Software Sales Representative

Software Sales Representative

WingStack.ai | Remote

Company Description

WingStack.ai is a modern software platform built specifically for the private aviation industry. Our platform brings charter brokers, operators, trip planners, and passengers together in one streamlined system, simplifying how private aviation businesses manage their daily operations.

From aircraft sourcing and charter quoting to CRM, trip management, payments, and real-time flight tracking, WingStack eliminates the need for disconnected tools and manual processes.

Our mission is simple: make private aviation easier, faster, and more efficient through technology.

Role Description

WingStack.ai is seeking a motivated and results-driven Software Sales Representative with a strong understanding of private aviation and charter brokerage operations to help expand our growing user base.

This is a remote position focused on introducing WingStack to charter brokers, charter sales professionals, aircraft operators, and other aviation businesses, demonstrating the platform, and converting prospective customers into active users.

The ideal candidate understands how the private charter industry operates, including aircraft sourcing, charter quoting, broker-operator relationships, and trip coordination. We are looking for someone who can confidently engage with aviation professionals, understand their challenges, and demonstrate how WingStack can improve their daily workflows.

This is a hands-on sales role focused on outreach, relationship building, product demonstrations, and user acquisition.

Key Responsibilities

Sales & Business Development

• Identify and engage charter brokers, charter sales teams, aircraft operators, and aviation businesses that could benefit from WingStack.
• Conduct outbound prospecting through phone calls, emails, LinkedIn, and industry relationships.
• Build and maintain relationships with charter brokers and other private aviation professionals.
• Demonstrate WingStack's capabilities, including aircraft sourcing, quoting, CRM, trip management, and operational tools.
• Understand prospective customers' existing workflows and identify opportunities where WingStack can improve efficiency.
• Convert prospective customers into registered and active platform users.
• Manage the sales process from initial outreach through product demonstration and onboarding.
• Maintain accurate records of leads, outreach activities, demonstrations, and user conversions.
• Develop referral opportunities and expand WingStack's presence within the private aviation community.

Customer Onboarding & Growth

• Assist new users with account setup and initial platform onboarding.
• Help charter brokers understand how to incorporate WingStack into their existing sales and operational workflows.
• Encourage platform adoption and continued engagement.
• Gather feedback from aviation professionals and communicate opportunities for product improvements to the development team.
• Identify opportunities to introduce WingStack to additional brokers, sales teams, and operators.
• Collaborate with leadership on user acquisition strategies and market expansion.

Qualifications

• Experience in private aviation, charter brokerage, or charter sales is strongly preferred.
• Strong understanding of the Part 135 charter industry and the relationship between charter brokers and aircraft operators.
• Familiarity with aircraft sourcing, charter quoting, trip planning, and broker workflows.
• Existing relationships within the private aviation industry are highly desirable.
• Previous experience in software sales, SaaS sales, business development, or customer acquisition preferred.
• Ability to communicate confidently with charter brokers, sales professionals, and aircraft operators.
• Comfortable conducting outbound sales calls, prospecting, and virtual product demonstrations.
• Familiarity with aviation quoting platforms, CRM systems, and charter management software is a plus.
• Strong communication, relationship-building, and presentation skills.
• Self-motivated, organized, and capable of working independently in a remote environment.
• Ability to learn new technology quickly and clearly explain its value to aviation professionals.
• Results-oriented mindset with strong follow-through and attention to detail.

Why Join WingStack.ai?

WingStack is developing technology designed to modernize how private aviation professionals conduct business. Our goal is to simplify charter sales and operations by bringing the tools brokers and operators rely on into one platform.

As part of our growing team, you'll work directly with aviation professionals, help shape how our platform is adopted across the industry, and play an important role in expanding WingStack's presence in the private aviation market.

We're looking for someone who already understands the charter industry, enjoys building relationships, and is excited about introducing innovative technology to aviation professionals.

• If you have a background in private aviation or charter sales and are passionate about technology, business development, and helping aviation professionals work more efficiently, we'd love to hear from you.