Sr Associate Customer 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 Analyst 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 execution outputs to spot incorrect answers, hallucinations, or misunderstandings. Document findings and recurring patterns to support senior team members and engineering in refining prompt logic.
• Technical Troubleshooting: Utilize established troubleshooting playbooks, diagnostic dashboards, and monitoring tools to reproduce reported issues, gather relevant logs, and isolate basic software bugs.
• Technical Acumen: Run basic database queries (SQL), review application logs, and inspect API payloads to verify data flow, check system state, and assist with basic cloud workflow troubleshooting.
• Customer Advocacy: Monitor and respond to incoming support queues, maintain strict SLA commitments, and communicate clearly with users. Provide empathetic, plain-language updates to customers while issues are being investigated.
• Incident & Queue Management: Perform initial queue triage, classify issue severity, and route high-impact (P1) incidents to senior analysts or engineering teams using defined escalation pathways. Participate in weekend and holiday on-call rotations with team support.

About You

Basic Qualifications 

• Work Experience: Minimum 1 year of experience in technical support, customer success, IT operations, software administration, or a technical internship.

• Technical & System Operations:

  • Minimum 1 year of hands-on experience using public cloud platforms (AWS, GCP, or Azure).

  • Minimum 1 year of experience accessing and reviewing system logs or monitoring tools (e.g., Datadog, Splunk, or cloud-native log viewers).

• AI/LLM Familiarity: Experience using, testing, or reviewing Large Language Model (LLM) outputs or prompt structures.

• Queue Management: Minimum 1 year of experience managing ticketing systems, support queues, or prioritized task workflows.

Preferred Qualifications

• Bachelor’s degree in Business Administration, Finance, Human Resources, Management Information Systems (MIS), Data Analytics, Computer Science, Engineering, or a related field (or equivalent practical work experience in software support or system administration).

• Demonstrated interest in evaluating conversational AI performance, quality metrics, and output accuracy.

• Comfortable working with software where there may be some ambiguity in determining solutions and next steps.

• Ability to clearly articulate technical concepts through written and verbal communication.

• Strong organizational skills and adaptability to learn complex, evolving technical systems.

• Proficient in Microsoft Excel/Google Workspace.

• Had previous experience or knowledge of finance and/or financial planning software applications or integrations

Our Approach to Flexible Work
 

With Flex Work, we’re combining the best of both worlds: in-person time and remote. Our approach enables our teams to deepen connections, maintain a strong community, and do their best work. We know that flexibility can take shape in many ways, so rather than a number of required days in-office each week, we simply spend at least half (50%) of our time each quarter in the office or in the field with our customers, prospects, and partners (depending on role). This means you'll have the freedom to create a flexible schedule that caters to your business, team, and personal needs, while being intentional to make the most of time spent together. Those in our remote "home office" roles also have the opportunity to come together in our offices for important moments that matter.

Workday is committed to providing reasonable accommodations for qualified individuals during our application process, in order to perform one or more essential functions of their job, as well as regarding the use of AI tools for employment decision-making to any degree. Please see below for more details including how to request an accommodation as a qualified veteran, due to a disability or for religious reasons, or as otherwise provided under applicable law.

Workday prohibits taking adverse action against any candidate or employee for reporting a possible violation of this policy, requesting one or more work accommodations, exercising a privacy right, or cooperating in an investigation in accordance with applicable law. Any employee who retaliates against a candidate or employee for doing so may be subject to disciplinary action, up to and including termination of employment, to the fullest extent allowable under applicable law.

If you require a reasonable accommodation, you may email [email protected], as far in advance as possible.

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