Who You Are

You are a seasoned People Operations leader who builds systems that scale, not just processes that survive. You bring deep expertise across People Operations and HR operations, and you know how to translate people data into decisions that matter at the executive level. You excel in environments where there is real work to be done and where your precision and judgment make a meaningful difference. You do not wait for problems to surface; you architect the infrastructure that prevents them.

What You Will Do

Reporting to the VP, People, you will lead the operational backbone of the People function with the autonomy and scope to build something lasting.

• Own the full operational engine of the People function, including HR operations, employee lifecycle, compliance, HR systems, facilities, and workplace experience, so that every employee, from their first day to their last, has a consistent and well-supported experience.
• Design and maintain scalable, compliant HR practices across Canada, the United States, and Colombia, proactively identifying and resolving compliance risk before it surfaces, so that DealMaker can operate confidently across all three jurisdictions without friction or exposure.
• Lead the HiBob strategy from implementation through optimization, ensuring data integrity and reporting that drives executive-level decisions, so that leadership always has the people insights they need to make informed, confident choices.
• Set the standard for People Operations excellence and hold the team accountable for delivering consistent, high-quality outcomes across all programs, so that the People function earns trust as a reliable partner across the business.
• Drive the People function's AI and automation strategy, establishing how the team leverages technology to reduce administrative burden as the company scales, so that your team spends less time on manual work and more time on what matters.
• Partner cross-functionally with leaders and employees to deliver operational HR support that is responsive, accurate, and aligned with business needs, so that every team feels supported and no question goes unanswered for long.
• Transform People data into actionable business intelligence through dashboards and metrics that inform strategy, not just track activity, so that the executive team has a clear and honest view of the health of the organization.
• Oversee facilities and workplace experience, ensuring the physical environment supports a high-performing, engaged workforce, so that the people who come into the office feel that their space reflects how much we value them.

What Skills You Need

You bring a track record of building HR operations that scale with intention. The strongest candidates combine deep functional expertise with a clear view of how technology and data can make the People function smarter and more human at the same time.

• HR Operations & Compliance (8+ years)
• HiBob or comparable HRIS strategy and administration (5+ years)
• People Analytics & Reporting (4+ years)
• Multi-Jurisdiction Employment Law, with direct experience across Canada, the United States, and Colombia or comparable Latin American jurisdictions (5+ years)
• Process Design & Workflow Automation (4+ years)
• Familiarity with employment standards across provincial Canadian jurisdictions, US state-level compliance, and Colombian labor law, including nuances around termination, leave, and benefits obligations in each
• You evaluate and deploy AI tools (Gemini, Claude) with intention, selecting technology based on fit and measurable impact rather than novelty

Bonus points if you have:

• Facilities & Workplace Management
• AI Tooling & HR Tech Evaluation
• Organizational Design & Change Management

This is a hybrid, Toronto based role (4 days in-office in Downtown Toronto).

Founded in 2018 by leading capital markets lawyers, DealMaker has blazed its own trail as the leading online capital-raising platform.As a tech startup, we are well-capitalized, firmly established in our market, and ready to scale. Here's why you should want to join us:

• Competitive compensation with the opportunity to earn equity-get into a growth company on the ground floor
• A diverse & distributed team of doers, innovators, and experts
• Shared employee benefit plan (medical, vision, & dental)
• We love AI and have tools to support you build innovative solutions
• Annual learning support And more!

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