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Salary
≈ $9k – $23k per year (Estimated)
Location
Remote (United States, South Africa)also open in Argentina
Employment
Full-Time

Confirmed on the employer's own hiring board on Oct 19, 2026. First seen by Alion on Sep 17, 2026. Wing Assistant scores B on the Alion truth index.

Overview
Company
Impact
Profile match
Wing Assistant is a remote staffing company that provides small businesses, startups, executives and enterprises with dedicated full-time remote assistants for recurring work such as executive assistance, social media management, data entry, outbound sales calling and marketing. Most of its assistants are recruited in the Philippines, with hiring also in Latin America, for roles such as digital marketing account managers, social media specialists and automation developers. The company is headquartered in Berkeley, California, United States.

About the Role

We are seeking a motivated and experienced Account Executive - AI Agents to join our team in South Africa. This is a unique opportunity to work remotely while engaging with US small and medium business owners. You will be responsible for driving our sales process from discovery to close, ensuring a smooth transition for our clients as they adopt our innovative AI solutions.

The ideal candidate is a proven B2B SaaS closer with a track record of successfully managing the entire sales cycle. You will be expected to demonstrate confidence and expertise when running live demos and discussing ROI, while also maintaining a disciplined approach to CRM management.

This position is perfect for someone who is self-directed, commercially sharp, and obsessed with hitting their numbers. If you thrive in a fast-paced environment and have the ability to close deals efficiently, we want to hear from you!

Responsibilities

  • Own the full sales cycle from discovery through to contract signing and first payment.
  • Conduct live demos and present our AI solutions to potential clients.
  • Handle objections and effectively communicate the value and ROI of our offerings.
  • Close deals with an average MRR of $300-$650+ and short sales cycles.
  • Maintain daily follow-ups with leads to ensure a high close rate.
  • Structure terms of deals and hold pricing rather than discounting immediately.
  • Track and manage sales activities in CRM with discipline and accuracy.
  • Communicate confidently and peer-level with US SMB owners.
  • Run several live demos per day, demonstrating product capabilities effectively.
  • Collaborate with the sales and marketing teams to optimize strategies and processes.

Requirements

  • Proven experience in B2B SaaS sales with a strong closing record.
  • Ability to manage the full sales cycle independently.
  • Exceptional communication skills in written English.
  • Experience with CRM systems and maintaining accurate records.
  • Self-directed and motivated with a results-oriented mindset.
  • Strong negotiation skills and ability to handle objections proficiently.
  • Ability to engage with SMB owners confidently and professionally.
  • Disciplined approach to daily follow-ups and lead management.

Nice to Have

  • Experience in selling AI or tech-related solutions.
  • Familiarity with US SMB market dynamics.
  • History of exceeding sales quotas and performance metrics.
  • Strong understanding of ROI calculations and financial discussions.
  • Experience running product demos in a virtual setting.

Benefits

  • Full-time remote position with flexibility to work from anywhere in South Africa.
  • Engaging company culture focused on innovation and performance.
  • Competitive base salary plus commission structure.
  • Opportunities for professional development and career advancement.
  • Collaborative team environment with a focus on results.
  • Access to cutting-edge AI technology and resources.
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