Senior Associate, Benefits & Payroll

About Clear Street:

Clear Street is modernizing the brokerage ecosystem. Founded in 2018, Clear Street is a diversified financial services firm replacing the legacy infrastructure used across capital markets. 

We started from scratch by building a completely cloud-native clearing and custody system designed for today’s complex, global market. Our platform is fully integrated with central clearing houses and exchanges to support billions in trading volume per day. We’ve agonized about our data model abstractions, created horizontal scalability, and crafted thoughtful APIs. All so we can provide a best-in-class experience for our clients. 

By combining highly-skilled product and engineering talent with seasoned finance professionals, we’re building the essentials to compete in today’s fast-paced markets.

The Role:
As a Benefits & Payroll at Clear Street, you will play a key role in delivering a best-in-class employee experience by managing and supporting our benefits programs while assisting with payroll operations. Your focus will be on administering health, retirement, and wellness benefits, ensuring compliance, and serving as a trusted resource for employees. You will also provide payroll support in partnership with our Finance, Tax, and People Operations teams, ensuring accurate and timely processing. This role requires strong attention to detail, vendor management skills, and a deep interest in helping employees understand and maximize their total rewards.

Responsibilities:

• Administer and maintain all employee benefits programs, including health, dental, vision, retirement, life insurance, commuter benefits, and wellness offerings.
• Partner with our Chief People Officer to design and maintain competitive benefits programs that align with Clear Street’s culture and the market.
• Lead the annual benefits plan design, open enrollment, and all related employee communications.
• Manage day-to-day relationships with benefits vendors, escalating and resolving issues as needed to ensure service quality.
• Serve as the first point of contact for employees on benefits questions, policies, and enrollment support.
• Assist in administering payroll processes by ensuring data accuracy, reviewing entries, and coordinating with Finance and Tax to meet compliance requirements.
• Support payroll reporting for internal and external needs (including year-end filings and W-2 issuance).
• Help document and maintain standard operating procedures for payroll and benefits processes.
• Research and provide guidance on benefits and payroll considerations when entering new geographies or expanding operations.
• Collaborate with People Operations, Talent Acquisition, and Finance to align benefits and payroll with Clear Street’s overall total rewards strategy.
• Participate in ad hoc People Operations projects and initiatives as assigned.
  
  

Requirements:

• 3–5 years of experience in benefits administration, with exposure to payroll support.
• Strong knowledge of health and welfare benefit programs, including healthcare, retirement, life, and wellbeing benefits.
• Familiarity with payroll operations, including compliance with federal, state, and local labor/tax laws.
• Experience managing third-party benefits and payroll vendors.
• Proficiency in HRIS systems (UKG Ready preferred).
• Excellent organizational skills, attention to detail, and discretion when handling confidential data.
• Strong interpersonal and communication skills with the ability to provide clear guidance to employees.
• Problem-solving mindset, curiosity to improve processes, and ability to manage competing priorities.
  
  

.

We Offer:

The Base Salary Range for this role is $100,000-$125,000. This range is representative of the starting base salaries for this role at Clear Street. Where a candidate falls in this range will be based on job related factors such as relevant experience, skills, and location. This range represents Base Salary only, which is just one element of Clear Street's total compensation. The range stated does not include other factors of total compensation such as bonuses or equity.

At Clear Street, we offer competitive compensation packages, company equity, 401k matching, gender neutral parental leave, and full medical, dental and vision insurance. Our belief has always been that we are better as a business when we are all together in person. We are requiring employees to be in the office 4 days per week. In-office benefits include lunch stipends, fully stocked kitchens, happy hours, a great location, and amazing views.

Our top priority is our people. We’re continuously investing in a culture that promotes collaboration. We help each other through challenges and celebrate each other's successes. We believe that modern workplaces succeed by virtue of having high-performance workforces that are diverse — in ideas, in cultures, and in experiences. We put in the effort to make such a workplace a daily reality and are proud to be an equal opportunity employer.  #LI-HYBRID