Professional Services Lead

Core Cashless is currently looking for an AI-driven Professional Services Lead to join our team in the US!

We are now looking for an AI-Driven Professional Services Lead to modernize how we deliver, implement, and scale. The Professional Services Lead is a key position within the organization, serving as a player–coach who leads and develops the professional services team, directly contribute to the technical solution design and hands-on configuration, while also architecting AI-augmented delivery processes that eliminate repetitive manual work across services and engineering.

Here is a little window into our company: Core Cashless is the leading provider of innovative cashless payment solutions for the entertainment industry including amusement parks, waterparks, family entertainment centers, arcades, events and attractions. We offer a range of cutting-edge hardware/software solutions designed to integrate seamlessly with our customers’ infrastructure. From robust Point-of-Sale systems and self-service kiosks to handheld devices and access control solutions, our hardware is built to withstand the demands of high-volume environments.

The successful candidate will be based anywhere in the US, working in a remote work model with an expectation of travelling to see clients across North America up to 30% of the time!

What your day will look like:

AI-augmented Delivery Engine

• Build and maintain the information foundation to automate repeatable service tasks and streamline workflows
• Continuously refine service delivery methodology using automation insights
• Translate client workflows and pain points into AI-enabled products in partnership with the development team

Pre-Sales and Solution Design

• Lead discovery workshops and translate business needs into detailed solution design and configuration approach
• Lead labor estimates, scopes of work, Statements of Work (SOW), and proposal responses

Technical Implementation and Configuration

• Develop and execute customized implementation plans
• Own hands-on system configuration and solution setup
• Troubleshoot software, hardware, and integration challenges

Project and Delivery Leadership

• Develop and maintain detailed project plans for multiple implementation projects simultaneously, maintaining clear communication and exceptional service standards
• Ensure delivery occurs on time, within scope, and aligned with budget expectations
• Track risks, dependencies, and cross-functional blockers and escalate issues

Training, Knowledge Transfer and Documentation

• Create and manage high-quality presentations, training material, and implementation documentation for large internal and external audiences
• Conduct online and in-person client training and demos sessions
• Deliver structured handoffs to customer support teams
• Leverage AI to maintain and update documentation in real time

Team Leadership

• Assess professional services team and implement best practices

About You:

• 5+ years’ proven experience in Technical Implementation, Solution consulting, Professional Services or equivalent – preferably with cashless systems experience in the entertainment industry
• Hands-on experience with software configuration and hardware deployment
• Proven track record implementing automation within operational or delivery teams
• Ability to translate field insights into product improvements
• Ability to work in a fast-paced environment with new software/hardware updates regularly
• Self-starter mentality. Your instinct is to figure out what is next and move with or without explicit direction
• Highly organized and can prioritize when required to balance multiple clients and business needs
• Flexible, easily adaptable to change
• Excellent communication, presentation and training abilities, including active listening skills, to a wide variety of audiences
• Ability to Travel up to 30% of the time; this position requires travel in the United States, Canada, and outlying islands (with territory to expand over time)
• Travel arrangements may be made with short notice, and the person in this position should be able to cover daily travel expenses to be reimbursed
• A valid passport, driver's license, and the ability to rent a vehicle are required
• Fluent in English, both written and verbal, is essential
• Legally authorized to work in the US

Why Join Core Cashless?

At Core Cashless, you’ll have the opportunity to make a significant impact on our growth while working alongside a passionate team dedicated to transforming our industry. This is a key role, with ample opportunity for professional growth and direct impact on the company's success.

What We Offer:

• Competitive salary and bonus structure based on performance
• Health insurance, 401(k) with company match, and paid time off
• Opportunities for professional development and career advancement

If you're an AI-driven Professional Services Lead ready to take on this exciting challenge, we’d love to hear from you!

For further information about Core Cashless, please visit our website at https://corecashless.com

We thank all applicants for their interest; however, only those candidates selected for an interview will be contacted.