Learning Operations Specialist — Contractor

Hours: Up to 35 hours a week Duration: 6 months Schedule: Availability expectations will be mutually agreed upon at engagement start and will generally align with standard business hours Monday through Friday. Additional availability may be requested around program launches and key milestones, subject to mutual agreement between the Company and the contractor. Compensation: $53.50/hour About Us At SimplePractice, we are improving access to quality care by equipping health and wellness clinicians with all the tools they need to thrive in private practice. More than 250,000 providers trust SimplePractice to build their business through our industry-leading software with powerful tools that simplify every part of practice management. From admin work to clinical care, our suite of innovative solutions work together to reduce administrative burden—empowering solo and small group practitioners to thrive alongside their clients. Award-winning and people-first, SimplePractice is shaping the future of health tech. Recognized by MedTech Breakthrough, the Digital Health Awards, and BuiltIn's Best Places to Work. The Role SimplePractice is seeking an independent contractor with demonstrated expertise in learning operations and LMS administration to support a six-month project engagement with our Talent Development function. This engagement is central to the buildout of our learning ecosystem from the ground up, and will require a contractor who can deliver specialized services across LMS administration, HRIS and courseware integrations, program logistics, reporting, vendor management, and process documentation. The contractor will bring deep technical proficiency in LMS platforms, a proven ability to build systems and surface data-driven recommendations, and a client-focused approach to inquiry management and issue resolution. Experience applying AI tools to accelerate delivery — including drafting communications, building documentation, and identifying patterns in learner data — is strongly preferred. We are currently launching Sana and Udemy in phases. These platforms are new to the organization, and the rollout will require ongoing configuration, support, troubleshooting, and iterative improvements as we learn what works. The contractor will provide specialized services to ensure each phase launches smoothly and that the systems are refined and optimized based on defined project outcomes. This is an engagement estimated at up to 35 hours per week, though the nature of the work will vary across the engagement period. Some services are ongoing throughout the engagement (LMS administration, learner support), some are cyclical around program launches (communications, enrollment, dashboard creation), and some are foundational deliverables that taper once systems and processes are established (documentation, SOPs, QA checklists). Priorities and active workstreams will be determined through regular project check-ins and mutual agreement between the Company and the contractor. SimplePractice operates in a Slack-based environment and Slack is the primary communication channel across the organization. The contractor will receive and respond to project communications and support inquiries primarily through Slack, with response expectations and protocols to be agreed upon at engagement start.. Scope of Services LMS Administration & Systems Administration and maintenance of Sana LMS, including course configuration, learner access, group management, and content publishing Monitor and validate learner data feeds from Workday to ensure accurate synchronization within Sana Configure and maintain automations that support onboarding workflows and training assignments Troubleshoot LMS issues and including training assignments, automations, and integrations are functioning properly Define and recommend key metrics for new course and program launches in Sana, proposing what to track and why based on program goals Build and maintain reporting dashboards in…