Who you are

• People & Culture Leadership – 5+ years of experience in People Ops, HR, or related roles, ideally in a high-growth, early-stage startup (Series A/B ideal) with ownership over key People functions
• HR Strategy & Execution – Strong balance of strategy and execution across People programs
• Compensation & Benefits – Expertise in payroll and benefits administration
• HR Compliance & Policy Management – Deep understanding of employment law and compliance
• Talent Development & Leadership Enablement – Experience supporting and equipping managers in performance, feedback, and leadership development
• Process Optimization & Tech – Proficiency with HR tech, ATS, and payroll systems (e.g., Rippling, Ashby)
• Confidential & High-Stakes HR Matters – Ability to handle sensitive employee issues with discretion
• Fast-Paced Execution & Prioritization – Strong organizational skills to manage multiple priorities
• Communication & Influence – Excellent ability to engage employees at all levels
• Important note: Data shows that men typically apply when meeting 3/10 requirements, while women often wait until it's 10/10. We encourage you to apply if you see a strong (not necessarily perfect) fit

What the job involves

• We’re seeking a Director of People & Culture to join our team. This is a high-ownership, high-impact individual contributor role. As the sole People team member, you will be responsible for the full employee lifecycle—from hiring to offboarding.
• You’ll oversee payroll, benefits, compliance, employee relations, talent acquisition, and culture initiatives while equipping managers to lead effectively, ensuring our People function evolves alongside our company’s growth
• Talent Acquisition & Recruiting (40%)
• Lead and support hiring efforts, including sourcing, interviewing, and offer processes
• Develop best practices and scalable processes to improve hiring efficiency
• Train and support hiring managers in interview techniques, candidate evaluation, and company hiring processes
• Manage ATS systems to ensure a structured and fair hiring process
• People Operations & Compliance (20%)
• Own and manage all HR policies, documentation, and compliance across the U.S. and Canada
• Maintain and update the employee handbook, create company policies, and ensure legal alignment
• Handle employee contracts, visa processes, and confidential HR matters
• Oversee onboarding and offboarding logistics, including account setup and system access
• Employee Experience & Culture (15%)
• Design and execute initiatives that drive engagement, recognition, and team culture
• Plan and execute annual offsites, weekly All Hands, and team events (both in-person and virtual)
• Champion internal communications that reflect company principles
• Leverage data from monthly employee pulse surveys to enhance the workplace experience
• Performance & Leadership Enablement (15%)
• Own quarterly performance management processes, including reviews and feedback loops
• Develop and implement a manager enablement program to equip leaders with the tools and skills to grow and support their teams
• Provide coaching and guidance on employee relations matters
• Utilize data-driven insights to enhance People programs and policies
• Compensation, Benefits & Payroll (10%)
• Manage payroll and benefits strategy across the U.S. and Canada
• Oversee vendor relationships and serve as the primary point of contact for payroll, benefits, and compensation matters
• Ensure competitive and equitable total rewards programs
• Partner with leadership to define and execute our compensation philosophy

The application process

• Online Application
• Interview with Director of People & Culture
• Interview with VP of Strategy & Ops
• Performance Challenge
• Final 1:1 Interviews
• Final Decision

Benefits

• Dual hubs: experience the best of both worlds with our offices in vibrant Toronto and bustling New York
• Founder access: work shoulder-to-shoulder with our visionary founding team to shape the future of AI
• Growth investment: Accelerate your career with our dedicated professional development budget
• Unlimited time off: recharge and explore with our trust-based, limited paid time off policy
• Comprehensive healthcare: rest easy with our robust health coveage, proioritizing your well-being
• Future-proof savings: Build your financial security through our 401k plan
• Tech enablement: Stay cutting-edge with our technology reimbursement program
• Flexible lifestyle: Achieve work-life harmony with our flexible, trust-based scheduling