Director of Operations

Wing is one of the world’s largest virtual talent companies, venture-backed and headquartered in San Francisco. We help businesses build, scale, and manage world-class remote teams through a combination of operational excellence, technology, and deep people expertise. At Wing, we believe strong operations are the backbone of exceptional customer and contractor experiences.

We are hiring a Director of Operations to lead the execution, performance, and day-to-day delivery of our Operations organization. This role is accountable for ensuring our Operations Managers and Team Supervisors consistently deliver high-quality outcomes while upholding Wing’s core values.

The Director of Operations plays a critical role in translating strategy into execution by building bridge plans, strengthening frontline leadership, improving performance metrics, and driving cross-functional alignment with Workforce Management, Training, Quality, HR, Talent Acquisition, Payroll, and Customer Success.

This is a hands-on leadership role for someone who thrives in fast-moving environments, leads through data and coaching, and balances accountability with a strong people-first culture.

Own the output, delivery, and execution of day-to-day operations across multiple teams

Lead, coach, and develop Operations Managers and Team Supervisors

Run regular leadership huddles to align on priorities, risks, and initiatives

Partner with Operations Managers and Supervisors to conduct triads and quad jacks

Ensure high-quality coaching for bottom-quartile performers based on stack-ranked scorecards

Execute Performance Improvement Plans (PIPs) while reinforcing Wing’s core values through recognition and rewards

Partner with Workforce Management to actively manage absenteeism and attrition

Build and execute corrective action plans to improve attendance and retention

Co-own the Nesting Phase with Training and Quality leaders

Implement controls to ensure new hires are effectively onboarded, supported, and performance-ready

Collaborate with Talent Acquisition through monthly immersion sessions

Expose recruiters to top-performing Virtual Assistants to strengthen hiring blueprints

Work closely with Customer Success to review churn data on a weekly basis

Develop and execute bridge plans to reduce churn and improve long-term retention

Partner with HR on disciplinary actions and contract terminations for repeat infractions

Ensure fair, consistent, and compliant handling of employee relations matters

Work with Operations Managers and Payroll to resolve pay-related concerns and disputes efficiently

Strong alignment and accountability across Operations leadership

Improved performance and coaching outcomes for underperforming team members

Controlled absenteeism and attrition through proactive workforce planning

Smooth onboarding and nesting experiences for new hires

Actionable churn reduction plans with measurable impact

Timely resolution of performance, payroll, and employee relations issues

Churn Rate with target to be defined

8% Unplanned Absenteeism

40% Annualized Voluntary Attrition

Team Quality Variance of plus or minus 5%

SAT (Contractor Team Member Satisfaction) at 95%

Minimum of 5 years of experience in a senior operations leadership role

Background in BPO and/or Virtual Assistant environments

Proven ability to lead large, multi-layered teams

Strong execution, coaching, and cross-functional collaboration skills

Data-driven approach to performance management and operational improvement

Ability to build structure, clarity, and momentum in complex operations