Sales Representative – US & Canada (Casino Management Systems)

Win Systems International Holdings Inc.

38d • Remote

About The Position

Win Systems is a leading technology supplier with 25 years of experience providing management solutions, electronic roulette, and slot machines to the casino and lottery industries.

With its best-in-class casino management systems, gaming machines, and an easily integrated end-to-end service, Win Systems is the go-to supplier for all gaming requirements.

Win Systems has expanded to operate in over 60 countries worldwide, offering a multi-channel service across hundreds of venues of varying sizes and multiple regulatory jurisdictions. Win Systems aims to become the trendsetter for the gaming technology sector, and we are certain our solutions will shape the future of the casino environment

The role is responsible for managing the full consultative sales cycle, building long-term customer relationships, and positioning the company as a trusted technology partner within the gaming industry. The role focuses on selling enterprise-level SaaS Casino Management Systems to casino operators and gaming organizations.

The ideal candidate has proven experience in SaaS software sales, preferably within the gaming, casino, or hospitality technology sector, and a strong ability to manage complex, consultative sales cycles involving multiple stakeholders.

LOCATION: USA. We have offices in Miami, but you can work remotely if you live in a different state in the USA.

Requirements

• Bachelor’s degree in Business Administration, Marketing, Information Technology, Engineering, or a related field
• Proven experience in SaaS software sales (required)
• Experience selling enterprise or complex software solutions with long sales cycles
• Demonstrated ability to manage multiple stakeholders and decision-makers in B2B environments
• Experience using CRM systems and structured sales methodologies
• Willingness and ability to travel extensively (50–75%), with frequent domestic and international trips.
• Ability to work effectively in a globally integrated, cross-functional team, collaborating with operations, development, and pre-sales teams.
• Results-driven sales mindset, motivated by a competitive compensation structure combining equipment sales and recurring software revenue.
• High degree of versatility and adaptability, with a team-first attitude and willingness to contribute beyond a traditional sales role when needed.

Nice To Haves

• Prior exposure to the casino, gaming, or hospitality technology sector is highly preferred

Responsibilities

• Identify, develop, and close new business opportunities for Casino Management System SaaS solutions
• Manage the full sales cycle from lead generation and qualification through negotiation and contract execution
• Build strong relationships with casino executives, operational leaders, and technology stakeholders
• Delivering compelling product presentations, demonstrations, and solution proposals aligned with client's business needs
• Understand casino operational workflows and translate them into tailored software solutions
• Coordinate with Pre-Sales, Product, Legal, and Customer Success teams to support deal advancement and closing
• Maintain accurate pipeline management, forecasting, and CRM documentation
• Represent the company at industry events, trade shows, and client meetings as required

Benefits

• Indefinite-term contract.
• Comprehensive health insurance and 401K.
• Paid time off (PTO).
• Team-first culture – collaborative, globally integrated sales and operations teams
• Work with a growing company – join a solid, competitive product in the land-based casino industry.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level