Remote Head of Recruiting Ops for Elite Exec Searches

Kibbi Technologies Inc.; Toronto; Remote; CAD 248,000 - 290,000; Full time

Job summary

Crossover is hiring a Head of Recruiting Operations for a fully remote, long-term role. You will own and optimize scarce requisitions, align executive stakeholders, and build AI-powered tooling to improve hiring outcomes.

The position requires extensive leadership in recruiting, a track record with executive decisions, and strong documentation. Compensation is US$100 per hour, with weekly payments, and full remote flexibility across regions.

Qualifications

• 8+ years in recruiting, talent acquisition, or executive search, with focus on hard-to-fill or executive-level roles.
• Directly worked with executive decision-makers as the accountable owner and documented disagreements.
• Built or revised hiring assessments using outcome data.
• Daily use of AI tools and ability to name a work product made with them in the last 3 months.
• Produced compensation benchmarking or market-sizing analyses for executives.
• Spotted US hiring compliance risks: pay bands, worker classifications, pay transparency rules.
• Overlapping US business hours by at least 6 hours per weekday.

Responsibilities

• Close the hardest requisitions and scarce talent searches.
• Align executives with conflicting criteria and rebuild trust.
• Fix assessment systems and AI rules that drift.
• Build point solutions with Claude Code, Lovable, and MCPs.
• Provide pipeline diagnoses, compensation benchmarking, and market sizing.
• Handle questions with minimal information and keep commitments until close.

Skills

Executive stakeholder management

Documentation

AI tooling integration

Analytical thinking

Market benchmarking

Project management

Cross-functional collaboration

Tools

Claude Code

Lovable

MCPs (Model Context Protocol servers)

Low-code platforms

Job description

Crossover is hiring a Head of Recruiting Operations for a fully remote, long-term role. You will own and optimize scarce requisitions, align executive stakeholders, and build AI-powered tooling to improve hiring outcomes.

The position requires extensive leadership in recruiting, a track record with executive decisions, and strong documentation. Compensation is US$100 per hour, with weekly payments, and full remote flexibility across regions.