Job Description

The Aspen Group (TAG) is one of the largest and most trusted retail healthcare business support organizations in the U.S., supporting over 16,000 healthcare professionals and team members at more than 1,200 health and wellness offices across 46 states. TAG provides centralized business support services that power four consumer-facing brands: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, and Chapter Aesthetic Studio. Our team is united by a single purpose: to prove that healthcare can be better and smarter for everyone.

The Role

We are seeking a Senior Business Applications Engineer to own the day-to-day operations of our enterprise Workforce Management platform and a portfolio of business applications supporting 1,000+ locations across multiple brands.

This is a hands-on senior IC role. The person in this seat keeps the platform running reliably, builds/architects the integrations and automations that reduce manual overhead, and is the first call when something breaks. They know the system deeply enough to diagnose issues independently, drive vendor escalations with technical credibility, and translate operational needs into working solutions without waiting for someone else to define the approach.

Success here looks like a stable platform, including integrations, documented processes, and an educated team around them that can handle routine support work because this person took the time to build that coverage deliberately.

Essential Responsibilities

Platform Ownership & Technical Direction

• Set the technical direction and standards for the enterprise Workforce Management platform across 1,000+ locations — owning configuration architecture, access models, and the decisions that define how the platform scales as new locations and brands come online.
• Make the build, configure, and lifecycle calls — determine when to automate, when to re-architect, and when a system should be replaced or retired, and bring those recommendations forward with supporting analysis.
• Own intake and solution design end to end — translate operational and business needs into technical specifications and delivery plans, and serve as the accountable owner for delivery quality.

Systems Integration & Automation

• Design the integration architecture connecting the Workforce Management platform with HR, payroll, financial, and data warehouse systems — defining the data flows that other work depends on.
• Build and own automation that replaces manual recurring processes, reduces operational overhead, and improves data reliability across connected systems.
• Maintain the data pipelines that feed workforce analytics reporting, ensuring accuracy and security across the chain.

Operational Reliability & Incident Response

• Lead resolution of high-priority production incidents affecting workforce operations, and own restoration of service within defined response and resolution targets.
• Own platform health proactively through monitoring, alerting, maintenance, and performance optimization — identifying and resolving risk before it reaches the field.
• Direct vendor escalations and hold external partners accountable to resolution commitments on behalf of the organization.

Cross-Functional Coordination

• Serve as the senior technical liaison between field-facing operational impact and engineering or vendor resolution — coordinating across HR, Finance, Data, Workforce Strategy, Identity, and IT infrastructure teams.
• Provide the technical point of view in operational reviews and, alongside the team manager, in leadership forums where platform decisions and roadmap trade-offs are made.
• Manage vendor relationships and configuration alignment for the systems in scope, including defect management and product roadmap input.

Portfolio Support & Lifecycle

• Support a portfolio of connected business applications on enhancement projects, with the flexibility to take on additional applications as priorities shift.
• Lead migrations and decommissioning — own the transition plan and continuity when platforms are introduced, consolidated, or retired.
• Establish documentation and self-service — runbooks, SOPs, and reference material that reduce dependency on engineering for routine requests.

Mentorship & Knowledge Continuity

• Develop junior resources — distribute repeatable support work, review their output, and serve as their technical escalation point and guide.
• Eliminate single points of failure by transferring platform knowledge through documentation and structured mentorship, building sustainable coverage across the team.
• Contribute to sprint planning and capacity management for the work within this role's scope.

Requirements & Qualifications

• Bachelor's degree in Information Systems or a related field, or an equivalent combination of education and experience.
• 6+ years of progressive experience owning and supporting enterprise business applications, including demonstrated senior-level ownership of a workforce management or comparable operational platform at scale; multi-site, high-location-count environments strongly preferred.
• Demonstrated experience designing and maintaining system integrations across HR, payroll, and enterprise data platforms using APIs, middleware, or custom pipeline development.
• Proficiency in a scripting or automation language (Python or equivalent) for pipeline development and process automation.
• Strong working knowledge of SQL and data analysis; experience with cloud data warehouse environments a plus.
• Familiarity with HRIS, payroll, or ERP platforms; Workday experience preferred.
• Experience with production monitoring, alerting, and incident response.
• Proven ability to manage vendor relationships and hold external partners accountable to delivery and service commitments.
• Strong written and verbal communication; able to translate technical complexity for non-technical business stakeholders.
• Able to work independently, exercise sound technical judgment with minimal oversight, and guide work across remote, cross-functional teams.
• Highly self-motivated, detail-oriented, and able to prioritize effectively in a fast-moving environment.

*This role is onsite 4 days/week in our Chicago office (Fulton Market District)

• A generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match
• Salary: $125-147k