Sr. Business Applications Specialist - HR (Contractor)

Chicago Cubs•Chicago, IL

20h•Hybrid

About The Position

We are seeking a Senior Business Applications Specialist to oversee, support, and enhance the enterprise applications ecosystem within the HR department. This role will primarily oversee the Workday HRIS system, in addition to other HR technology platforms that power HR operational excellence. The ideal candidate is a hands-on problem solver who thrives in a dynamic, fast-moving environment and enjoys collaborating with internal teams to optimize systems and streamline business processes. A core focus for this person will be on strategic work efforts that begin with an understanding of the current state, determining a future state roadmap that aligns to key business processes driven and identified by current HR leadership, and focusing on the implementation of these changes within Workday and impacted systems. Additionally, the person best suited for this role is able to thrive as an HRIS team of one with the ability to teach HR colleagues how to become advanced users of tools and technologies. This hybrid position is based in the city of Chicago and requires three days onsite each week.

Requirements

7+ years of experience managing and supporting enterprise applications in a fast-paced, cross-functional environment.
4+ years of hands-on experience managing Workday.
Strong understanding of HR workflows, processes, and data governance.
Proven ability to balance operational support with strategic improvements.
Excellent communication and problem-solving skills with a collaborative, customer-focused mindset.
Must be able to work onsite three days per week at the Chicago office.

Responsibilities

Configure and maintain enterprise applications to meet evolving business requirements.
Partner with functional leads and vendors to deliver tailored configurations and integrations.
Oversee system settings, workflows, and permissions to maintain data integrity and usability.
Support enhancements within Workday modules —particularly time tracking, absence, payroll, and HCM—ensuring efficiency and accuracy to align with business needs.
Evaluate existing processes to identify automation opportunities and technology-based improvements.
Stay current on platform capabilities, participating in version updates, release testing, and projects.
Contribute to change management and communication efforts, ensuring smooth adoption of new functionality.
Coordinate with internal teams and external partners during system upgrades and enhancement cycles.
Create efficiency in supporting the HRIS and other HR Technologies through the creation of SOPs, user guides and hands-on training with members of the HR team.
Provide tier-2 application support for internal users, escalating issues to vendors or specialized teams as necessary.
Analyze and resolve user issues related to access, configuration, data flow.
Partner with IT to support setup and maintenance of integrations.
Document recurring problems and propose long-term solutions that improve platform reliability and efficiency.
Collaborate with business stakeholders to ensure optimal system performance and usability across departments.
Develop and maintain reporting for Business leaders, HR colleagues and other internal partners.
Understand business needs to create and adapt reports or dashboards containing relevant KPI information.
Look for gaps in data integrity and provide solutions to ensure accuracy.