Reports To: Human Resources Manager
Location: Milwaukee, WI (On-site)
Employment Type: Full-Time, Salaried, Exempt
About Wantable
At Wantable, we’re redefining retail through personalization. Our membership-based model and proprietary technology empower us to curate products that help customers discover confidence and joy through style.
As a data-driven fashion company, we combine human intuition with algorithmic intelligence to deliver personalized assortments – balancing creativity, analytics, and operational precision.
We're seeking a Senior HR Generalist - Payroll, Benefits & HRIS who serves as the subject matter expert and operational authority for multi-state payroll execution, benefits compliance governance, HRIS administration, and regulatory risk management at Wantable. This role owns the integrity, accuracy, and audit-readiness of payroll, benefits, and HR systems infrastructure.
About the Role
Operating with significant autonomy, the Senior HR Generalist - Payroll, Benefits & HRIS prepares and governs end-to-end payroll processing, fully owns open enrollment strategy execution, administers complex multi-state compliance filings, and leads HRIS configuration optimization. The Human Resources Manager serves as the final payroll reviewer; however, this role is accountable for the completeness, accuracy, and audit integrity of all underlying data and processes.
Success in this role is defined by measurable operational excellence, including:
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Achieving ≥98% payroll accuracy within the first 90 days and sustaining near-zero error processing thereafter.
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Maintaining 100% on-time submission of all federal and multi-state compliance filings.
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Achieving 100% accuracy in monthly carrier invoice reconciliation.
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Maintaining 100% HRIS employee data integrity across lifecycle events.
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Establishing and maintaining structured ACA, ERISA, and 401(k) audit schedules with zero missed deadlines.
This role combines deep regulatory knowledge, systems thinking, process transformation capability, and responsible automation adoption to safeguard organizational compliance while increasing operational efficiency.
What You’ll Do
Payroll Governance & Operational Authority
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Serve as the organizational subject matter expert for multi-state payroll administration (with an emphasis on CA, IL, MN, WA), ensuring regulatory compliance and tax accuracy.
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Own full-cycle bi-weekly payroll preparation from data validation through pre-submission audit, achieving ≥98% accuracy within the first 90 days and continuous improvement thereafter.
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Independently diagnose and resolve payroll discrepancies, tax variances, garnishments, and system errors; implement structural process improvements to prevent recurrence.
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Design and maintain documented payroll audit controls, reconciliation procedures, and redundancy safeguards.
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Prepare final exit payout statements for terminated employees and process back-end functions to ensure compliance with final pay regulations and internal controls.
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Identify and implement automation opportunities that reduce manual processing time, increase validation accuracy, and strengthen audit trails.
Benefits Governance, Strategy Execution & Regulatory Compliance
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Act as benefits administration subject matter expert and primary owner of open enrollment planning and execution.
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Partner strategically with brokers and senior leadership to evaluate plan design options, regulatory implications, and cost modeling before executive approval.
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Execute approved benefits changes with structured communication, compliance validation, and system integration.
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Reconcile carrier invoices monthly with 100% accuracy and proactively resolve discrepancies.
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Maintain full compliance ownership for ACA, COBRA, ERISA, OWBPA, Secure Act 2.0, and 401(k) audit requirements.
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Establish and manage recurring compliance calendars and audit documentation frameworks.
Compliance & Risk Mitigation Leadership
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Fully own all federal and state compliance filings, ensuring 100% on-time completion with zero missed deadlines.
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Manage unemployment claims, workers’ compensation documentation, employment verifications, and audit preparation.
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Monitor multi-state regulatory changes and proactively adjust payroll and benefits processes accordingly.
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Maintain a centralized compliance calendar with built-in redundancy controls.
HRIS Owner & Systems Optimization
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Serve as Paycom HRIS system owner, responsible for configuration integrity, permissions governance, workflow accuracy, and organizational structure alignment.
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Maintain 100% accuracy of employee records across onboarding, job changes, compensation updates, and terminations.
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Lead intermediate-level system enhancements to improve reporting efficiency, compliance tracking, and payroll precision.
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Build and maintain automated dashboards and compliance reporting tools (ACA, EEO-1, unemployment, workers’ compensation, 401(k).
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Will respond to all report requests and needs from the broader organization and will generate reporting out of the HRIS, Paycom.
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Introduce responsible AI-enabled validation tools and workflow automation to increase speed and reduce risk while maintaining data privacy standards.
Additional Functions
- Other duties as assigned. Duties, responsibilities and activities may change at any time with or without notice.
Requirements
What We’re Looking For
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Bachelor’s degree in Human Resources, or related field (or equivalent professional experience).
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5+ years of progressive experience in payroll administration, benefits compliance, and HRIS management.
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Demonstrated expertise administering complex multi-state payroll (emphasis on California, Illinois, Minnesota, and Washington).
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Hands-on audit and regulatory filing experience (ACA, ERISA, 401(k), EEO-1, unemployment, state/federal filings).
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Proven ownership of open enrollment planning and broker collaboration.
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Intermediate HRIS system administration experience (Paycom strongly preferred).
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Ability to translate complex payroll and regulatory information into clear, actionable guidance.
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Professional communication skills suitable for executive-level and vendor interactions.
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Confidence serving as subject matter expert for compliance-related inquiries.
Nice to have
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CEBS, GBA, or RPA certification
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Working knowledge of Apple technology.
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Familiarity with Google products (Drive, Gmail and Docs).
You'll Thrive Here If You
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View payroll and benefits infrastructure as business-critical risk management functions.
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Take pride in measurable precision and compliance reliability.
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Enjoy balancing regulatory depth with systems innovation.
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Operate with strong independent judgment and ownership.
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Embrace automation-first thinking while protecting employee trust and data integrity.
How We Work at Wantable
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High ownership. You are trusted to make decisions that directly impact customers and financial performance.
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Hard-working and hands-on. We move fast, stay scrappy, and focus on impact.
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Independent thinkers. We value leaders who confidently make data-driven decisions without layers of approvals.
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Low bureaucracy. We avoid committees, long processes, and unnecessary steps.
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Love of fashion & product. We combine data with intuition to create experiences customers love.
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Results over pedigree. What you’ve built matters more than where you’ve been.
Benefits
Why Wantable?
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Be part of a dynamic, fast-growing company that has innovation and creativity embedded in its DNA.
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A chance to shape our customers’ journey and leave a lasting impact on their self-confidence, one order at a time.
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Join a collaborative environment where your ideas matter, your efforts are rewarded and you can see results in real time.
We have a laid-back, casual environment in a state-of-the-art HQ in Walkers Point.
We offer flexible schedules, paid parental leave (mothers AND fathers), and a private room for nursing mothers.
Even more exciting: paid vacation and seven paid holidays per year, plus a 50% discount on all merchandise. You’ll be eligible for the discount on your first day.
Important, but maybe less thrilling: we have ample parking, we offer medical (traditional and high deductible), dental, and vision insurance, as well as a 401K (both pre-tax and Roth options).
