintenance, and ongoing office space needs.

Delivering timely and informative internal communications to employees across a globally distributed workforce, breaking down silos and positively impacting alignment, through scalable communication channels, leadership messages, and structured change communications supporting organizational transformation and growth.

All duties and responsibilities will be performed in English.

10+ years of HR/People Operations or related experience, with at least 8 years leading global HR functions, including senior executive leadership of a People department or function.

A bachelor’s degree in business or HR management, or related field; MBA or Master’s degree; or advanced professional HR certifications or executive development is considered an asset.

At least 8-years of global HR leadership experience with international expansion across multiple regions, including both organic and mergers & acquisitions.

Experience and success leading HR operations within a global SaaS, technology, or technology-enabled organization operating at scale.

Demonstrated ability to lead people-related due diligence and post-acquisition integrations activities international, including organizational design, leadership alignment and people systems integration.

Ability to lead the development and execution of sustainable diversity, equity, inclusion and belonging programs across a global workforce.

High level of business acumen with the ability to build relationships, foster collaboration and influence executive-level decision-making across a organization using data, analytics, and various forms of feedback.

Extensive experience preparing and presenting people and workforce strategies, metrics and reporting updates to senior leadership teams, board members and external stakeholders.

Listing Details

Posted: January 29, 2026
First seen: March 26, 2026
Last seen: April 24, 2026

Posting Health

Days active: 29
Repost count: 0
Trust Level: 31%
Scored at: April 24, 2026

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Caseware

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Caseware International Inc. is a global leader in developing audit, assurance, financial reporting, and data analytics software for accounting firms, corporations, and governments. Founded in 1988, the Toronto-based company provides cloud-enabled solutions to over 500,000 users in 130 countries.

Employees

750

Founded

1988

Domain

Jobs

External application · ~5 min on Caseware's site

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