Sr Associate Technical Support Analyst - Adaptive Planning AI, ML & Application Support (Monday-Friday, 12pm to 9 pm)

Your work days are brighter here. We’re obsessed with making hard work pay off, for our people, our customers, and the world around us. As a Fortune 500 company and a leading AI platform for managing people, money, and agents, we’re shaping the future of work so teams can reach their potential and focus on what matters most. The minute you join, you’ll feel it. Not just in the products we build, but in how we show up for each other. Our culture is rooted in integrity, empathy, and shared enthusiasm. We’re in this together, tackling big challenges with bold ideas and genuine care. We look for curious minds and courageous collaborators who bring sun-drenched optimism and drive. Whether you're building smarter solutions, supporting customers, or creating a space where everyone belongs, you’ll do meaningful work with Workmates who’ve got your back. In return, we’ll give you the trust to take risks, the tools to grow, the skills to develop and the support of a company invested in you for the long haul. So, if you want to inspire a brighter work day for everyone, including yourself, you’ve found a match in Workday, and we hope to be a match for you too. About the Team At Workday, we bring technical rigor, customer empathy, and a spirit of fun to enterprise software. Our support team underpins operational excellence across Workday's digital experience, ensuring top-tier service for our core applications while also supporting our growing AI/ML platform and Agent Factory initiative. Within this ecosystem, the Workday Adaptive Planning Support team plays a critical role in empowering our customers to build agile, data-driven financial strategies. We partner directly with product and technology teams to eliminate bottlenecks, maintain high platform availability, and ensure system reliability—focusing heavily on our robust Planning features and functionality, alongside our next-generation AI workflows for our global customer base. About the Role We are seeking a customer-focused Senior Associate Support Analys t to drive case and incident resolution, issue analysis, research, and investigation, and operational optimization across Workday’s Adaptive Planning platform and our autonomous AI agent workflows. In this high-visibility role, you will bridge the gap between traditional SaaS troubleshooting and cutting-edge AI operations. You will manage a case queue of varying complexity, including customer escalations within strict SLAs while partnering directly with Support Engineers and Product Management teams to inform feature iteration and product fixes and optimizations.  The key parts of this role will involve your core focus on becoming an expert at the Adaptive Planning platform, alongside evaluating AI quality : reviewing chat histories and AI responses to spot mistakes, figure out why they happened, and turn those insights into simple improvements that make the AI clearer, smarter, and more reliable.  Location & Shift • Location : This position is based in the Workday Heredia, Costa Rica office.  • Hybrid Work : Candidates will be expected to work from the office at least 50% of the time. • Hours : Typical shift will be from Monday-Friday, 12pm to 9 pm available • On-Call : Participation in an on-call rotation is required to provide after-hours support when needed. Key Responsibilities • Core Planning and Reporting Troubleshooting: Troubleshoot with customers on cases to resolve reported issues with their financial data, reporting, and/or financial integrations. • Enterprise SaaS & Functional Domain Knowledge: Develop a foundational understanding of enterprise SaaS workflows (including Finance, HR, and Payroll) to assist in validating AI logic and verifying expected system behavior. • AI Concepts : Review AI chat logs and execu