Team Success Supervisor
About the job
- At least 3–5 years of experience in a supervisory role, with a strong background in managing and coaching teams.
- Ability to guide and motivate team members to help them achieve goals and grow in their roles.
- Broad understanding of various industries and ability to learn new fields quickly to guide a diverse client base.
- Verbal and written communication skills for delivering clear, constructive feedback.
- Experience with remote work tools and platforms such as Discord, G Suite, and Asana, and with managing teams across time zones.
- Availability to participate in in-person meetings with the core team 2–3 times per week.
- Analytical approach to addressing challenges and improving team processes.
- Fast, reliable internet connection and reliable electricity.
- Professional microphone headset or functional computer microphone.
- Fast, responsive computer.
- Clean, professional background and audio environment for video calls with customers.
- Manage a team of Virtual Assistants, fostering a positive, productive, and engaging work culture and ensuring each team member understands their goals and has the resources needed to succeed.
- Provide tailored coaching to Virtual Assistants based on their experience and industry needs; meet regularly with each to discuss performance, set objectives, and provide actionable feedback for growth.
- Attend 2–3 in-person collaborative sessions per week with the core team to strategize, discuss team progress, and plan initiatives to improve service delivery continuously.
- Use knowledge of various industries to support Virtual Assistants in delivering industry-specific solutions, addressing diverse client needs, and adapting to new sectors as required.
- Set measurable performance goals, track team progress, identify improvement areas, conduct regular performance evaluations, and maintain high standards.
- Serve as the first point of contact for escalated issues; resolve client concerns, mitigate risks, and implement solutions to improve team efficiency.
- Encourage Virtual Assistants to share insights and identify areas for personal and professional development; develop initiatives that promote ongoing learning and growth within the team.
About the company
Wing Assistant provides virtual assistant services for businesses, offering dedicated virtual assistants that work remotely on a full-time or part-time basis through a subscription model. Clients hire VAs who handle administrative tasks such as invoicing, payment tracking, and expense recording, while gaining complimentary access to the Wing Task Workspace App for communication, task management, file sharing, and screen recording. The service works by assigning a dedicated VA and, if needed, a Customer Success Manager plus thorough training for assistants to ensure consistent quality. This differentiates Wing Assistant through a strong emphasis on customer support and investment in VA training, with pricing tied to service level and hours required. The company’s goal is to help businesses run more efficiently by providing reliable, scalable administrative support via licensed remote assistants.
Company Size
1,001-5,000
Company Stage
Seed
Total Funding
$2.2M
Headquarters
Berkeley, California
Founded
2018
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Simplify's Take
What believers are saying
- Wing reported 210% annualized growth after $1.4 million revenue-based financing in 2023.
- Its 2026 careers pages show active hiring, suggesting demand and ongoing operational expansion.
- 2026 content marketing around outsourcing and AI services strengthens lead generation against smaller rivals.
What critics are saying
- Wing still relies on low-margin labor subscriptions, exposing it to price wars and churn.
- 2026 job posts tie Wing to M32 AI, signaling uncertain strategic drift from core services.
- The mandatory arbitration terms and security complaints raise client-trust risk before 2027 renewals.
What makes Wing Assistant unique
- Wing bundles dedicated virtual assistants with customer success and task-workspace software.
- Its 2026 hiring pages emphasize global remote coverage across hundreds of open roles.
- Wing markets specialized vertical support, including medical scribing and customer service outsourcing guides.
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Benefits
- Performance Bonus
- Job Security
- Paid Training
- Inclusive Culture
- Upskilling Opportunities
- Remote Work Options
- Exceptionally Supportive Team
- Opportunities for Career Growth
- Company Social Events
- Holiday & Overtime Pay