Chief People Officer

September 26 2022
Categories Generalist, HR, Training, Management, Consulting, Relocation, Global mobility
Toronto, ON
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 the People Operations Team, 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 & recruitment) strategy. This is a senior executive position, reporting directly to our Chief Executive Officer.

Specific responsibilities of the position would include:

    • Ensuring the People Operations team is implementing best-in-class People & Culture programs and initiatives, such as analytics, total rewards, workforce planning, international expansion, leadership and employee development, diversity, equity and inclusion, retention and engagement strategies, and organizational change management. 
    • Playing an active role in the diligence and integration efforts 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, Directors and People Leaders, by providing insightful, innovative, and empathetic problem solving.
    • Developing a scalable People Operations strategy in line with the business mission and vision needs, while honoring our values. 
    • Continuing to build upon a performance-based culture focused on setting measurable objectives, 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 that supports recruitment and retention of talent, and also motivates and drives performance. 
    • Providing coaching, mentorship, and development opportunities to ensure continuous learning, the evolution of the People function, and development of the team’s capabilities. 
    • Managing operating budgets for the department, including employee salaries and benefits and all departmental costs. 
    • Partnering with IT, Finance, and Legal to ensure People policies and practices comply with applicable laws, standards, and best practices globally. 
    • 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, breaking down silos and positively impacting alignment. 
    • All duties and responsibilities will be performed in English. 

Required Experience and Qualifications

    • 10+ years of HR/People Operations or related experience, with at least 5 years in a HR managerial position, one of which must have been in a senior leadership position managing a HR department or function. 
    • A bachelor’s degree in business or HR management, or related field. 
    • At least 5-years of global HR management experience with international expansion through organic and inorganic growth (talent acquisition and mergers & acquisitions). 
    • Experience and success managing HR operations at a global SaaS, technology, or technology-enabled business. 
    • Demonstrated ability to conduct due diligence and integrate new companies internationally via mergers and acquisitions. 
    • Ability to lead the building of sustainable diversity, equity, including, and belonging programs. 
    • High level of business acumen with the ability to build relationships, foster collaboration and influence decision-making across an organization using data and various forms of feedback. 
    • Extensive experience preparing and presenting strategic plans and reporting updates to senior leadership teams, board members, and external partners. 
This position is permanent and full-time and will be based out of our business address located at 351 King Street East, 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 4-days per week.
The salary range for this position would be between CAD$200,000 and CAD$280,000, depending on experience level. You will be eligible to receive a discretionary annual bonus, equity in the company, as well as standard company benefits including medical, vision, dental, life insurance, disability coverage, company matching retirement savings and employee assistance programs.
Interested candidates, please send your resumes to:
Relocation costs to be covered by the employer.
About Caseware
Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams are continually collaborating, innovating, and building upon our existing suite of products. With a customer-focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like.
With a recent strategic investment from Hg Capital in 2020, CaseWare is now in its next major growth phase as we double down on the people and products that have made CaseWare so successful to date.
One of Caseware's core values is Many Voices, One Team and with that in mind, we're dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at
Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well.
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