SR. Workday Manager, Application Development

Pinnacle99 Inc.; Chicago (IL); On-site; USD 140,000 - 180,000; Part time

Job summary

Pinnacle99 Inc. in Chicago, IL seeks a Sr. Manager, Application Development – Workday to lead the HR and Finance technology landscape.

This senior role guides technical teams and partners with senior business and IT leadership, balancing strategic direction with practical delivery. The ideal candidate has deep Workday experience across HCM/HR and Financials, plus strong foundations in application development.

Qualifications

• 8–10+ years of deep Workday experience
• Strong experience across Workday HCM/HR and Workday Financials
• Experience with Java and/or broader application development environments
• Strong leadership and people-management experience

Responsibilities

• Provide strategic and technical leadership for Workday applications supporting HR and Finance
• Lead application development, enhancement, integration, and support initiatives across the Workday ecosystem
• Partner with HR, Finance, IT, and senior executive stakeholders to establish priorities
• Provide technical direction and challenge architecture, design, and implementation decisions
• Lead and mentor application development and Workday technology teams
• Establish delivery priorities, monitor progress, and drive issues to resolution
• Communicate project status, risks, and dependencies to senior leadership
• Ensure Workday solutions align with business objectives and security requirements

Skills

Workday expertise

Technical leadership

Stakeholder management

Team leadership

Java / app dev

Cloud (AWS)

Tools

Java

AWS

Job description

Sr. Manager, Application Development – Workday

Location: Chicago, IL

Employment Type: Contract-to-Hire

Duration: 1+ Year

Job Overview

We are seeking a Sr. Manager, Application Development – Workday to lead application development and technology initiatives across the HR and Finance technology landscape.

The ideal candidate will bring deep Workday experience across both HCM/HR and Financials, combined with strong application development and technical leadership experience. This is a senior leadership role that requires someone who can guide technical teams, challenge technical decisions, manage delivery, and partner directly with senior business and IT leadership.

This role is not intended to be a day-to-day hands-on development position; however, the successful candidate must have a strong technical foundation and significant hands-on Workday experience earlier in their career.

Key Responsibilities

• Provide strategic and technical leadership for Workday applications supporting HR and Finance.
• Lead application development, enhancement, integration, and support initiatives across the Workday ecosystem.
• Partner with HR, Finance, IT, and senior executive stakeholders to establish priorities and deliver technology solutions.
• Provide technical direction and challenge architecture, design, and implementation decisions when necessary.
• Lead and mentor application development and Workday technology teams.
• Manage managers, employees, contractors, and external consultants.
• Establish delivery priorities, monitor progress, identify risks, and drive issues through resolution.
• Communicate project status, technical risks, dependencies, and delivery concerns to senior leadership.
• Ensure Workday solutions align with business objectives, technical standards, security requirements, and enterprise architecture.
• Drive continuous improvement across Workday applications, integrations, processes, and support models.
• Balance competing priorities and requirements across both HR and Finance organizations.
• Collaborate with vendors and implementation partners to ensure successful delivery.
• Provide leadership during production issues, escalations, enhancements, and major platform changes.

Required Qualifications

• 8–10+ years of deep Workday experience preferred; candidates with 6–8 years may be considered based on depth of experience.
• Strong experience across Workday HCM/HR and Workday Financials.
• Broad understanding of the Workday ecosystem, rather than experience limited to a single module.
• Experience with areas such as:
• Workday HCM
• Payroll
• Time Tracking
• Compensation
• Integrations
• Reporting and related Workday capabilities
• Experience with Java and/or broader application development environments.
• Strong leadership and people-management experience.
• Experience managing technical teams and preferably other managers.
• Experience leading teams consisting of employees, contractors, and consultants.
• Strong communication and executive stakeholder-management skills.

Preferred Qualifications

• Workday consulting experience with broad exposure across the Workday platform.
• Experience leading enterprise Workday implementations as well as post-production enhancements and support.
• Experience with Workday integrations and application architecture.
• Experience working directly with HR and Finance business leaders.
• Experience presenting technology roadmaps, delivery updates, risks, and issues to CIO-level or senior executive leadership.
• Strong understanding of enterprise application development and cloud technologies.

Ideal Candidate

The ideal candidate is a senior Workday technology leader who combines deep Workday HCM and Financials expertise with strong technical and application-development knowledge.

You should be comfortable moving between technical discussions, business requirements, team leadership, and executive-level conversations. The successful candidate will be someone who can drive accountability, make decisions, challenge appropriately, and take ownership of critical deliverables.

This position is not intended for candidates whose experience is limited to Workday administration, a single Workday module, or participation in only one Workday implementation. Broad Workday expertise across both HR and Finance, technical credibility, AWS exposure, and senior leadership experience are key to success in this role.