Sr Associate IS Bus Sys Analyst – Workday Benefits

Milestone Technologies is a global IT managed services firm that partners with organizations to scale their technology, infrastructure and services to drive specific business outcomes such as digital transformation, innovation, and operational agility. Milestone is focused on building an employee-first, performance-based culture and for over 25 years, we have a demonstrated history of supporting category-defining enterprise clients that are growing ahead of the market. The company specializes in providing solutions across Application Services and Consulting, Digital Product Engineering, Digital Workplace Services, Private Cloud Services, AI/Automation, and ServiceNow. Milestone culture is built to provide a collaborative, inclusive environment that supports employees and empowers them to reach their full potential.

Our seasoned professionals deliver services based on Milestone's best practices and service delivery framework. By leveraging our vast knowledge base to execute initiatives, we deliver both short-term and long-term value to our clients and apply continuous service improvement to deliver transformational benefits to IT. With Intelligent Automation, Milestone helps businesses further accelerate their IT transformation. The result is a sharper focus on business objectives and a dramatic improvement in employee productivity. Through our key technology partnerships and our people-first approach, Milestone continues to deliver industry-leading innovation to our clients. With more than 3,000 employees serving over 200 companies worldwide, we are following our mission of revolutionizing the way IT is deployed.

Sr Associate IS Bus Sys Analyst – Workday Benefits

Roles & Responsibilities:

• Collaborate with Product Managers and System Architects to manage Workday Benefits configuration and analysis activities aligned with business objectives.
• Gather and translate business needs into Workday Benefits configuration requirements, ensuring compliance and accuracy.
• Configure and maintain benefit plans, eligibility rules, benefit groups, enrollment events, and dependent verification logic.
• Lead the setup and execution of Open Enrollment, Life Event processing, and Benefit Event auditing.
• Partner with business stakeholders to define scope and value of new benefits configurations or enhancements.
• Manage backlog items, ensuring benefit configuration deliverables are prioritized and tested effectively.
• Define clear Acceptance Criteria and Definition of Done for all Benefits-related configuration changes.
• Work with UX and HR Operations to streamline employee enrollment experience and process flow.
• Validate and troubleshoot benefit event processing, eligibility intersections, and enrollment discrepancies.
• Conduct configuration demonstrations and training sessions for HR teams and end users.
• Maintain up-to-date documentation of benefit configurations, workflows, and eligibility logic for audit and support purposes.

Required Skills & Experience

• Min 7+ years of hands-on Workday configuration experience with strong expertise in Benefits Administration.
• Proven ability to configure and manage core, optional, and flex benefit plans, including eligibility and coverage rules.
• In-depth understanding of event processing, open enrollment setup, and dependent verification configuration.
• Strong analytical and problem-solving skills with the ability to translate complex benefits policies into system logic.
• Experience with end-to-end Workday implementations or major enhancements.
• Excellent documentation, communication, and stakeholder engagement skills.
• Workday Benefits certification preferred.
• Exposure to Agile delivery practices and global HR operations.

Preferred Qualifications

• Experience with multi-country benefits configuration and local compliance alignment.
• Familiarity with integrations between Workday Benefits, Payroll, and HCM modules.
• Understanding of benefit provider file feeds and event-based automation.

Professional Certifications:

• • SAFe for Teams certification (preferred)

Soft Skills:

• • Able to work under minimal supervision
• Excellent analytical and gap/fit assessment skills
• Strong verbal and written communication skills
• Ability to work effectively with global, virtual teams
• High degree of initiative and self-motivation
• Ability to manage multiple priorities successfully
• Team-oriented, with a focus on achieving team goals
• Strong presentation and public speaking skills

Estimated Pay Range:

Exact compensation and offers of employment are dependent on circumstances of each case and will be determined based on job-related knowledge, skills, experience, licenses or certifications, and location.

At Milestone we strive to create a workplace that reflects the communities we serve and work with, where we all feel empowered to bring our full, authentic selves to work. We know creating a diverse and inclusive culture that champions equity and belonging is not only the right thing to do for our employees but is also critical to our continued success.

Milestone Technologies provides equal employment opportunity for all applicants and employees. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race, color, religion, gender, gender identity, marital status, age, disability, veteran status, sexual orientation, national origin, or any other category protected by applicable federal and state law, or local ordinance. Milestone also makes reasonable accommodations for disabled applicants and employees.

We welcome the unique background, culture, experiences, knowledge, innovation, self-expression and perspectives you can bring to our global community. Our recruitment team is looking forward to meeting you.