Head of Strategy and Operations
$200,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Not accepting applications on crossover.com at this time.

Description

The hiring function is broken. This is widely understood. What's less clear is how to repair it.

This role exists for someone who can.

Although this position resides within People and Talent Operations, it is fundamentally about systems architecture and operational execution, with hiring serving as the focus domain. You do not need to arrive as a hiring subject-matter expert. What you must bring is expertise in building systems that produce measurable outcomes — systems that scale, repeat reliably, and hold up when tested by real conditions.

The challenge is straightforward to articulate but complex to deliver: architect and run a system that reliably brings qualified talent into the organization, on schedule, meeting the quality standard, and placing them in roles where they perform well and remain. This system cannot only handle tidy, well-scoped requests. It must also accommodate unclear, high-stakes, and atypical scenarios. The role demands sustained ownership, sound judgment, and the rigor to resolve problems in ways that reinforce the system instead of layering on unnecessary complication.

Managing stakeholders is essential. You'll engage with senior leaders who carry firm perspectives, conflicting demands, and incomplete information. You won't possess formal authority. Success will come from earning trust, identifying alignment, and making trade-offs visible — upholding standards while ensuring stakeholders feel acknowledged and supported.

This is an AI-forward operating environment. You'll engage with AI tools directly and consistently, leveraging them to draft content, validate concepts, assess results, examine outliers, and detect trends. You won't delegate ideas to engineers and wait for delivery. Instead, you'll prototype, test, document failures, refine outputs, and then collaborate with technical partners when it's time to productionize or scale.

We also believe in transparency, because we respect your time. This role will not suit everyone.

If any of the statements below resonate with you, this is probably not the right match:

  • You prefer problem identification over owning the full solution lifecycle
  • You depend on hierarchy, organizational structure, or designated owners to drive work forward
  • You delegate all technical execution to engineers rather than building prototypes yourself
  • You interpret constructive feedback or challenge as criticism rather than actionable input
  • You optimize isolated components without considering broader system impact
  • You're drawn to the concept of fixing broken systems more than the sustained work required to do so

This is a globally distributed, remote position offering significant autonomy alongside substantial accountability. You are required to maintain availability for a minimum of four hours that overlap with U.S. business hours on weekdays. Beyond that window, you control your own schedule.

One final note, in the interest of candor: our application process demands meaningful effort. Most applicants invest considerable time, which reflects the nature of the role itself.

If this description energized rather than deterred you, we'd welcome your application.

What you will be doing

  • Architecting and refining complete systems that translate vague requirements into consistent, high-caliber results
  • Engaging directly with senior stakeholders to define true constraints, expose trade-offs, and establish shared definitions of success
  • Applying AI tools regularly to draft, validate, evaluate, and iterate on system elements, then layering in human oversight and quality assurance
  • Maintaining full accountability for your work from conception through delivery, measurement, and refinement — without partial handoffs or shared ownership
  • Recognizing trends, diagnosing underlying causes, and enhancing the system using performance data and field feedback

What you will NOT be doing

  • Identifying issues and delegating implementation to others
  • Improving a single system element without accounting for its ripple effects
  • Relying on formal authority, defined structure, or escalation paths to drive outcomes
  • Routing all technical work through specialists rather than engaging directly
  • Steering clear of complex problems, challenging stakeholders, or personal accountability

Key responsibilities

Architect, own, and iteratively enhance the systems that reliably deliver high-quality hires on schedule and position them in roles where they thrive and remain long-term.

Candidate requirements

  • 5+ years in business operations, people or talent operations, program management, or similarly system-intensive disciplines
  • Proven experience hiring for your own team or function, with measurable accountability for outcomes such as time-to-fill, quality, and retention
  • Demonstrated experience designing and deploying operational systems from start to finish, not solely maintaining existing ones
  • Track record creating organizational and operational artifacts including role specifications, org charts, career ladders, RACIs, workflows, or decision frameworks
  • Strong written communicator: has authored SOPs, process documentation, or post-mortem analyses used by teams
  • Solid understanding of U.S. hiring practices and legal requirements, including compliance factors
  • Proven ability to collaborate effectively with senior leaders in the absence of formal authority
  • Regular, hands-on use of AI in daily operational tasks, with careful attention to quality and inherent trade-offs
  • Capacity to maintain at least four hours of availability overlapping U.S. business hours on weekdays

Nice to have

  • Experience evolving a system across multiple cycles informed by performance metrics and retention analysis
  • Knowledge of low-code platforms, workflow automation tools, or agentic systems
  • Experience designing dashboards or data visualizations tailored for executive stakeholders
  • Prior work in high-growth, high-accountability, or private-equity-backed organizations

Meet a successful candidate

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Andrew Poje
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Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

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