Payroll and Benefits Specialist

About Us: Headquartered in Chicago, Performance Trust Capital Partners, LLC is an investment bank that combines Wall Street scale with the agility of an independent, employee-owned firm. We help financial institutions uncover overlooked opportunities, navigate complexity, and make decisions grounded in insight—not impulse. Our work is focused on long-term impact and relationships built on what matters most: trust and enduring performance.

About the Position: Reporting to the SVP of HR Operations, the Payroll and Benefits Specialist is responsible for running payroll, administering benefits, and supporting broader HR operations as the firm grows, including HRIS management, ESOP administration, employee support, and UK payroll.  

This role is well-suited for someone who thrives in a high-volume, deadline-driven environment, manages competing priorities independently, and holds themselves accountable to a high standard of accuracy and follow-through. Performance Trust is growing quickly, and this role will expand with it, including exposure to international payroll and the opportunity to shape how HR operations scale. 

Please Note: While we love connecting with curious candidates, we want to be transparent that informal conversations with our team do not factor into hiring decisions. The best way to move forward is to apply directly as we review every application carefully.  

Specifically, this individual will be responsible for the following: 

Payroll Administration 

• Process semi-monthly payroll accurately and on time, managing the full cycle from pre-processing through submission, audit, and final confirmation.  
• Administer new hire and termination payroll actions, including partial pay calculations, tax setup verification, and benefit deduction adjustments.  
• Manage post-payroll responsibilities each cycle, including 401(k) funding, HSA uploads, and confirmation to Finance and relevant stakeholders.  
• Administer benefit deductions each pay period, including FSA, commuter benefits, and 401(k) contributions, ensuring accuracy and compliance with IRS limits.  
• Maintain multi-state payroll compliance, including tax jurisdiction setup, address change processing, and regulatory notifications.  
• Prepare and maintain payroll records, reports, and documentation in support of audits, tax filings, and year-end W-2 preparation.  
• Serve as the primary point of contact for employee payroll questions, including pay inquiries, paystub requests, and communication on anything affecting an employee's check.  
• Compile and deliver payroll reports for Finance, HR leadership, and other internal stakeholders as requested.  
• Respond to inquiries from government agencies, Finance, and auditors, and support documentation requests related to payroll compliance and reporting.  
• Support UK payroll administration and contribute to payroll setup in new countries as the firm expands. 

Benefits Administration  

• Administer day-to-day benefits including enrollments, changes, terminations, billing audits and COBRA, ensuring accuracy and timely processing across all plans. 
• Lead open enrollment end to end, including plan setup, premium updates, carrier file feed management, employee communications, and training sessions.  
• Serve as the primary point of contact for all benefits questions and claims escalations, providing responsive and knowledgeable support to employees at all levels.  
• Present benefits during new hire orientation and serve as an ongoing resource for employees navigating their coverage.  
• Administer the 401(k) plan including enrollment, contribution changes, loans, rollovers, distributions, required notices, and census reporting; participate as a member of the 401(k) committee.  
• Administer the firm's Employee Stock Ownership Plan (ESOP), including enrollment, policy management, distributions, census reporting, and employee education on the benefit.  

HRIS Administration  

• Maintain workforce data in Paylocity, ensuring confidentiality, accuracy, and data integrity through periodic audits.  
• Process HR transactions in a timely manner: separations, transfers, promotions, and compensation changes.  
• Prepare ad hoc and recurring reports for HR leadership and the executive team.  
• Serve as a resource to employees and managers for Paylocity technical support.  
• Identify manual or inefficient processes and build workflows, automations, and documented procedures that scale as the organization grows.  

 Employee Support & HR Operations  

• Serve as a knowledgeable and responsive first point of contact for employee and manager questions on HR practices, policies, and procedures.  
• Process and track employee time-off requests with accuracy and follow-through.  
• Maintain employee and HR records in compliance with federal and state laws.  
• Collaborate with teammates to support broader HR priorities and pivot outside of core responsibilities as business needs arise. 
• Complete ad hoc projects and initiatives at the direction of the Chief Human Resources Officer or SVP of HR Operations. 

We are seeking candidates with the following qualifications:

• Bachelor's degree required; professional HR certification (PHR/SPHR) preferred.  
• Five or more years of relevant experience, preferably with exposure to multiple HR functions.  
• Deep knowledge of payroll concepts and multi-state payroll processing; end-to-end ownership experience required.  
• International payroll experience strongly preferred; willingness to support new country setup as we expand into the EU.  
• Prior experience with a cloud-based HRIS required; Paylocity experience strongly preferred.  
• High degree of comfort with technology, including strong Excel skills and proficiency across Microsoft Office; capable of learning and mastering new platforms quickly. 
• Exceptional organizational skills; able to manage a large volume of concurrent deadlines and responsibilities.  
• Discretion and composure when handling sensitive or complex employee situations.  
• Strong interpersonal skills and a collaborative orientation.  
• Commitment to continuous professional growth and development. 
• Candidates must be eligible to work permanently in the United States without sponsorship.

Featured Benefits

Health Coverage

• Medical, Dental & Vision Insurance (administered through a national carrier such as Blue Cross Blue Shields )
• Prescription Drug Plans
• Pre-Tax Flexible Spending Account (Health and Dependent Care) (FSA)
• Health Savings Account (HSA)

Time Off & Work-Life Benefits

• Vacation/Personal Days + Holidays
• Financial & Income Protection Benefits
• PT Retirement
• Mission-Driven Employee Stock Ownership Plan
• Voluntary Life Insurance + Long-Term Disability Insurance

Wellness & Everyday Support

• Discounted Fitness Memberships (Free membership for Chicago office)
• Pre-Tax Commuter Benefits – Transit & Parking
• Mental Health support through company provided Employee Assistance Program
• Employee recognition programs (PT Rewards and Annual Awards) 

Compensation: The base salary range for this position is $90,000-$120,000.This is an estimated range based on the circumstances at the time of posting, however, may change based on a combination of factors, including but not limited to skills, experience, education, market factors, geographical location, budget, and demand. This position is also eligible for a bonus component that would be dependent on pre-defined performance factors. All compensation determinations are based on the skills and experience required for the position and commensurate with experience of selected individuals, which may vary above and below the stated amounts. 

For Recruitment Agencies: As our recruitment is primarily handled in-house, we work only occasionally with external agencies, and only those on our existing, pre-approved vendor list. At this time, we are not reviewing or expanding that list. Unsolicited agency resumes, emails or other channels of outreach will not be reviewed. Unsolicited resumes or submissions from external agencies not authorized by our Talent Acquisition team will be considered direct candidate applications. As such, Performance Trust will not assume responsibility for any placement fees associated with these submissions. Outreach to individual employees outside this process will result in permanent removal from consideration for any future approved vendor relationship.