Payroll and Benefits Manager

Remote /
G&A – People & Culture /
Full Time Exempt

The People & Culture team works tirelessly to attract, develop, engage and retain a diverse and high-performing pool of professionals by building a psychological safe, equitable and inclusive work environment by way of  infrastructure and impactful talent development programs that support our current and future people to be and become their best-selves. In supporting our people in their professional and personal growth, we directly support 15Five’s growth and success as a business.

The Payroll and Benefits Administrator is responsible for the administration of a regular multi-state, exempt and non-exempt payroll and commission processing on a semi-weekly basis. This role requires the highest level of integrity, proactivity and attention to detail in maintaining confidentiality, accuracy,  and compliance of all payroll and benefits administration and reporting . The Payroll and Benefits Administrator is a critical role to the day-to-day operations of the company, interacting daily with Senior Leadership, People Operations, Finance and Accounting Leaders.


    • Payroll Administration for W2 Employees and 1099 Contractors (40%) 
    • Benefit Administration (40%)
    • 401K Administration (10%)
    • Partner to Accounting and Operations (10%)

    • Payroll Administration
    • Process regular exempt and non-exempt payroll on a bi-weekly basis, including commissions, special bonus or variable compensation payouts and off-cycle payrolls
    • Process all payroll changes, increases, corrections and adjustments with proper documentation and approvals from SLT, direct manager(s), and accounting partners
    • Maintain timely and accurate record keeping systems for FTO,  sick leave and other leave accruals
    • Process, administer and oversee all leave of absence-related payroll
    • Collaborate with multiple departments for onboarding and offboarding of employees and contractors including maintaining final paycheck compliance
    • Track and audit timecards for non-exempt employees
    • Provide detailed payroll reporting for finance and management
    • Serve as Company point of contact to Payroll technology platform team, Paylocity
    • Provide excellent customer service and timely responses to employee issues and inquiries regarding payroll payroll questions. Serve as the team’s Subject Matter Expert for answering complex payroll related questions to leadership
    • Develop and run reports to meet various levels of management requests for payroll related informationAccurately prepare and file all required Federal, State and Local reporting by due dates
    • Draft error free employee documents as necessary (e.g., offers, addendums, payroll updates, etc.)
    • Ensure compliance with federal and state wage and hour laws. Audit meal and rest breaks for hourly workers. 
    • Maintain up-to-date and completely accurate data in HRIS, compensation, onboarding, and other technology platforms
    • Support annual, quarterly, and monthly board, city, state, and federal required reporting
    • Work on special projects, audits, mandatory notices, compliance reporting and other administrative duties as needed 
    • Manage the wage garnishment process, preparing required paperwork as needed
    • Have a working knowledge on current state and federal payroll compliance requirements

    • Benefits Administration
    • Process new hires’ benefit elections
    • Be the primary go-to person and Subject Matter Expert for all benefits related issues, including Benefits Plan renewals 
    • Field general benefits questions, and serve as the Subject matter Expert for answering complex benefits related questions
    • Coordinate daily benefits processing: process enrollments, qualifying life events, terminations, COBRA, demographic/employment changes and beneficiary updates 
    • Regularly conduct audits and reconcile benefit invoices for timely submission to the Accounting Team
    • Regularly conduct benefits deductions audits to ensure compliance and accuracy
    • Process and manage leave of absence benefits according to local jurisdictions
    • Process, administer and oversee all leave of absence and accommodation requests and disability paperwork: medical, personal, disability, Federal & State mandated leaves (COBRA, FMLA, CFRA, PDL, ADA, FFCRA, EDD, FLSA, FEHA, HIPAA, EEO, ACA, SFHCSO).
    • Lead the facilitation of annual Company open enrollment
    • Lead the annual ACA auditing, reporting and filing process for 1095-C and other ACA forms
    • Serve as Company point of contact for benefits brokers, service providers and carriers
    • Maintain clean and excellent data  
    • Continue to conduct regular insurance invoice reviews 

    • 401K Administration
    • Conduct weekly audits of 401K deferral changes and ensure that all deductions are accurate and up to date
    • Lead and submit Annual form 5500 filing for 401K Plan
    • Conduct ongoing compliance testing for 401K Plan
    • Serve as Company point of contact for 401K service provider

    • Partner to People Operations, Accounting and Finance
    • Work on special projects, audits, mandatory notices, compliance reporting and other administrative duties as needed
    • Complete annual Workers Compensation audits 
    • Lead annual Workers Compensation policy renewal 
    • Organize and store all employee information and documentation with 100% accuracy
    • Support documentation of all departmental processes, compliance, and workflows
    • Run salary benchmarking reports in Payscale and gather research for Department heads


    • 4+ years experience with multi-state exempt and non-exempt W2 payroll processing and 1099 contractor payment processing
    • Previous experience with managing and auditing 401K retirement programs
    • Strong accounting and mathematical skills, advanced Excel skills for merging data from multiple sources  (filters, sorting, pivot tables, V lookup, etc.)
    • Prior experience managing ATS or HRIS system implementations from start to finish
    • Have a confident working knowledge with HR technology including various options for software that manages payroll, benefits, 401(k)
    • Exceptional attention to detail with ability to manage and process large volume of data with speed and accuracy
    • Highly organized and and committed to following strict processes and document storage protocols
    • Warm and helpful, service-oriented attitude 
    • Able to manage multiple deadlines and priorities and thrive in a fast-moving environment
    • Strong communication skills (verbal and written) 
    • Ability to handle sensitive employee information with strict adherence to confidentiality protocols
    • Able to prioritize, self-start and self-direct work with minimal direction 
    • Ability to solve complex problems or business challenges independently due to resourcefulness and subject matter expertise
    • A team player who genuinely enjoys approaching their work with an entrepreneurial and collaborative spirit


    • Successfully run W-2 payrolls and 1099 Contractor payments without supervision. Ensure new employees are set up correctly in payroll, enrolled in benefits, and have W4’s/state tax forms completed
    • Create and execute a strong working relationship and regular scheduled meetings with Propeller 
    • Identify areas within payroll and benefits program that may need improvement 
    • Identify and execute an ongoing strategy and working relationship with HRIS Analyst with the support of the Business Partners
    • Along with the People Operations Business Partner and the Finance Manager, identify key areas for improvement relating to commission payouts
    • Create and roll out an annual calendar of administration for your area and coordinate with all relevant parties
    • Complete all State Tax registrations, including a well-organized database of all documentation and records


    • Successfully inherit and execute leave of absence requests, current and upcoming 
    • Complete mid-year 401K audit
    • Identify needs for the benefits program for the upcoming Open Enrollment and work with the Sequoia Advocate team for upcoming market shopping
    • Provide all 15Fivers with a Total Rewards and Benefits Statement 


    • Partner with appropriate team members in preparing for company-wide annual compensation reviews 
    • Contribute and participate in budget planning meetings accordingly 
    • Complete Open Enrollment period and all employee elections in payroll and with insurance providers
    • Review 401K plan summaries, any distributions and/or rollovers, and complete EOY true-up audits and report to finance and accounting teams


    • Monday: Monday Boost meeting, respond to a expected minimum of 5 inquiries related to payroll/benefits, make several payroll updates for upcoming payrolls
    • Tuesday: Weekly POps team meeting(s), 1:1 with manager, work on payroll updates for first review, perform work for LOA case(s) whether it is a meeting or processing current benefit calculations
    • Wednesday: Wednesday Boost meeting, follow up with possibly 2-4 employees regarding payroll/benefits updates, make any changes accordingly, run a couple of ad hoc reports for POps team and/or SLT, conduct monthly audit of insurance provider invoices for new hires/separations
    • Thursday: Final payroll review and submission before morning deadline, download appropriate payroll reports and share with accounting team, process new payroll addendums for upcoming payrolls, process any terminations to benefit providers
    • Friday: Question Friday Boost, review 401K submission between Paylocity and Ubiquity, update state tax rate updates if needed, conduct annual reports if needed, complete weekly 15Five


    • Open to vulnerability, self-reflection, and candid feedback to grow personally and professionally
    • Curious and committed to innovation, continuous learning, and growth 
    • Self-motivated, self-responsible, and self-accountable

15Five is a people and performance platform that instantly upgrades each and every manager. It works by combining employee engagement, continuous performance management, and manager effectiveness software with education, services, and community. At the heart of our approach is Best-Self Management, an evidence-inspired strategy for cultivating world-class managers and transforming organizations by unlocking every employee’s potential. With our holistic solution, CEOs, HR leaders, and managers create highly-engaged, high-performing organizations.  

We work with over 2,000 forward-thinking companies that use our solution to bring out the best in their people, including big brand names like Credit Karma, WP Engine, Adobe, and Fitbit. 15Five is backed by Next 47, Origin Ventures, Point Nine Capital, and Matrix Partners. Its headquarters are based in San Francisco, with offices in New York and Raleigh, NC. The company is working 100% remotely during the COVID-19 pandemic.

We’re excited to continue building out a diverse team that prioritizes inclusivity and celebrates everyone’s unique identity. To support our people, 15Five believes in flexible working arrangements, non-gendered Parental Leave, Flexible Time Off, Sick Time Off and extensive training and development including but not limited to Diversity, Equity & Inclusion, Best-Self Management, strengths discovery and alignment and Manager specific development opportunities.

Research shows that while men apply for jobs when they meet an average of 60% of the criteria, womxn and other underrepresented folx tend to only apply when they check every box. So, if you think you have what it takes but don't necessarily meet every single point listed below, please apply - you could be exactly who we are looking for!

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