Director of Operations

About Wing 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. About the Role 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. What You’ll Own Operational Leadership 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 Performance and Coaching Excellence 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 Workforce Health and Stability Partner with Workforce Management to actively manage absenteeism and attrition Build and execute corrective action plans to improve attendance and retention Training, Quality, and New Hire Success Co-own the Nesting Phase with Training and Quality leaders Implement controls to ensure new hires are effectively onboarded, supported, and performance-ready Hiring and Talent Partnerships Collaborate with Talent Acquisition through monthly immersion sessions Expose recruiters to top-performing Virtual Assistants to strengthen hiring blueprints Customer Experience and Retention 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 Employee Relations and Compliance Partner with HR on disciplinary actions and contract terminations for repeat infractions Ensure fair, consistent, and compliant handling of employee relations matters Payroll and Issue Resolution Work with Operations Managers and Payroll to resolve pay-related concerns and disputes efficiently What Success Looks Like 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 Key Metrics You’ll Be Accountable For Churn Rate with target to be defined Absenteeism and Attrition 8% Unplanned Absenteeism 40% Annualized Voluntary Attrition Team Quality Variance of plus or minus 5% SAT (Contractor Team Member Satisfaction) at 95% What We’re Looking For 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