AI Implementation Associate

About Railbookers:

At Railbookers, we believe that the journey is just as fulfilling as the destination. Life onboard is full of opportunities, new experiences, and rewarding relationships.

We’re a team of diverse, talented people from around the world. As we continue to expand internationally, we strive to ensure that our culture remains alive and well -that we remain aligned and engaged. Global movements don’t spring from one individual. It takes an entire team to make an impact and do something BIG. At Railbookers, we encourage every employee to identify areas of opportunity within the organization.  

Every single person at Railbookers has a passion for travel, which explains why we’re so avid about encouraging our customers to get out and discover the world for themselves. Most importantly, we embolden you to be yourself and enjoy the work you do on a daily basis. We like having a great time at work, not just outside of it.


Job Purpose:

Railbookers Group, the world’s leading independent rail vacation provider, is driving a company-wide AI transformation. The AI Implementation Associate will primarily focus on driving AI adoption, defining best practices, and integrating AI into business operations. You will be responsible for ensuring every department and role within the organization leverages AI to become more productive, strategic, and customer focused. This role bridges strategy and execution, deploying AI solutions that streamline operations, elevate decision-making, and place the customer experience at the center of every initiative.


Key Responsibilities:

• AI Strategy Execution - Drive the rollout of Railbookers’ AI roadmap across all functions (Sales, Marketing, Operations, Rail, Finance, HR, QC, Customer Service), ensuring measurable improvements in productivity and customer satisfaction.
• AI Agent Development - Lead the creation, training, and continuous improvement of department-specific AI agents to support quoting, booking, quality control, marketing content, HR workflows, and financial analysis.
• Operational Integration - Embed AI tools into day-to-day workflows to simplify processes, reduce errors, and free up staff for higher-value, customer-centric activities.
• Data Integration - Partner with Data Engineering to leverage Railbookers’ Data Lake and Knowledge Graph, ensuring AI systems are powered by accurate, centralized, and high-quality data.
• Human x AI Collaboration - Establish frameworks, training, and change-management initiatives so staff across all departments can confidently and effectively collaborate with AI tools.
• Performance Measurement - Define, monitor, and report on KPIs that demonstrate clear business impact, including efficiency gains, higher conversion rates, reduced turnaround times, and enhanced customer outcomes.
• AI Governance & Compliance - Maintain standards for ethical AI use, compliance with data privacy laws, and adherence to corporate governance policies.
• Innovation & Continuous Improvement - Proactively identify new AI use cases, pilot emerging technologies, and scale successful solutions across the company.
• Cross-Functional Leadership - Collaborate with department leaders to prioritize AI opportunities, drive adoption, and ensure solutions align with both strategic goals and frontline needs.
• Vendor & Partner Management - Manage relationships with external AI partners, vendors, and consultants to accelerate innovation and maintain competitive advantage.

• Bachelor’s degree in Business, Computer Science, Data/Business Analytics, or equivalent practical experience.
• 3+ years of experience leading digital transformation, automation, or AI-driven initiatives, with at least 2 years in a leadership or management role.
• Proven success introducing and scaling AI tools (e.g., LLMs, copilots, workflow automation, customer service/chatbots, knowledge assistants) across multiple business functions.
• Strong understanding of how AI integrates with enterprise systems, workflows, and data platforms, rather than deep model development.
• Demonstrated ability to drive change management and adoption programs, ensuring staff at all levels feel confident using AI tools.
• Excellent communication and facilitation skills, able to simplify technical concepts into clear business value for leadership and frontline staff.
• Experience creating AI best practices, governance frameworks, and training programs for business users.
• Strong project management and prioritization skills; able to balance multiple initiatives and deliver measurable business outcomes.
• Familiarity with AI ethics, compliance, and data privacy considerations in enterprise settings.

Preferred Experience: 

• Background in retail, travel, hospitality, or e-commerce industries.
• Track record of delivering AI solutions that generate measurable ROI.
• Experience with customer-facing AI applications such as conversational AI, personalization engines, or recommendation systems.

Measures of Success:

• Adoption and active use of AI agents across all departments.
• Reduction in manual errors, delays, and QC turnaround times.
• Higher quote-to-booking conversion rates driven by AI-enabled efficiencies.
• Increased employee productivity and satisfaction with AI support tools.
• Demonstrable cost savings, revenue uplift, or margin improvement from AI initiatives.
• Reinforcement of Railbookers’ position as the global leader in AI-powered rail vacation booking.

What we Offer:  

• Work from Home  
• Generous PTO Package  
• Bonus and Incentive Plans  
• Medical, Dental, and Vision Insurance Including Optional HSA, Gym Membership Contributions and Healthy Actions incentive (sponsored by Cigna)  
• Employee Assistance Program  
• Short-term/Long Term disability Plan  
• Employer sponsored Life Insurance  
• Employer-Matched 401(k)  
• Familiarization Trips (Get paid to experience our vacations!)  
• Employee and Family/Friend Travel Discounts  
• Corporate Discounts through Working Advantage  
• Employee Referral Bonus  
• Cross-Departmental and Advanced Training Opportunities  
• Anniversary, Birthday, and Recognition Perks  
• Years of Service Awards  
• Annual Reimbursements for Home Office (office expenses, phone, internet)