VA Engagement & Retention Partner

October 11

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Wing Assistant

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B2B • SaaS • Productivity

Wing Assistant is a company specializing in providing virtual assistant services to businesses worldwide. The company offers a wide range of services including general virtual assistant work, executive assistance, customer service, bookkeeping, and digital marketing. Wing Assistant aims to enhance productivity for startups and enterprise teams by delegating tasks to dedicated virtual assistants, reducing operational load, and enabling businesses to focus on core activities. Their services are accessible via a subscription model, providing flexible and cost-effective solutions compared to traditional hiring methods. Clients benefit from a dedicated assistant model where the assistant works solely for their business, gaining a deeper understanding of their processes over time.

501 - 1000 employees

🤝 B2B

☁️ SaaS

⚡ Productivity

💰 $2.1M Seed Round on 2022-03

📋 Description

• Conduct pre-start “pre-closing” calls with newly hired VAs to reinforce commitment, clarify expectations, and confirm readiness for deployment. • Facilitate pre-start check-ins and onboarding reminders to maintain engagement between offer acceptance and start date. • Design and execute 30-day and 60-day engagement touchpoints to assess adjustment, satisfaction, and early warning indicators. • Monitor new hire attendance, responsiveness, and communication patterns during ramp-up. • Identify and address potential back-out or attrition risks early, coordinating interventions with People Ops, Talent, and Operations teams. • Maintain detailed documentation of all engagement interactions, risk flags, and follow-up actions. • Collaborate with Training and Customer Success Enablement to ensure new hires receive the right support during their first client engagements. • Generate retention metrics and engagement health reports for leadership visibility. • Continuously improve engagement playbooks, call scripts, and ritual templates to enhance VA experience and retention outcomes.

🎯 Requirements

• Minimum 2–3 years of experience in HR, engagement, or account coordination — ideally within BPO, staffing, or remote workforce settings. • Strong communication and relationship-building skills; empathetic yet structured approach to candidate management. • Excellent follow-through and attention to detail. • Comfortable conducting high-volume calls or check-ins with professionalism and warmth. • Familiarity with employee engagement tools, CRMs, or HRIS systems. • Highly organized and capable of maintaining consistent communication cadences. • Background in candidate experience, onboarding, or retention programs is preferred. • Experience managing distributed or remote teams is preferred. • Data-oriented mindset with the ability to track and analyze retention trends is preferred.