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 rejection reasons and recurring selection barriers.

6. Onboarding and Launch Readiness

• Monitor accounts approaching onboarding and launch.
• Confirm that staffing, documentation, equipment, access, training, schedules, and client requirements are ready.
• Surface launch risks before they become client-facing issues.
• Coordinate resolution between responsible departments.
• Ensure accounts transition cleanly from pipeline management into normal account operations.

7. Post-Sales Pipeline Escalation Management

Serve as the first operational escalation point for pipeline-related issues. Examples include:

• Staffing delays
• Missing client requirements
• Candidate shortages
• Interview delays
• Client decision delays
• Incorrect Sales handoffs
• Compensation mismatches
• Training capacity concerns
• Onboarding blockers
• Ownership gaps
• System or CRM inaccuracies
• Accounts repeatedly moving backward in the pipeline
• Determine the appropriate owner, establish an action plan, and monitor the issue until resolution.

8. Pipeline Governance and Accountability

• Establish and enforce pipeline SLAs.
• Ensure teams update their respective pipeline stages consistently.
• Hold stakeholders accountable for overdue actions.
• Require clear next steps for every active account.
• Escalate repeated SLA breaches or operational blockers to leadership.
• Ensure pipeline meetings focus on decisions and corrective actions rather than status reporting alone.

9. Pipeline Reporting and Forecasting

Provide leadership with clear visibility into:

• Total active pipeline
• New accounts entering the pipeline
• Accounts staffed
• Accounts awaiting candidates
• Accounts awaiting client decisions
• Accounts scheduled for launch
• Aging by pipeline stage
• Average time spent per stage
• Staffing turnaround time
• Bottleneck trends
• At-risk accounts
• Projected launches
• Expected revenue activation
• Pipeline capacity and resource constraints
• Produce weekly and monthly pipeline health reports with clear recommendations and required leadership actions.

10. Process Improvement

• Continuously evaluate how accounts move through Wing's pipeline.
• Identify unnecessary steps, duplicated work, unclear ownership, and communication gaps.
• Design improved workflows and escalation protocols.
• Recommend automation opportunities.
• Partner with system owners to improve CRM and pipeline architecture.
• Standardize handoff requirements between departments.
• Document processes, SLAs, escalation paths, and ownership matrices.
• Measure whether process changes improve pipeline velocity and client experience.
• Prototype internal tools and workflow fixes using AI-assisted ("vibe coding") tooling, turning operational pain points into working proofs of concept.
• Partner with engineers and product managers to scope validated prototypes and see them through to fully built, production-ready tools.

11. Cross-Functional Coordination

Work closely with:

• Sales
• Customer Success
• Talent Acquisition
• Staffing
• Onboarding
• Training
• Operations
• Product or specialized service teams
• Finance and other support teams when required
• Ensure clean handoffs between departments and prevent accounts from being delayed because of unclear ownership or incomplete information.

Required Qualifications

• Startup and consulting experience - you've operated with startup speed and ambiguity, and bring the structured problem-solving instincts of a consulting background.
• Meticulous and detail-oriented - a naturally Type A operator who catches what others miss, with strong written and verbal communication skills.
• Operations background - strong experience in operations, program management, revenue operations, staffing operations, or customer success operations.
• Strong cross-functional judgment - demonstrated ability to manage complex workflows across multiple departments, making calls that touch sales, CSM, and operations without needing every decision escalated.
• Comfortable with high-volume, hands-on execution - a bias toward daily, hands-on execution over long-range planning; you'll be measured on whether requisitions stop falling through the cracks.
• Process and SLA discipline - comfortable defining SLAs, structuring workflows, managing escalations, and continuously optimizing how work moves through the pipeline.
• Excellent stakeholder management and follow-through - able to challenge teams constructively and drive accountability.
• Strong analytical and problem-solving skills - able to interpret operational data and convert findings into actionable recommendations.
• Technology fluency - experience using CRM, project management, reporting, and workflow management platforms; deep fluency with AI tools, and comfortable evaluating and rolling out new operational tools.
• Comfort operating at leadership altitude - you're the accountable owner in front of the CEO, COO, and Chief of Staff, not just executing tasks handed down from them.
• Able to travel to the Philippines as required.

Preferred Qualifications

• Experience in BPO, outsourcing, staffing, recruitment, SaaS, or other service-based organizations, especially with a similar post-sales handoff.
• Experience managing client implementation or fulfillment pipelines.
• Experience working across sales, operations, recruitment and customer success.
• Experience building or rolling out lightweight operational tooling - dashboards, CRM workflows, standup tools - at a growing company; familiarity with HubSpot, ClickUp, Power BI, or similar systems.
• Experience designing SLAs, dashboards, workflow automation, or operational governance.
• Exposure to APAC markets specifically.

Role Authority

The Head of Post-Sales Operations should have authority to:

• Request updates from all pipeline-owning teams.
• Challenge incomplete or inaccurate pipeline information.
• Escalate overdue actions.
• Convene stakeholders when an account becomes blocked.
• Recommend pipeline prioritization.
• Recommend process and SLA changes.
• Require clear owners and deadlines for pipeline issues.
• Escalate systemic concerns to the CEO, COO, CoS, Head of Sales, or relevant functional leader.

The role does not replace the functional ownership of Sales, Talent Acquisition, Staffing, Customer Success, Onboarding, or Training. Instead, it owns the movement, coordination, visibility, and overall health of the pipeline connecting these functions.

Reporting Structure

Reports to: CEO

Key stakeholders: C-Suite, Sales Leadership, Customer Success Leadership, Talent Acquisition, Staffing, Onboarding, Training, Finance, and Operations