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VP of People Operations; Remote

Remote / Online - Candidates ideally in
Mississauga, Ontario, Canada
Listing for: Crossover
Full Time, Remote/Work from Home position
Listed on 2026-03-06
Job specializations:
  • HR/Recruitment
    Regulatory Compliance Specialist, HR / Recruitment Consultant
Salary/Wage Range or Industry Benchmark: 200000 CAD Yearly CAD 200000.00 YEAR
Job Description & How to Apply Below
Position: VP of People Operations (Remote) - $200,000/year USD
What You Will Be Doing

Creating role specifications, organizational charts, career ladders, and RACI matrices that convert genuine business requirements into precise hiring objectives

Constructing AI‑powered job advertisements and distribution frameworks that draw in qualified candidates without relying on manual sourcing

Engineering screening and evaluation systems that measure skills, judgment, and transferable experience beyond what resumes reveal

Utilizing working knowledge of U.S. hiring regulations and practices to advise stakeholders and identify compliance risks (e.g., W‑2 vs. 1099, EEOC, ADEA concerns)

Recording your reasoning, research, and decisions, then using AI to produce drafts, variations, and scaled analyses

Leveraging post‑hire performance and retention metrics as feedback loops to refine role design, assessments, and talent pipelines

What You Won’t Be Doing

Conducting candidate sourcing, resume reviews, or initial screening interviews

Serving as a bottleneck for hiring information or centralizing all communication through yourself

Waiting passively for stakeholders to request updates

Adhering to conventional recruiting frameworks or "industry best practices" without critical evaluation

Permitting non‑compliant or high‑risk hiring requests to proceed without challenge

Operating in a setting with tight supervision or detailed step‑by‑step guidance

VP Of People Operations

Key Responsibilities
Design and maintain an AI‑driven hiring infrastructure that consistently delivers high‑quality hires on schedule and leverages post‑hire performance and retention data to refine hiring signal over time.

Basic Requirements

A minimum of 5 years of experience in recruiting, talent operations, talent enablement, or people operations

Demonstrated experience designing or managing assessment‑driven hiring pipelines

Proven ability to create organizational artifacts such as role specifications, org charts, career ladders, RACIs, or competency frameworks

Working knowledge of U.S. hiring regulations and practices, including compliance requirements

Confidence engaging directly with senior leaders and C‑suite stakeholders

Excellent written and verbal communication skills with a preference for clarity, structure, and actionable outcomes

Capability to work independently in a global, remote setting

Practical experience integrating AI into daily workflows, including awareness of risks, trade‑offs, and quality assurance

Availability for a minimum of four hours overlapping U.S. business hours on weekdays

Nice‑to‑have Requirements

Experience in organizational design, HRBP roles, or workforce planning

Familiarity with low‑code platforms, automation tools, or agentic workflow design

Experience creating dashboards or data visualizations tailored for executive audiences

Background working in high‑growth, high‑accountability, or private‑equity‑backed organizations

About Crossover
Crossover has been a pioneer of the remote work model since our inception in 2014 – helping thousands of people advance their careers. We specialize in full‑time, long‑term remote jobs – not short‑term "gigs" or part‑time freelancing side ventures. Our platform provides businesses with the fairest hiring on earth by basing 90% of the decisions on objective assessments of a candidate's skills and abilities to perform Real Work.

Since we are 100% remote, people can work from anywhere and earn standardized and competitive compensation, regardless of where they choose to live.

Working with Crossover
This is a full‑time (40 hours per week), long‑term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult  for more details on this topic.

Crossover Job Code: LJ‑4435‑CA‑Mississa‑VPof People Oper

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