VP of People Operations (Remote) - $200,000/year USD

If you're a recruiting professional who has grown weary of manual sourcing, resume screening, and treating CVs as predictors of performance, this opportunity is designed with you in mind. As part of Crossover's People and Talent Operations team, you will architect the entire hiring experience from start to finish. Your role is not to shepherd candidates through a traditional funnel. Instead, you are here to engineer the infrastructure that draws in the right talent, measures genuine capability, and consistently delivers exceptional hires on schedule — hires who meet rigorous standards and remain with the organization. When results fall short, you will not rationalize the gap. You will rebuild the system. Our approach to hiring diverges sharply from traditional models. We do not rely on manual sourcing, resume-centric screening, or a recruiter-gatekeeper structure. Job postings are strategically crafted to reach and engage the ideal audience, including candidates not actively seeking new roles. Screening frameworks are engineered to measure skills, judgment, applicable knowledge, and actual work output well before any hiring team conducts interviews. We also believe in full transparency: our culture is distinct, and not every candidate will flourish here. This is not a critique — it is a matter of alignment. We are committed to respecting candidates' time, so before you proceed with our application, it is essential to understand what this role is not. If any of the following statements resonate with you, we are likely not the right match:

• You prefer to concentrate on sourcing, resume analysis, or conducting initial screening calls.
• You are hesitant to push back on hiring managers when their requests veer into low-value or non-compliant areas.
• You favor receiving explicit directions rather than determining what systems need to be created.
• You view AI as a tool to approach cautiously rather than something to proactively integrate and design around.
• You depend on meetings for alignment rather than creating dashboards, documentation, and proactive status updates.
• You assume retention challenges are exclusively people-management issues and never warrant upstream investigation.

This is an AI-native environment. AI generates initial drafts, alternative versions, analytical outputs, and preliminary passes as standard practice. Your contribution lies in how you structure prompts, establish quality boundaries, document your reasoning, and fine-tune outputs. You will regularly delegate execution to AI, then concentrate on quality assurance, system oversight, and building agentic frameworks that scale efficiently. The position is fully remote and operates globally. You will enjoy significant autonomy, matched by equally high accountability. You will collaborate directly with senior leadership and C-suite stakeholders across a private-equity-backed portfolio, with an expectation of proactive communication and early identification of risks. You must be available for a minimum of 4 hours overlapping U.S. business hours on weekdays, when most stakeholders are active. Beyond that window, your schedule is predominantly flexible. Finally, in the interest of transparency: our application process is not brief. It demands genuine time and consideration. Most candidates spend 1-3 hours during the process, and this role frequently requires additional investment. This is intentional, designed to ensure a strong mutual fit. If reading this has increased your interest, we would genuinely welcome your application. 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. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! 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 www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-4435-US-Chicago-VPofPeopleOper