People Operations / Payroll Specialist

Who we are: 

At SpotHero, we work as a team to empower people to get everywhere, easier! We’re rapidly growing with the mission of bringing the parking industry into the future through technology. Drivers across the nation use the SpotHero mobile app or website to reserve convenient, affordable parking in advance, on-the-go, or through their connected cars, and parking companies rely on us to help them reach new customers while optimizing their business. We connect the dots with cutting-edge technology, delivering value to both sides of this exciting, evolving marketplace. We’ve been quite busy; take a peek at some of our recent announcements.

People Operations Specialist at SpotHero: 

The People Operations Specialist plays a key role in delivering a seamless, compliant, and high-quality employee experience across SpotHero’s US and Canadian workforce. This role owns the execution of payroll, benefits, leave, and core employee lifecycle operations, while partnering closely with People Leadership to ensure accuracy, compliance, and continuous improvement. With a strong focus on systems, data, and process optimization, this individual helps scale People Operations and enhance how we support employees across the organization.

What you will do:

Payroll (U.S. & Canada)

• Own end-to-end payroll processing for U.S. and Canadian employees, ensuring accuracy, timeliness, and compliance across all pay cycles
• Process payroll changes, including new hires, terminations, compensation updates, bonuses, and deductions
• Partner with People Leadership to reconcile payroll each cycle, validate outputs, and ensure accuracy prior to finalization
• Audit payroll data, investigate discrepancies, and proactively resolve issues
• Identify trends or recurring issues across payroll cycles and recommend process improvements to enhance accuracy and efficiency
• Ensure compliance with U.S. federal/state and Canadian federal/provincial payroll regulations
• Support payroll reporting, accruals, and audit readiness

Benefits, Leave & Wellness Administration

• Administer employee benefits programs (health, retirement, wellness) across the U.S. and Canada, ensuring accurate enrollment, employee support, deductions, audits, and reporting
• Manage leave of absence programs in compliance with federal, state, and provincial regulations, partnering with employees and managers throughout the process
• Support and execute open enrollment, including employee communications, vendor coordination, and system updates
• Review and validate benefit invoices and ensure alignment with payroll and vendor data
• Develop and enhance wellness initiatives that support employee well-being
• Identify opportunities to improve benefits and leave processes, ensuring compliance while elevating the employee experience

People Operations & Administration

• Manage and optimize the People Team service desk, delivering a high-quality, responsive support and track and report on metrics to ensure a five-star employee experience
• Own onboarding and offboarding processes, ensuring a seamless, consistent, and heroic employee experience across the lifecycle
• Maintain the org charts and ensure accurate employee data for integrity across HR systems
• Ensure People Operations practices comply with U.S. federal and state employment laws and Canadian federal and provincial regulations, including proper documentation and recordkeeping
• Partner with Legal, Finance, and People Leadership to support compliance initiatives, audits, and policy adherence
• Serve as a trusted resource for employees and managers, providing timely, thoughtful support
• Build and maintain people and payroll reports (headcount, turnover, compensation, etc.)
• Translate data into insights to support People Team and business decisions
• Develop expertise in HRIS and payroll systems; support ongoing optimization and enhancements
• Identify inefficiencies and implement scalable, compliant process improvements across People Operations
• Document and maintain clear SOPs to ensure consistency and operational excellence
• Partner cross-functionally with Finance, IT, and Legal to streamline workflows and improve systems

Who you are: 

• You are Collaborative & Service-Minded – You genuinely care about our people and take pride in your work. You build strong relationships across teams and are passionate about delivering a responsive, thoughtful, and five-star employee experience
• You are Trustworthy – You handle sensitive and confidential employee information with discretion, professionalism, and sound judgment, maintaining appropriate confidentiality at all times
• You are Detail-Oriented & Accountable – You take ownership of critical processes like payroll and ensure accuracy every time, knowing the details directly impact the employee experience
• You are a Systems Thinker – You see how processes connect and are always looking for ways to make People Operations more seamless, scalable, optimized, and employee-friendly
• You are Curious & Analytical – You ask questions, explore data, and uncover insights that help improve how we support our employees
• You are Adaptable & Proactive – You thrive in a fast-paced environment, anticipate needs, and take initiative to solve problems before they impact the employee experience

What you bring: 

• 3+ years of experience in People Operations, HR, or a related field in mid-sized SaaS, Technology, Marketing or similar industries
• Direct experience processing multi-state, multi-country payroll (U.S. required; Canada strongly preferred and payroll certification a plus)
• Experience administering benefits and managing leave of absence processes in conjunction with additional people programs (i.e. wellness, recognition)
• Knowledge of U.S. payroll regulations and familiarity with multi-country requirements (Canada preferred)
• Working knowledge of U.S. employment laws (federal and state) and exposure to employment regulations outside the US (Canada preferred)
• Experience with Payroll, HR, and Benefits systems (ADP WorkforceNow and TeamPay strongly preferred)
• Strong analytical skills and comfort working with data (Excel/Google Sheets required)
• High attention to detail and a commitment to accuracy
• Reliability with using sound judgement in handling sensitive and confidential information
• Ability to communicate effectively in a clear, professional, and approachable way
• Ability to manage multiple priorities in a fast-paced environment

Seeking Candidates in: 

• Chicago, IL - 1 day per week in office 

What we are offering:

• Career game changer – A truly unique experience to work for a fast-growing company in a role with unlimited growth potential.
• Excellent benefits
  • We cover a generous portion of Medical Premiums, 50% of Dental and Vision Premiums, company-sponsored Life Insurance, STD, and AD&D coverage, a 401(k) with match and immediate vesting, and comprehensive leave policies to meet your needs in creating space for life.
• Flexible PTO policy and outstanding work/life balance – We value and support each individual team member.
• Grubhub weekly lunch stipend for in-office days
• Udemy License and Personal Learning Budget – We support the professional and personal growth of our people by providing everyone with learning resources and development opportunities.
• Annual parking stipend – Duh. We help people park!
• The opportunity to collaborate with fun, innovative, and passionate people in a casual yet highly productive atmosphere.
• Our commitment to allyship has been a central driver of how we Respect Fellow Drivers. You’ll have the opportunity to be part of Employee Resource Groups, access allyship learning resources, and actively contribute to our ongoing effort of making SpotHero inclusive for all.
• Employee programs to grow and support our people such as Discovery Days for Product and Engineering, Gearing up for Aspiring Leaders, and Mentorship Program.
• Wellness program – a workplace that actively supports your physical and mental wellbeing through ongoing events, initiatives, resources, and thoughtful perks and benefits.
• A workplace recognized as CityLights award winner by 1871, 2026 Best Places To Work by BuiltIn, Most Loved Workplace Certified by the Best Practice Institute, and recipient of multiple Comparably awards, including Best Company Culture, Best Company for Women, and Best Company for Diversity.

Compensation in Illinois:

Depending on your skillset and experience, you can expect your base salary to be between $65,920 - $90,000 as well as a discretionary bonus and leading total rewards package.

At SpotHero, we Respect Fellow Drivers by providing an inclusive interview experience for everyone, including people with disabilities. We are happy to provide reasonable accommodations to candidates in need of individualized support during the hiring process. Please let our team know of your need when you apply or as you begin interviewing with our team.

SpotHero is an equal opportunity employer. We know that a diverse workforce is the strongest workforce, and are committed to building and supporting an inclusive environment for all.Additionally, because we want to Remember to Signal, if you choose to provide us personal information in connection with a job application, please review our Applicant Privacy Notice which provides details about what information we collect and process about you in order to consider your candidacy.

PLEASE NOTE: This position is ineligible for visa sponsorship. To be considered for this role, you must be legally authorized to work in the US and not require sponsorship for employment now or in the future.