Remote Payroll Director Jobs (NOW HIRING)

Job Description: CSMC is seeking a dynamic, strategic, and forward-thinking Payroll Director to lead, scale, and optimize our payroll operations across all supported client schools for one of our affiliate companies. In this critical leadership role, you will own the design and execution of a high-performing payroll function—managing operational structures, workflows, team development, and cutting-edge system automation (including AI and advanced system utilization). As the ultimate escalation point for complex payroll matters, you will ensure seamless client school onboarding/offboarding, reduce organizational risk, and champion a culture of continuous improvement. Beyond daily operations, you will serve as a strategic partner to executive leadership and act as an external brand ambassador and subject matter expert (SME) at industry conferences and forums. Position Summary CSMC Payroll Director is responsible for the overall leadership, strategy, and performance of payroll operations across all supported schools. This role oversees Payroll Managers and the broader payroll team, ensuring services are delivered with accuracy, compliance, consistency, and scalability. The Payroll Director owns the design and execution of a high-performing payroll function, including operational structure, systems, workflows, and team development. This role is also responsible for ensuring seamless onboarding and offboarding of client schools, maintaining a high-quality client experience, and aligning payroll operations with organizational growth. The Payroll Director serves as the ultimate escalation point for complex payroll matters, while focusing on building systems and processes that reduce risk, improve efficiency, and support long-term scalability. In addition to operational leadership, the Payroll Director serves as a strategic partner to executive leadership and an external representative of company, contributing to thought leadership, professional development, and industry engagement. Essential Functions: Strategic Leadership & Department OversightLead and oversee all payroll operations across the organizationDefine and execute the strategic vision for payroll servicesEnsure payroll operations are structured to support organizational growth and multi-state scalabilityEstablish departmental goals, priorities, and performance expectationsBuild and maintain a high-performing payroll leadership team Organizational Design & Team LeadershipMaintain advanced operational mastery of all payroll leadership functions within the department, including payroll operations, quality control, training, payroll tax support, retirement reporting, compliance workflows, reconciliations, audit readiness, and payroll systems administrationServe as the department’s highest-level subject matter expert across all payroll operational and compliance functionsProvide direct guidance, coaching, troubleshooting, and operational leadership support to Payroll Managers as neededMaintain the ability to independently execute, review, troubleshoot, and oversee all core functions performed by Payroll Managers and Payroll SpecialistsEnsure operational continuity by stepping into leadership or operational coverage roles during vacancies, transitions, escalations, staffing shortages, or other business continuity eventsLead development of managerial expertise and ensure leadership team members maintain proficiency across all critical payroll functions and systems. Oversee Payroll Manager and Payroll & Retirement Manager roles and overall team structureEnsure clear role definition, ownership, and accountability across all payroll functionsOversee hiring, onboarding, and long-term workforce planning for the payroll departmentFoster a culture of accountability, collaboration, and continuous improvement Departmental Mastery & Operational CoverageMaintain expert-level working knowledge of all payroll workflows, controls, reporting requirements, and operational processes managed within the departmentMaintain operational proficiency across all supported payroll systems, including but not limited to Ascender, Skyward, WebSmart, and related reporting platformsMaintain deep understanding of:Payroll processing operationsPayroll quality control frameworksPayroll tax operational workflowsIRS reporting and quarterly filing processesW-2 processing and year-end balancingState Retirement reporting and reconciliationsAudit readiness and compliance proceduresPayroll onboarding and implementation processesProvide strategic and operational guidance to Payroll Managers regarding complex payroll issues, workflow design, compliance concerns, reconciliations, and process improvementsEnsure department leadership maintains cross-training and operational redundancy across all major payroll functionsMaintain readiness to directly support or temporarily assume operational responsibilities when needed to ensure uninterrupted payroll services and compliance Payroll Operations & Service Delivery OversightEnsure payroll services are delivered accurately, timely, and consistently across all schoolsMonitor operational performance, workloads, and service delivery standardsEnsure alignment across payroll functions, including:Payroll processingQuality controlTRS and compliance reportingProvide guidance and oversight on complex or high-risk payroll matters Innovation, Automation & Operational StrategyEstablish and lead the strategic direction for automation, AI utilization, and system optimization within payroll operationsIdentify and implement scalable solutions that reduce manual effort and improve operational efficiencyEvaluate and introduce new technologies, tools, and integrations to support organizational growthEnsure alignment of automation and process improvements with overall business strategyPromote a culture of innovation, continuous improvement, and forward-thinking across the payroll function Client Onboarding & Offboarding Own and oversee the onboarding of all new client schools, ensuring a seamless transition into payroll servicesDesign and maintain a standardized onboarding process, including:Data collection and validationSystem setup and configurationPayroll calendar alignmentCommunication and training with school teamsEnsure successful parallel payroll runs and go-live readinessOversee offboarding processes to ensure:Accurate final payroll processingProper documentation and data transitionCompliance with all reporting and close-out requirementsContinuously improve onboarding/offboarding processes for efficiency and client experience Process Design, Standardization & ScalabilityEnsure all payroll processes are documented, standardized, and scalableOversee development and maintenance of SOPs across all payroll functionsIdentify opportunities for efficiency, automation, and system optimizationPartner with leadership to implement new tools, systems, and integrationsEnsure a single source of truth for payroll data, workflows, and documentation Risk Management & Compliance OversightEnsure compliance with all Federal, State, and agency payroll requirementsOversee TRS reporting accuracy and compliance in partnership with Payroll & Retirement ManagerMonitor risk areas and implement controls to mitigate exposureServe as escalation point for high-risk payroll issues and compliance concernsEnsure audit readiness and support internal and external audits Financial & Data Integrity OversightEnsure accuracy and integrity of payroll data and reportingPartner with Finance on:Payroll reconciliationsCash flow considerationsFinancial reporting alignmentOversee tax filings, TRS reporting, and year-end processes at a high level Client Experience & Relationship ManagementEnsure high-quality payroll service delivery across all schoolsMonitor client satisfaction and address systemic service issuesSupport client retention and growth through strong service deliveryPartner with executive leadership on client relationships as needed Executive Partnership & Organizational LeadershipRegularly consult with executive leadership on payroll operations, risks, and strategic initiativesProvide insight and recommendations related to payroll trends, compliance, and organizational impactSupport executive decision-making through data analysis and operational expertiseContribute to cross-functional strategic planning and organizational initiatives Industry Representation & Thought LeadershipRepresent company at conferences, professional events, and industry forumsAttend conferences for professional development and to stay current on payroll trends and regulationsPresent at conferences as a payroll subject matter expert (SME) when applicableDevelop and deliver webinars and training sessions for clients and external audiencesContribute to building company reputation as a leader in payroll services for schools Cross-Functional & Organizational CollaborationCollaborate with HR, Finance, and leadership on organizational initiativesEnsure alignment between payroll operations and other service areasSupport integration of payroll services within broader organizational strategy Systems & InnovationOversee payroll system strategy and optimization across platforms (Ascender, Skyward, Websmart, etc.)Ensure effective use of systems to support automation, accuracy, and scalabilityEvaluate and implement new technologies to improve payroll operationsEnsure data governance and system integrity Additional ResponsibilitiesPerform other duties as assigned to support departmental and organizational needs Education and Experience: Education: Bachelor’s degree in Accounting, Finance, Business, or related field (or equivalent)Experience: Minimum 7 years of related experience in a related role, two of which must be in a school or school support setting in a leadership roleExperience leading teams and scaling payroll operations in a multi-entity environmentDemonstrated mastery of payroll operations, payroll compliance, retirement reporting, payroll quality control, payroll tax processes, workflow design, training development, and operational leadershipExtensive experience leading and mentoring payroll managers and developing operational leadership capacityAdvanced working knowledge of payroll tax processes, including quarterly filings, reconciliations, year-end reporting, and payroll operational controlsAdvanced knowledge of retirement reporting processes, reconciliations, corrections, and compliance requirements in school-based payroll environmentsDemonstrated ability to independently troubleshoot and resolve complex payroll operational and compliance issues across multiple systems and clientsPreferred:Related experience in a remote environment.Related Certification. Knowledge, Skills, and Abilities: · Communication Skills: Ability to communicate clearly, professionally, and effectively in both written and verbal formats. · Relationship Management: Ability to build and maintain positive working relationships with colleagues, leadership, vendors, and school clients. · Attention to Detail: Strong accuracy in data entry, documentation, and compliance-related tasks. · Time and Task Management: Ability to prioritize tasks, manage multiple deadlines, and work efficiently in a fast-paced environment. · Independent Work: Ability to perform routine responsibilities with minimal supervision while exercising sound judgment. · Customer Service Orientation: Demonstrates a responsive, solutions-oriented approach when supporting schools and employees. · Analytical and Problem-Solving Skills: Ability to identify issues, analyze information, and recommend appropriate solutions. · Clerical and Technical Skills: Proficient in general administrative functions, including data entry, document management, and HR/Payroll systems. · Mathematical Skills: Ability to perform basic calculations accurately (e.g., benefits reconciliation, payroll-related support). · Adaptability: Ability to remain flexible and composed under pressure while managing competing priorities. · Keyboarding Skills: Minimum typing speed of 35 words per minute. · Advanced operational knowledge of all payroll management functions performed within the department · Ability to train, mentor, coach, and develop Payroll Managers and operational leadership staff · Ability to independently review, audit, troubleshoot, and resolve complex payroll operational and compliance matters · Ability to provide hands-on operational support and leadership coverage when necessary · Strong understanding of payroll systems architecture, integrations, operational workflows, and reporting dependencies · Strong knowledge of payroll operational controls, quality assurance processes, audit preparation, and risk mitigation strategies Supervisory Responsibilities: · Payroll Managers - all specialties · Indirect oversight of Payroll Specialists (Levels I–III) Core Values: As a valued member of our team, you will be expected to uphold and embody our company’s core values of: · Integrity · Accountability · Diversity · Passion · Leadership · Collaboration, and · Quality These values serve as the foundation of our organization and guide our interactions with colleagues, schools, and vendors. Your commitment to these principles will contribute to a positive and productive work environment. Physical Demands: Must possess mobility to work in a standard office setting and use standard office equipment, including a computer; vision to read printed materials and a computer screen; and hearing and speech to communicate in person and over the telephone. This is primarily a sedentary office classification although standing and walking between work areas may be required. Finger dexterity is needed to access, enter, and retrieve data using a computer keyboard or calculator and to operate standard office equipment. Positions in this classification occasionally bend, stoop, kneel, reach, push, and pull drawers open and closed to retrieve and file information. Employees must possess the ability to lift, carry, push, and pull materials and objects weighing up to 15 pounds. Environment: As a remote employee, you will have the flexibility to work from the comfort of your own home. This allows for a more personalized and efficient work environment. You will need to have a dedicated workspace with reliable internet access and the necessary equipment to perform your job duties. While working remotely offers many benefits, it also requires strong self-discipline, effective time management, and excellent communication skills to maintain productivity and collaborate effectively with team members. Travel: While infrequent, travel may be required to conferences, meetings, and professional development training as needed. Company Description: At CSMC, we