Full-Time

Workday Agile Delivery Lead

Posted on 2/21/2026

The Aspen Group

The Aspen Group

1,001-5,000 employees

Healthcare provider network enabling accessible care

Compensation Overview

$130k - $155k/yr

Chicago, IL, USA

In Person

Category
Engineering Management (1)
Required Skills
Workday HRIS
JIRA
SCRUM
Confluence
Requirements
  • 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.
  • 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
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
Desired Qualifications
  • Workday certification(s) in HCM, Payroll, or Financials is a plus.

TAG supports a nationwide network of dental and healthcare brands by providing the systems, training, and resources clinics need to run effectively and reach more patients. It operates a shared platform with Aspen Dental, Chapter, ClearChoice, WellNow, and AZPetVet, delivering brands, services, and operational support to streamline practice management and pricing transparency. Unlike firms that only sell equipment or marketing or run independent practices, TAG unites multiple care domains under one umbrella to empower providers with centralized resources. Its goal is to bring better, more accessible healthcare to more people by enabling clinicians and teams to deliver care where patients are across specialties.

Company Size

1,001-5,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Chicago, Illinois

Founded

N/A

Simplify Jobs

Simplify's Take

What believers are saying

  • Centralized commercial leadership can improve cross-brand patient acquisition and conversion.
  • AI diagnostic tools increased patient acceptance of recommended care by 12% across offices.
  • ClearChoice delivered over 50,000 3D-printed prostheses, validating scalable digital lab workflows.

What critics are saying

  • Masood's retail-first playbook clashes with healthcare economics, wasting spend within 12 months.
  • AI-enabled engagement failures directly reduce bookings, trust, and revenue across 1,400 locations.
  • Rapid implant scaling creates quality-control lapses, rework, and complaints within 24 months.

What makes The Aspen Group unique

  • TAG unifies Aspen Dental, ClearChoice, WellNow, Chapter, and Lovet under one platform.
  • Rafeh Masood, appointed May 14, 2026, leads brand, growth, and digital strategy.
  • TAG supports 1,400 locations across 48 states, serving over nine million annual patients.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Unlimited Paid Time Off

401(k) Company Match

Company News

PR Newswire
Mar 10th, 2026
TAG reports double-digit revenue growth across healthcare portfolio with $19M donated dental care

The Aspen Group, one of the largest healthcare support organisations in the US, has reported nearly double-digit revenue growth across its multi-brand platform spanning dental, urgent care, veterinary and aesthetics services. In 2025, TAG supported providers served more than nine million patients across 1,400 locations in 46 states. The company expanded implant training capacity by over 25% year-over-year, with several hundred doctors completing advanced surgery programmes. TAG-supported offices utilising AI diagnostic tools reported a 12% increase in patient acceptance of recommended care. ClearChoice delivered more than 50,000 3D-printed dental prostheses, whilst WellNow Urgent Care managed approximately 900,000 upper respiratory cases. Aspen Dental's network of independent practice owners grew by approximately 15% year-over-year. The funding supports continued expansion of implant capabilities and AI integration in 2026.

Dental Product Shopper
Oct 8th, 2025
The Aspen Group Earns Brandon Hall Group's "Best Use of AI for HR" Award

Phenom, an applied AI company that helps organizations hire faster, develop better and retain longer, announced The Aspen Group (TAG) earned the Brandon Hall Group(TM) Silver Award for Excellence in the 'Best Use of AI for HR' category.

PR Newswire
Jun 4th, 2025
The Aspen Group Breaks Down Barriers To Care By Introducing Smile Bridge ℠ In Partnership With The National Foundation For Ectodermal Dysplasias

Doctors from Aspen Dental and ClearChoice Dental Implant Centers join forces to provide transformative dental care solutions, free of charge, for patients impacted by ectodermal dysplasias.CHICAGO, June 4, 2025 /PRNewswire/ -- The Aspen Group (TAG), a leader in revolutionizing access to healthcare, is proud to announce a new partnership between the two dental brands it supports, Aspen Dental and ClearChoice Dental Implant Centers, and the National Foundation for Ectodermal Dysplasias (NFED). Together, they are launching Smile Bridge by The Aspen Group ℠, a groundbreaking program designed to connect patients with ectodermal dysplasia to the dental care they need, at no cost. This program will provide a lifetime of confident, healthy smiles for individuals impacted by this condition.Turning Inspiration into ImpactSmile Bridge was inspired by the work of Aspen Dental practice owner Dr. Whitney Deitz and lab technician Julie Bostwick, who created a set of dentures for Weston, a young patient with ectodermal dysplasia. Weston went on to earn a place in the Guinness Book of World Records as the youngest person to receive dentures. Ectodermal dysplasias are a group of inherited disorders that can cause defects in the hair, nails, sweat glands, and teeth

PR Newswire
Apr 29th, 2025
Aspen Dental Practice Owner Dr. Mithila Sharma Steps Into Clinical Support Leadership Role

CHICAGO, April 29, 2025 /PRNewswire/ -- Aspen Dental® today announced that Dr. Mithila Sharma, DDS, a successful Aspen Dental practice owner, has been appointed Director of Clinical and Prosthodontic Support. Dr. Sharma first joined Aspen Dental in 2013 as a lead dentist in Danville, Illinois, and quickly focused her career growth within Aspen Dental's practice ownership program, eventually becoming a multi-practice owner. Over the years, she has provided high-quality care to thousands of patients across the Chicagoland area and mentored dozens of clinical and support staff.Dr. Sharma's impact goes beyond patient care — she has played a key role in piloting innovative technologies in her offices, including 3D printing and digital implant systems

PR Newswire
Apr 18th, 2025
Lovet Pet Health Care Launches In Michigan To Expand Access As New Survey Reveals Cost Barriers For Pet Parents

New Survey: Nearly Half (44%1) of Michigan Pet Parents Surveyed Skipped or Delayed Vet Visits in the Past Year Due to Rising Veterinary CostsLovet Opens First Grand Rapids Hospital with Ribbon Chewing Ceremony Led by Four-Legged PatientGRAND RAPIDS, Mich., April 18, 2025 /PRNewswire/ -- Lovet Pet Health Care℠, a new kind of veterinary care that makes it easier—for both pets and their people—to access the support they need to stay healthy and happy, is expanding into Michigan with the opening of its 25th location nationwide—and first hospital in Grand Rapids—today. As part of its mission to make expert veterinary care more accessible, Lovet enters the market with its signature offerings—starting with a first exam free for all new clients, cost-saving care packages, same-day appointments for urgent care needs, and flexible payment options through Lovet Pay

INACTIVE