Head of Post-Sales Operations

About the Role

Wing Assistant is hiring an exceptional, highly motivated individual to serve as the Head of Post-Sales Operations - the senior, leadership-adjacent owner of the post-sales pipeline.

This is the handoff that happens after a deal closes, spanning recruitment and staffing, onboarding, client activation, and early stage stabilization.

This is an operationally hands-on and execution-heavy partner working directly with the CEO, COO, CoS, and Head of Sales, accountable for keeping the post-sales pipeline continuously moving: identifying bottlenecks, enforcing timelines, coordinating cross-functional teams, and resolving process gaps that could delay revenue, staffing, onboarding or client activation.

Most of the actual territory sits downstream of the sales close and the role's scope spans sales, post-sales and CSM. This is not an administrative tracking role. The position is expected to actively manage the post-sales pipeline, challenge stalled items, drive accountability, escalate risks, and improve the underlying processes that keep the post-sales pipeline moving.

Key Responsibilities

1. Post-Sales Pipeline Management

- Own the daily operational management of Wing's active post-sales pipeline, from handoff through launch and early stage stabilization.

- Maintain full visibility into every account and requirement moving through the pipeline, with a clear status, owner, next action, and expected completion date for each item.

- Monitor accounts that are stalled, delayed, blocked, or at risk, and proactively follow up with the responsible team to move them forward before they become cancellations.

- Keep pipeline stages and CRM records accurate and current so they reflect the real operational status of every account, not just what's logged.

- Establish and enforce SLAs and a standard operating cadence, including daily standups and recurring reviews, so every stage of the pipeline moves on a predictable timeline.

- Build and maintain reporting and dashboards that give leadership real-time visibility into pipeline health, aging accounts, and forecasted launches.

2. Post-Sales Pipeline Health Monitoring

- Conduct daily reviews of pipeline movement and outstanding requirements.

- Identify aging accounts, stalled stages, capacity issues, and process bottlenecks.

- Flag accounts at risk of missing staffing or launch timelines.

- Monitor pipeline volume against available recruitment, staffing, onboarding, and operational capacity.

- Maintain clear visibility into what is entering, moving through, and exiting the post-sales pipeline.

3. Sales-to-Operations Handoff

- Review newly closed accounts and confirm that operational requirements are complete.

- Validate role requirements, client expectations, staffing needs, timelines, and special conditions.

- Identify incomplete, unrealistic, or unclear requirements before they create downstream delays.

- Coordinate with Sales when clarification or expectation resetting is required.

- Ensure specialized products or services follow the correct operational process.

4. Staffing and Candidate Pipeline Oversight

- Monitor recruitment and staffing progress against client requirements.

- Track candidate availability, endorsement, interviews, client selections, replacements, and pending decisions.

- Identify roles with insufficient candidate supply or prolonged staffing timelines.

- Coordinate with Talent Acquisition and Staffing leadership on priority requirements.

- Escalate accounts requiring intervention, sourcing adjustments, compensation review, or expectation management.

5. Client Selection and Decision Management

- Track candidates presented to clients and outstanding client decisions.

- Ensure follow-ups occur within established timelines.

- Identify accounts where client responsiveness is delaying fulfillment.

- Coordinate with CSMs, OBS, Sales, or account owners when client intervention is required.

- Maintain visibility into candidate re