Workday Agile Delivery Lead

The Aspen Group (TAG) is one of the largest and most trusted retail healthcare business support organizations in the U.S. and has supported over 16,000 healthcare professionals and team members at more than 1,200 health and wellness offices across 46 states in three distinct categories: Dental care, urgent care, and medical aesthetics. Working in partnership with independent practice owners and clinicians, the team is united by a single purpose: to prove that healthcare can be better and smarter for everyone. TAG provides a comprehensive suite of centralized business support services that power the impact of four consumer-facing businesses: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio and our newest addition Lovet. Each brand has access to a deep community of experts, tools and resources to grow their practices, and an unwavering commitment to delivering high-quality consumer healthcare experiences at scale.

Our continued growth has created an opportunity to join our IT Team as a Workday Agile Delivery Lead. We are looking for an experienced Workday Agile SCRUM/Scaled Agile Delivery Lead with a strong SCRUM background. This candidate will oversee and manage the Agile delivery process of our Workday projects to deliver Workday features and functions across our organization. The ideal candidate will be responsible for coordinating across teams, managing delivery timelines, and ensuring alignment with Agile and/or Scaled Agile (SAFe) practices. This role requires an understanding of Workday functional areas – HCM and FINS, as well as expertise in agile principles, especially in a scaled environment to drive collaboration, productivity, and accountability.

Essential Responsibilities

• Lead Agile Practices: Facilitate SCRUM ceremonies (daily stand-ups, sprint planning, sprint reviews, retrospectives) to keep the Workday team focused, aligned, and working efficiently within Agile principles. Facilitate Agile ceremonies, including sprint planning, daily stand-ups, sprint reviews, and retrospectives.
• Scaled Agile Implementation: Drive SAFe transformation across the teams by implementing and standardizing scaled agile practices. Coordinate with other Agile Release Trains (ARTs) and SCRUM teams to ensure alignment on program objectives and dependencies. Lead Program Increment (PI) planning sessions, including preparation, facilitation, and follow-up activities. Drive adherence to Scaled Agile (SAFe) principles and processes, ensuring seamless cross-team coordination.
• Manage Workday Delivery Lifecycle: Oversee and coordinate end-to-end Workday features and functions delivery from requirements gathering to deployment, ensuring timely and quality completion of project goals. Collaborate closely with product owners, developers, testers, and other stakeholders to align Workday configurations with business needs. Collaborate closely with product owners, developers, testers, and other stakeholders to align Workday configurations with business needs. Monitor and manage delivery schedules, resource allocation, and key project milestones to meet scope, timeline, and budget objectives. Identify, manage, and mitigate risks to delivery, escalating issues as needed.
• Stakeholder Collaboration and Engagement: Work closely with stakeholders, including business users, Workday product owners, developers, and IT managers, to prioritize and align requirements, address project dependencies, and set realistic expectations. Act as a liaison between technical teams, product owners, and business stakeholders to align on requirements, delivery timelines, and expectations. Provide regular updates and reporting on project status, progress, and metrics to senior leadership and stakeholders. Foster a culture of continuous improvement, ensuring that stakeholder feedback is captured, reviewed, and incorporated into future planning.
• Drive Continuous Improvement: Analyze and improve delivery processes through metrics and feedback, implementing best practices to enhance team performance, velocity, and delivery speed.
• Risk and Issue Management: Identify potential risks and obstacles early, proposing and implementing mitigation strategies to keep projects on track.
• Team Development, Empowerment and Leadership: Coach, mentor, and empower team members to improve productivity and ownership, fostering a culture of collaboration, transparency, and accountability. Mentor and develop SCRUM Masters, product owners, and other team members in Agile and SAFe practices. Provide training on agile methodologies and promote a collaborative team environment.
• Reporting and Tracking: Use tools (e.g., JIRA, Workday reporting) to track project progress and maintain visibility into the project lifecycle, providing timely updates to stakeholders.
• Agile Mindset: Promote Agile and Lean principles within the organization, encouraging experimentation, adaptation, and learning.
• Resource Allocation: Assist in team capacity planning, ensuring proper resource allocation and skill alignment for project needs.
• Workday System Expertise: Maintain up-to-date knowledge of Workday capabilities, updates, and best practices, ensuring alignment between technical solutions and business goals.
• Meet Expectations: Meet/exceed the customer’s (internal and external) expectations by understanding, anticipating, and meeting customer needs. Exhibit proactive communication; act and think with customers in mind. Friendly, enthusiastic, and energetic with customers, co-workers, managers, and visitors. Promote and project a positive company image; treats others with courtesy and respect

Requirements/Qualifications

• Bachelor’s degree in information systems, or equivalent combination of education & experience is required with an emphasis in Information Systems, or related field strongly preferred.
• 5 years of experience as a SCRUM Master, Agile Delivery Lead, or in a similar role in the Workday ecosystem delivery required.
• Proficiency in SAFe, Scrum, Kanban, and other Agile methodologies required.
• Certified SAFe Agilist or SAFe Program Consultant (SPC) is required
• Certified SCRUM Master (CSM) or equivalent Agile certification required
• 5 years of experience leading Agile/SCRUM teams, with 2 years specifically managing Workday deliverables required.
• Strong knowledge of Workday implementation, configurations, and delivery best practices required.
• Proficient in Agile tools (e.g., JIRA, Confluence) and Workday-specific project tracking tools.
• Expertise in Workday HCM, Payroll, Financials, or other Workday modules required
• Proven experience in leading scaled agile frameworks (preferably SAFe) required
• Extensive knowledge of Agile tools (e.g., Jira, Rally) and Workday project management tools.
• Familiarity with Workday’s architecture and configuration best practices is preferred.
• Workday certification(s) in HCM, Payroll, or Financials is a plus.
• Strong analytical skills, problem solving and troubleshooting abilities
• Ability to work independently as well as in a team environment, especially with remote teams
• Strong written and verbal communication skills
• Highly self-motivated, self-directed, and attentive to detail
• Ability to effectively prioritize and execute tasks in a high-pressure environment
• Extensive experience working in a team-oriented, collaborative environment

• This role is onsite 4 days/week in our Fulton Market office in Chicago
• Annual pay range: $130,000-153,000 /year
• A generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match