Senior Director - People Operations

The Senior Director, People Operations serves as the operational co-pilot to the Chief People Officer (CPO), translating Crunchtime’s executive people strategy into scalable, compliant, and data-driven global operations. This leader oversees the day-to-day engine of the People organization—directing global HR infrastructure, total rewards execution (payroll collaboration with Finance, benefits, and compensation administration), HRIS architecture, data analytics, regulatory compliance, and employee lifecycle mechanics.

Operating across domestic and international teams, the Senior Director manages the operational backbone that supports company-wide scaling, performance management cycles, M&A integrations, and positive employee experiences. This leader will drive policy and operational harmonization across our global offices, including main hubs in the US, UK, Australia, and Mexico.

Core Responsibilities

Strategic Partnership & Operational Execution

• Serve as the CPO’s operational deputy, converting the executive People roadmap, cultural goals, and workforce plans into actionable departmental OKRs, project plans, and scalable service delivery models.
• Manage the People Operations department budget in partnership with the CPO, monitoring expenditures across benefits, HR technology, vendor platforms, swag, and company events.
• Lead, mentor, and scale the People Operations team—establishing operational rhythms, performance metrics, and high standards of service, accuracy, and responsiveness.
• Support organizational scaling and M&A integration activities, leading due diligence review, HRIS/payroll migrations, policy harmonization, and operational workforce assimilation.

Total Rewards Operations, Payroll & Vendor Management

• Oversee the end-to-end operational delivery of payroll, statutory deductions, and global compensation administration in close coordination with Finance.
• Partner with the CPO on compensation structure execution, job leveling, and career matrix operationalization to ensure roles reflect competitive market conditions.
• Direct global benefits administration, annual renewals, leave of absence management, and accommodation programs in collaboration with brokers and regional providers.
• Manage strategic relationships, RFPs, SLAs, and contract terms across all third-party People vendors, including EOR/PEO providers, benefits brokers, and screening partners.

Systems, Architecture & People Analytics Maturity

• Own the enterprise HR tech stack end-to-end (HRIS, onboarding workflows, performance platforms, and data integrations), driving ongoing automation and AI fluency to eliminate manual administrative friction.
• Collaborate closely with Recruitment to ensure a secure, seamless ATS-to-HRIS data pipeline
• Establish robust People data analytics and reporting maturity, building executive dashboards and KPIs to track retention, turnover, engagement trends, and headcount forecasts for CPO and leadership review.
• Implement and enforce data governance, role-based security access, record retention schedules, and audit controls across all workforce platforms.

Global Compliance, Legal Risk & Policy Administration

• Ensure company-wide compliance with applicable local, state, federal, and international employment laws across all entities and contractor networks, working directly with Crunchtime’s Legal counsel and external advisors.
• Oversee international employment documentation, statutory filings, and global privacy mandates (e.g., GDPR).
• Develop, localize, and maintain global employee handbooks, operational policies, and standard operating procedures.
• Partner with the CPO and Legal counsel on complex employee relations matters, investigations, documentation, performance improvement plans, and terminations.

Employee Lifecycle Mechanics & Enablement

• Oversee the mechanics of seamless onboarding, internal transfers, leaves of absence, promotions, and offboarding across all distributed and international locations.
• Manage the operational cadence of company-wide performance management cycles, review calibrations, and feedback delivery in alignment with the CPO’s talent philosophy.
• Support company-wide engagement, culture, recognition, and Diversity, Equity, Inclusion & Belonging (DEIB) initiatives by managing the logistics, tooling, and operational communications behind them.

Required Skills and Experience

• 10+ years of progressive experience in People Operations / HR Operations, with at least 5+ years directly leading people managers or specialized HR operations teams.
• Prior operational leadership experience in a high-growth, scaling technology or software enterprise.
• Deep hands-on experience with modern HRIS platforms (e.g., Rippling) and automated workflow integrations across IT & Finance systems.
• Strong background in payroll operations, compensation administration, benefits mechanics, and vendor contract oversight.
• Comprehensive understanding of multi-jurisdictional employment law, statutory compliance, and EOR/PEO operating models.
• Proven track record using workforce analytics and reporting to identify operational bottlenecks and inform talent decisions.
• Superior project management, cross-functional collaboration, and communication skills, with comfort presenting to executive stakeholders.
• Bachelor’s degree in Human Resources, Business Administration, or a related field; or equivalent practical experience.

Preferred Qualifications

• Professional HR certifications such as SPHR, SHRM-SCP, or GPHR.
• Hands-on experience executing People Operations integration for Mergers & Acquisitions (M&A), ideally within a high-velocity, private equity-backed, or rapidly scaling SaaS environment.
• Central/Eastern timezone
  
  

Essential Physical & Mental Requirements

• Prolonged periods of sitting at a desk.
• Prolonged periods of typing and working at a computer.
• Ability to listen and speak over the phone or Zoom/video calls.
• High level of mental concentration, analytical thinking, and focus.

Other Responsibilities

Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice.

Compensation & Transparency

The annual base compensation range for this position is $170,000-$200,000. The reasonably estimated total cash compensation (base + variable) range for this full-time position will be $195,500-230,000.

Actual compensation is based on factors unique to each candidate, including, but not limited to: job-related skills, qualifications, education, experience, and location.