Head of Talent Operations

About the Role

Sienna Charles is seeking a highly organized, systems-minded, and data-driven Head of Talent Operations to build and lead every aspect of our hiring, onboarding, training, and employee development infrastructure.

This is not a traditional HR role. We are looking for someone who views recruiting, onboarding, and employee success as operational systems that can be measured, optimized, and continuously improved.

You will own the entire employee lifecycle—from identifying exceptional candidates to ensuring every new hire is fully trained, productive, and meeting performance expectations. You’ll build scalable hiring processes, implement best-in-class recruiting and onboarding systems, create role-specific training programs, and partner closely with department leaders to develop high-performing teams.

The ideal candidate is an equal parts recruiter, project manager, trainer, process builder, and operator. They thrive on creating structure, love data, embrace technology and AI, and are relentless about raising standards.

Responsibilities

Talent Acquisition & Recruiting Operations

• Own the end-to-end recruiting process across all departments.
• Develop and maintain recruiting pipelines for recurring and future hiring needs.
• Create and continuously improve hiring workflows and recruiting systems.
• Write and refine job descriptions, interview guides, and hiring scorecards.
• Manage candidate communications and interview scheduling.
• Conduct structured reference and background checks.
• Administer and evaluate assessments and skills testing.
• Partner with department leaders to define hiring needs and success profiles.
• Continuously improve hiring quality, speed, and candidate experience.

Hiring Systems & Process Design

Build a scalable hiring infrastructure by creating and maintaining:

• Hiring playbooks
• Recruiting SOPs
• Interview scorecards
• Competency frameworks
• Assessment libraries
• Candidate evaluation templates
• Hiring dashboards
• Offer letter templates
• Recruiting documentation
• Talent databases

Develop repeatable processes that allow the company to scale hiring efficiently while maintaining exceptionally high standards.

Employee Onboarding

Own the complete onboarding experience.

Design structured onboarding programs that ensure every employee understands:

• Company culture
• Service philosophy
• Performance expectations
• Communication standards
• Systems and technology
• Department workflows
• Documentation standards
• Client experience expectations

Coordinate all onboarding logistics, including:

• Equipment and software provisioning
• Training schedules
• Account setup
• Introductions
• Documentation
• System access

Lead daily onboarding check-ins during each employee’s first two weeks to reinforce expectations, answer questions, identify challenges early, and ensure a successful transition into the company.

Training & Learning

Develop role-specific onboarding and training programs for every department.

Examples include:

• Executive Assistants
• Member Experience
• Sales
• Operations
• Marketing
• Finance
• Concierge Services

Create:

• 30/60/90-day training plans
• Daily onboarding schedules
• Learning milestones
• SOP libraries
• Knowledge assessments
• Certification checklists
• Training documentation
• Video libraries

Continuously improve training based on employee feedback and performance outcomes.

Performance Management

Partner with department leaders to ensure new hires are successful beyond onboarding.

Develop and manage:

• Role-specific KPIs
• 30-, 60-, and 90-day reviews
• Performance scorecards
• Accountability meetings
• Coaching plans
• Performance improvement plans
• Progress tracking dashboards

Identify performance gaps early and work with managers to provide coaching and support.

HR Operations

Maintain and continuously improve core people operations, including:

• Employee handbook
• Company policies
• Performance review processes
• New hire documentation
• Compliance documentation
• Organizational charts
• Career path frameworks
• Internal communication resources

Support leadership with organizational planning and workforce development initiatives.

Technology & Automation

Build modern, technology-driven HR systems.

Identify, implement, and optimize tools for:

• Applicant Tracking Systems (ATS)
• HRIS platforms
• Learning Management Systems (LMS)
• Assessment platforms
• AI-assisted recruiting
• Workflow automation
• Reporting dashboards
• Digital onboarding
• Documentation management

Continuously evaluate opportunities to automate repetitive administrative work and improve efficiency.

Data & Analytics

Use data to improve hiring and employee success.

Track and report on key metrics including:

Recruiting

• Time-to-fill
• Time-to-hire
• Source effectiveness
• Offer acceptance rate
• Candidate conversion rates
• Cost per hire

Onboarding

• Time-to-productivity
• Training completion
• New hire satisfaction
• Early turnover
• Ramp-up success

Performance

• 90-day success rate
• KPI achievement
• Employee retention
• Manager feedback
• Training effectiveness

Provide leadership with actionable insights and recommendations to improve hiring quality, employee performance, and organizational effectiveness.

Qualifications

• 5+ years of experience in Talent Operations, People Operations, Recruiting Operations, HR Operations, or a related field.
• Experience building hiring, onboarding, and training systems from the ground up.
• Strong project management and organizational skills.
• Exceptional written and verbal communication abilities.
• Highly analytical and comfortable using data to drive decisions.
• Experience implementing HR technology and workflow automation.
• Strong understanding of recruiting best practices and structured interviewing.
• Ability to manage multiple hiring processes simultaneously in a fast-paced environment.
• Naturally process-oriented with meticulous attention to detail.
• High level of ownership, accountability, and follow-through.
• Passion for building scalable systems that improve organizational performance.

Preferred Experience

• Experience in hospitality, luxury services, concierge, consulting, startups, or other high-touch client service environments.
• Experience creating learning and development programs.
• Familiarity with AI tools for recruiting, documentation, and process automation.
• Experience with ATS, HRIS, LMS, and project management platforms.
• Experience supporting rapid organizational growth.

What Success Looks Like

Within your first year, you will have:

• Built a world-class recruiting operation with standardized hiring processes across every department.
• Reduced time-to-hire while improving hiring quality.
• Developed comprehensive onboarding programs for every role.
• Implemented structured 30/60/90-day training and performance plans.
• Established KPI dashboards and reporting for hiring, onboarding, and employee success.
• Created a repeatable talent operating system that enables Sienna Charles to scale while preserving our culture, service standards, and commitment to excellence.