Learning Operations Specialist

Learning Operations Specialist — Contractor

United States

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

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.

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 ensure 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 Sana Insights that enable ongoing monitoring of program performance and eliminate the need for manual report pulls
• Create dashboards that surface results for the team in real time when surveys are launched in Sana
• Collect and consolidate training data from third-party courseware providers and incorporate into Sana reporting as needed
• Manage relationships with third-party courseware vendors, including contract tracking and content library maintenance

Program Operations & Logistics

• Support program logistics including enrollment, scheduling, and coordination for learning programs across the employee lifecycle
• Support phased rollouts of Sana and Udemy, including launch preparation, post-launch troubleshooting, learner communication, and recommending iterative improvements between phases based on feedback and usage data
• Manage the TD communications and production calendar and coordinate launch support for new programs, courses, and initiatives
• Create and maintain process documentation, SOPs, and playbooks so team knowledge is not dependent on any one person
• Support the creation of QA checklists and content standards for decentralized content creators across the organization

Learner Support & Team Collaboration

• Respond to LMS support inquiries submitted through agreed-upon channels within agreed-upon response timeframes
• Respond to support inquiries with a friendly, responsive, and solutions-oriented approach
• Surface patterns from learner support inquiries and recommend process or content improvements to reduce recurring issues
• Collaborate with internal teams as needed, including IT, People Tech, and team leads, and the broader Talent Development team
• Contribute to admin, execution, and launch work as part of a small team where everyone pitches in
• Adapt hours and availability around program launches and key milestones

Desired Skills & Experience

• Previous experience delivering projects or managing operations within Learning and Development, Talent Development, or People Operations functions
• Demonstrated ability to manage multiple concurrent workstreams and deliver against defined project timelines
• Proven experience implementing, administering, or managing a Learning Management System (LMS)
• Experience troubleshooting LMS workflows, automations, and integrations
• Demonstrated experience applying AI tools (e.g., ChatGPT, Claude, Gemini) to accelerate delivery of operational work including communications, documentation, and data analysis
• Demonstrated ability to identify issues and surface recommendations proactively as part of project delivery
• Strong experience with reporting and data analysis within LMS platforms
• Demonstrated ability to manage client communication and inquiry management on project engagements, including timely and solutions-oriented responses to support requests
• Experience creating and maintaining process documentation and SOPs
• Ability to deliver independently against a defined scope of work

Bonus Points

• Experience with Sana LMS
• Experience working with HRIS integrations such as Workday
• Experience managing third-party courseware integrations and vendor relationships
• Experience supporting program logistics, enrollment operations, or learning program launches
• Experience defining launch metrics and building reporting dashboards or data visualizations within LMS platforms, with the ability to work in other tools as needed