Outbound Cold Caller
About the job
- 1–3+ years of experience in cold calling, sales development representative work, lead generation, or outbound sales.
- Comfort making 50–100+ outbound calls daily.
- Experience using LinkedIn for prospecting.
- Familiarity with email outreach tools and customer relationship management systems.
- Strong communication and persuasion skills.
- Resilience and comfort handling rejection.
- Research skills to identify appropriate prospects.
- Self-motivation and a results-driven approach.
- Conduct high-volume outbound cold calls to prospective clients.
- Identify and qualify potential leads and decision-makers.
- Schedule meetings for the sales team with qualified prospects.
- Execute multichannel outreach campaigns, including cold calling, LinkedIn prospecting, email marketing, and SMS outreach.
- Research target accounts and personalize outreach strategies.
- Meet or exceed outreach and meeting quotas.
- Maintain accurate records of outreach activities in the customer relationship management system.
- Collaborate with the sales team to improve messaging and conversion.
- Experiment with creative prospecting techniques.
- A hunter mentality and enjoyment of outbound sales and prospecting.
- Creativity in outreach strategies.
- Competitiveness and motivation to hit targets.
- Ability to thrive in a fast-paced sales environment.
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
Growth & Insights and Company News
6 month growth
0%1 year growth
0%2 year growth
0%Wing Assistant, an Irvine, Calif. – based platform enabling companies to find remote talent for recurring work, raised $2.1m in seed funding. Backers included Surface Ventures, Brookstone Venture Capitaland UC BerkeleySkyDeck as well as angel investors. Co-founded by Karan Kanwar, CEO, Martin Gomez, COO, Saideep Gupta, CTO, and Roland Polzin, CMO, Wing Assistant provides business [] The post Wing Assistant Raises $2.1M in Seed Funding appeared first on FinSMEs.
Wing AI is partnering with KiwiBot to develop robotic delivery services.
Wing AI is partnering with KiwiBot to develop robotic delivery services.