Note to Candidates:

We meticulously craft our job descriptions to clearly define the skills necessary for success and the expected performance level of the role, resulting in detailed content. Our goal is to ensure the description accurately reflects the job you will perform. We value your input and look forward to hearing what you think about the format in the interview process.

This is a hybrid role (three days per week at our HQ in Chicago, IL) and will report directly to the Director of Finance.

Who We Are:

Crafty elevates workplace food and beverage programs with enhanced services managed in one innovative, centralized platform. Founded in 2015, our mission is to help companies craft better workplaces. From DraftKings to Robinhood to Zillow, we work with the world's biggest brands to foster a culture of employee connectivity and productivity. Headquartered in Chicago, with offices in New York and the Bay Area, Crafty manages food and beverage programs across 300+ offices, serving more than 300,000 employees per month.

Our commitment to crafting better workplaces starts from within. We are a team of passionate, resourceful, and hard-working trailblazers who love what we do. Our expertise spans technology, food and beverage operations, client success, fulfillment and more. At Crafty, our people are our greatest asset, because it's our people who foster a culture that makes our company a place worth being part of. And of course, the snacks are the cherry on top!

The Role:

The Payroll Manager plays a critical role in ensuring our team members are paid accurately and on time while maintaining compliance with all tax and regulatory requirements. This position is essential to maintaining employee satisfaction and financial integrity across our organization as we continue to scale.

Crafty is seeking a Payroll Manager who will report directly to the Senior Accounting Manager. This role will not manage direct reports but will have ownership of our payroll system (Rippling) and all payroll processes.

The Payroll Manager will own end-to-end payroll processing across multiple states—especially high-risk jurisdictions like California and New York—ensuring absolute accuracy and full compliance with tax and employment regulations. They will also lead 401(k) plan administration and will serve as the primary administrator for our Rippling HRIS platform, managing system configuration, maintenance, and optimization to support our growing workforce.

Success in this role means developing efficient payroll processes, providing exceptional support to employees regarding payroll inquiries, implementing best practices for HRIS management, and contributing to strategic initiatives that improve our Finance and People Operations.

The ideal candidate is detail-oriented, discrete with confidential information, proactive in identifying process improvements, and able to work collaboratively across departments while maintaining a high level of accuracy in a fast-paced environment.

Required Attributes

Process Management: Ability to develop, document, and optimize payroll processes across multiple pay cycles while ensuring compliance and accuracy
Technical Proficiency: Strong experience with HRIS systems, preferably Rippling, including configuration, troubleshooting, and system optimization
Compliance Across Jurisdictions: Deep understanding of payroll compliance requirements in high-risk states like California, New York, and Illinois, with proven experience staying current on regulatory updates.
Meticulous Attention to Detail: Proven track record of accurate processing across large payroll volumes, with minimal to zero manual corrections
Problem-Solving: Skill in identifying and resolving payroll discrepancies promptly and accurately, with attention to root cause analysis
Data Leadership: Ownership of payroll data integration with HR, time-tracking, and benefits platforms to ensure a single source of truth and support downstream financial reporting
Communication: Excellent verbal and written communication skills to effectively explain payroll policies and respond to employee inquiries
Confidentiality: Demonstrated discretion in handling sensitive employee information and maintaining appropriate confidentiality
401(k) Plan Expertise: Demonstrated ownership of 401(k) administration including employee education, enrollment, contributions, distributions, and audit readiness

Ideal Experience

3+ years of experience in payroll administration with ownership of 401(k) administration and payroll compliance in California or other complex jurisdictions
2+ years of experience with Rippling or similar HRIS platforms
Experience working in a high-growth company environment
Demonstrated experience with multi-state payroll tax rules and registration requirements
Certification in payroll management (CPP or FPC) is a plus
Experience coordinating with external auditors on 401(k) plan audits and payroll-related audits.
Experience with 401(k) plan administration, including handling employee inquiries, processing distributions, and supporting annual plan audits

Don't meet all of the qualifications? We want you to consider all of your skills and experiences - both professional and personal- that would make you successful in this role. Although some qualifications are essential, others can be attained with time. We believe diverse perspectives, upbringings, and knowledge contribute to our strong company culture and we encourage you to apply.

Role Goals

Goal #1: By the end of the first quarter 2026, you will establish standardized processes for all payroll activities, as measured by a 99.5% accuracy rate in payroll processing and reduction in manual adjustments by 30%, resulting in improved efficiency, increased employee trust in payroll processes, and reduced downstream corrections for accounting and benefits reconciliation.
Goal #2: By the end of the first quarter 2026, you will optimize our Rippling HRIS system configuration, as measured by implementing at least 3 automation improvements, reducing administrative time spent on manual tasks by 25%, and creating a comprehensive system documentation library to support company growth and scalability.
Goal #3: Within the first year, you will develop and implement a payroll compliance framework, as measured by conducting quarterly audits with zero material findings, maintaining up-to-date state and local tax registrations for all jurisdictions, and providing quarterly compliance updates to the finance team to support our risk management objectives.
Goal #4: Within six months, you will enhance the 401(k) administration process by implementing efficient procedures for handling employee inquiries, ensuring accurate and timely processing of distributions, and supporting the annual audit process with complete and organized documentation, resulting in 100% compliance with regulatory requirements.

What we offer:

Our people mean everything to us. When you join Crafty, you're joining a team of passionate, smart, and supportive people who work incredibly hard and have a good time along the way.

We are proud to offer a compensation package that includes our Crafty healthcare plan, covering primary health, dental, and vision plans, 401k, paid time off, equipment certification courses, and parental leave. And, of course, it also includes Crafty-grade snacks, beverages, and fun events!

Lastly, this role offers a special opportunity: to have a major hand in shaping the future of a young, flourishing company. Your creativity, ambition, and work will steer the direction of our successes.

Our compensation amount for this role is targeted at $85,000-105,000 per year. Final offer amounts are determined by multiple factors including cost of living based on location, candidate experience and expertise, and may vary from the amounts listed above.

Crafty provides equal employment opportunities (EEO) to all employees and applicants for employment without discriminating against race, color, religion, sex, sexual orientation, national origin, age, disability or genetics.