Payroll and Benefits Specialist

Job Details Role Type: Full-Time Location: Fully remote (based anywhere in the United States) Reports to : Financial Accountant About this role Parallel is seeking a full-time Payroll and Benefits Specialist. In this role, you’ll support the Finance and People Teams by owning the operational aspects of payroll and benefits administration, compliance, and employee support. This is not a plug-and-play role. We are a fast-growing startup where systems are still being built, processes are evolving, and historical inconsistencies exist that need to be resolved. You will play a key role not only in running day-to-day payroll and benefits operations, but also in helping build, standardize, and improve them over time. This is a great opportunity for someone who wants to: Make an impact: You are motivated by a mission-driven culture and want your work to directly support employees and operations Join a fast-growing startup: You enjoy solving ambiguous problems and building structure where it doesn’t yet exist Act as a bridge between Finance and HR: You’re comfortable collaborating cross-functionally and navigating different priorities Take ownership: You thrive in ambiguity, are comfortable fixing while operating, and proactively identify and resolve issues Build for scale: You want to create processes that are efficient, sustainable, and scalable as the company grows Be part of a collaborative culture: You want to work hands-on with your team and cross-functional partners to quickly find solutions and take action What You’ll Own: Payroll Administration You will fully own payroll across multiple entities and pay groups, including: Own end-to-end payroll processing across multiple entities and pay groups Manage payroll inputs, uploads, and approvals to ensure timely and accurate payroll Maintain PTO accruals and payroll records Process off-cycle payrolls (bonuses, commissions, PTO payouts, corrections) Provide payroll reports to 401(k) and HSA vendors Payroll Review, Validation & Reconciliation Perform pre-payroll checks to ensure readiness and accuracy Perform post-payroll validations to confirm payroll processed as expected Ensure payroll deadlines are met across all pay groups Reconcile payroll data across systems Track, manage, and clear unresolved items and variances , ensuring all discrepancies are followed through to resolution Payroll Tax Compliance Monitor federal, state, and local payroll tax filings and payments Maintain a centralized tracker of payroll tax accounts across entities and states Identify and address discrepancies, including tax notices, account gaps, or filing misalignments Coordinate with payroll providers and agencies to ensure timely resolution and compliance Benefits Administration & Reconciliation Manage benefits administration in Employee Navigator and ensure alignment with payroll systems Audit benefit rates and deductions for accuracy Reconcile benefit invoices against payroll deductions and employer contributions Support Open Enrollment in partnership with the VP of People Partner with brokers and vendors to resolve discrepancies Lifecycle Management Ensure accurate payroll and benefits setup for new hires Manage offboarding processes, including: Final pay compliance (state-specific) PTO payouts Benefits termination and COBRA coordination Employee Support & Operations Serve as primary point of contact for payroll and benefits inquiries Manage Zendesk tickets and internal requests Escalate complex issues and ensure timely resolution What You’ll Build & Improve (Critical Part of the Role) This role is not just execution - you are expected to build structure. Process & Systems Development Document processes Develop trackers Standardize workflows Maintain organized and audit-ready documentation Data Cleanup & Operational Fixes Ongoing & Cross-Functional Projects Benefits vendor transitions and system integrations Special compensation or benefits programs What This Role Requires 2+ years of payroll and/or benefits experience Strong Excel and reconciliation skills High attention to detail and accuracy Ability to manage multiple deadlines and priorities Strong problem-solving and ownership mindset Comfortable working cross-functionally with Finance, HR, and external vendors Experience with Rippling or similar HRIS/payroll systems is a plus What Will Make You Successful Here You take ownership beyond task execution and follow through on issues You are comfortable working in an evolving, fast-paced environment You can identify gaps and proactively improve processes You stay organized and maintain clear documentation and trackers You communicate effectively and escalate risks early If you are excited to take ownership, build structure, and make a meaningful impact, this role is a great fit. About Us Parallel is the first tech-forward provider of care for learning and thinking differences across the United States. We believe learning differences are parallel ways of thinking that should be celebrated! Our mission is to provide students with the resources and encouragement to succeed in the classroom and beyond. To us, this means helping them build confidence in their unique strengths and create strategies to work around their challenges. Parallel simplifies the process of getting support for learning differences by consolidating providers and resources on a single platform. We connect students with qualified professionals while significantly reducing waiting times, costs, and confusion. We provide a variety of services, including: Psychological Assessment & Therapy Counseling Speech-Language Therapy Special Education And more! Want to know what it's like working here? Check out our Glassdoor reviews! Our commitment to diversity, equity, and inclusion At Parallel, we believe in celebrating differences. This belief extends from schools into our workplace and through the ways we work together toward our mission. We are committed to fostering a diverse, accessible environment that represents many different cultures, backgrounds, viewpoints, and abilities by championing diversity, equity and inclusion. This is why we are committed to having and fostering a diverse workforce, including those from historically marginalized groups, and are committed to a work environment where employees’ strengths are championed, differences are celebrated, and no one is discriminated against based on age, race, ancestry, religion, sex, gender identity and expression, sexual orientation, pregnancy, marital status, physical or mental disability, military or veteran status, national origin, or any other characteristic. We are a proud equal opportunity employer, and we are committed to building a diverse, equitable, and inclusive organization in order to build the foundation for different learners and thinkers to thrive. By providing a telephone number and submitting the form you are consenting to be contacted by SMS text message. Message & data rates may apply. Reply STOP to opt out of further messaging.