Head of People

Jagger; Toronto; Remote; CAD 180,000 - 250,000; Full time

Job summary

Confidential is seeking an experienced Head of People to own the function as the company scales across Canada and the United States. You will lead recruiting, people operations, compensation, and employee experience in a hands-on, operational role.

Join a fast-growing AI startup at Series B, working with leadership to implement scalable, AI-enabled HR processes that support rapid growth and high performance.

Qualifications

• Significant experience leading People Operations in a high-growth tech company.
• Proven track record building scalable recruiting, onboarding and HR processes.
• Comfort with AI-enabled HR tools and automation to improve efficiency.
• Experience supporting Canada and the United States across employment practices.

Responsibilities

• Own recruiting strategy and execution for technical, commercial, and leadership roles.
• Oversee onboarding, benefits, leaves, employee relations, and offboarding.
• Develop competitive compensation frameworks and performance management discipline.
• Build an AI-first, scalable People function with automated processes.

Skills

People leadership

Talent acquisition

HR strategy

AI in HR

Recruiting strategy

Tools

HRIS / HR tech

Job description

Company: Confidential | Series B AI Startup

Jagger Search has partnered with a rapidly growing, Series B AI startup to recruit their first Head of People. With approximately 120 employees across North America, our client is entering an exciting stage of growth and looking for an experienced People leader to build and own the function as the business scales.

This is a unique opportunity to join the leadership team and take full ownership of talent acquisition, people operations, compensation, and employee experience.

We're looking for a hands-on, commercially minded operator who thrives in high-growth environments, embraces AI and automation, and knows how to build scalable processes without unnecessary complexity or headcount.

What You'll Own

• Lead the company's recruiting strategy and execution across technical, commercial, and leadership functions.
• Partner directly with executives and hiring managers to develop hiring plans and attract exceptional talent.
• Manage an internal recruiter and external recruiting partners.
• Build scalable hiring, interviewing, and onboarding processes that improve talent quality and efficiency.

People Operations

• Oversee the employee lifecycle, including onboarding, benefits, leaves, employee relations, and offboarding.
• Ensure HR operations and employment practices remain compliant across Canada and the United States.
• Own and optimize HR systems, workflows, and people data.
• Partner with Finance on payroll administration and employee-related financial processes.

Compensation & Performance

• Develop and maintain competitive compensation frameworks, including salary bands, equity, promotions, and incentive structures.
• Advise leadership on performance management, employee relations, and organizational challenges.
• Establish consistent, data-driven approaches to compensation and performance decisions.

Building an AI-First People Function

• Leverage AI and automation to streamline recruiting, onboarding, HR administration, and reporting.
• Build repeatable, scalable processes that support continued growth without requiring a large People team.
• Identify opportunities to improve efficiency, reduce manual work, and enhance the employee experience.

What We're Looking For

• Experience leading People Operations and Talent Acquisition within a high-growth technology or SaaS company, ideally at the 50–300 employee stage.
• A proven track record of building and scaling People processes in an entrepreneurial environment.
• Strong recruiting experience, including senior-level and technical hiring.
• Deep understanding of HR operations, compensation, benefits, performance management, and employment compliance.
• Experience supporting employees across Canada and the United States.
• A demonstrated ability to leverage AI, automation, and modern HR technology to improve operational efficiency.
• A practical, business-oriented approach to People leadership, with the willingness to remain hands-on.
• Strong judgment, executive presence, and the ability to advise senior leadership on complex people decisions.

Why This Opportunity?

• First Head of People: Own the function and shape how the organization scales.
• Executive Exposure: Work directly with the leadership team and influence company-wide decisions.
• High-Growth Environment: Join a well-funded, Series B company at a pivotal stage of its journey.
• AI-First Mindset: Build a modern People function with automation and operational efficiency at its core.
• Remote Flexibility: Work remotely while supporting a distributed North American team.

Interested?

If you're an experienced People leader who enjoys building, operating, and scaling within high-growth technology companies, we'd welcome a conversation.