Remote job description

What we're building

Pilot is a tech company building the bookkeeping firm you wish existed. We deliver books and a customer experience of unparalleled quality by automating the boring stuff and equipping a team of finance experts with software superpowers to deftly handle the rest.

The team

We are a small but passionate team of 165+ based in San Francisco and Nashville. Pilot's seasoned founding team has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox). We give our employees a lot of responsibility and ownership of their work, and we hire people from a very wide range of backgrounds and experience. Our team members operate with a high degree of empathy for our customers and each other.

The role


  • Administer all activities relating to the company payroll, benefits and HRIS processing including developing, implementing and monitoring
  • Develop and implement scalable payroll and benefits processes to support Pilot's growth

Duties and Responsibilities


  • Manage Pilot's payroll function - ensure the timely and accurate processing of payroll including salaries, benefits, garnishments, imputed income transactions, taxes, and other deductions
  • Process payroll for hourly, salaried, and temporary employees; including reviewing and importing hours from time and attendance system, entering tax and direct deposit information, administering regulatory requirements, e.g., garnishments, tax levies, and support orders, and other adjustments to pay as necessary
  • Ensure pay is processed on time, accurately, and in compliance with government regulations
  • Respond to all unemployment claims and regulatory notices in a timely manner
  • Work with third party vendor to prepare and file quarterly employer tax returns
  • Prepare and maintain accurate records and reports of payroll transactions, including new hires, employee movements, terminations, and changes to pay rates
  • Ensure compliance with federal, state, and local payroll, wage, and hour laws and best practices
  • Ensure proper pay controls are in place
  • Facilitate audits by providing records and documentation to auditors
  • Implement and maintain payroll best practices to improve efficiency and consult with the People team to improve payroll and HRIS processes
  • Administer the time and attendance policy and paid leave policy for all employees
  • Produce scheduled and ad-hoc reports pertaining to payroll and HR requirements


  • Maintain complete electronic employee personnel files, records and other documentation for employees, including processing new employees, forms for employment status changes and maintaining timely and accurate files. Coordinate pre-employment paperwork and processes
  • Prepare statistical summaries and reports from the HRIS involving payroll information, performance management, demographic data and other employee data
  • Assist to maintain data integrity in HRIS systems by running queries and analyzing data and reviewing source documents for accuracy and completion of data input
  • Generate files/reports such as annual non-discrimination testing for benefits plans, annual reports, as well as other special and ad hoc reports as requested
  • Recommend business process improvements having an HRIS component

Benefits Administration

  • Plan and manage the day-to-day operations of group benefits programs
  • Handle enrollments, COBRA, terminations, changes, beneficiaries, disability, accident and death claims, and compliance testing
  • Serve as primary contact for plan vendors and third-party administrators
  • Leveraging industry trends, research current and potential employee benefit plans and vendors to identify those that present the best value
  • Design, recommend and implement new benefits programs. Examine possible plan designs and benefits cost changes
  • Negotiate with vendors and administrators for best plans, options and rates
  • Coordinate transfer of data to external contacts for services, premiums and plan administration
  • Evaluate and revise internal processes to reduce costs and increase efficiency
  • Document and maintain administrative procedures for assigned benefits processes
  • Ensure compliance with applicable government regulations. Ensure timeliness and accuracy of required reporting and fees
  • Perform plan audits as needed. Prepare, collect and organize data for actuarial assessments
  • Provide customer service support to internal and external customers. Develop communication tools to enhance understanding of the company's benefits package
  • Design and distribute materials for benefits orientations, open enrollment and summary plan descriptions

Experience and Requirements

  • Bachelor's degree (or above) in an HR- or Finance-focused field of study preferred
  • Experience working at a tech startup preferred
  • Knowledge of the various Human Resources disciplines preferred
  • Extensive knowledge and ownership of the payroll function in a fast paced organization, including preparation, balancing, internal control, and payroll taxes required
  • Proficient with ADP payroll software required
  • Experience administering benefits programs required
  • Knowledge of all pertinent federal and state regulations, filing and compliance requirements, both adopted and pending, affecting employee benefits programs preferred
  • Proficient with Microsoft Office Suite or related software
  • Strong communications and relationship building skills to effectively support and connect with a diverse team
  • Excellent written and presentation skills
  • Excellent organizational skills and attention to detail
  • Demonstrated success in meeting exceptionally high standards in a high volume, fast-paced & hands-on environment
  • Attention to detail; experience with people analytics, metrics and business consulting skills
  • Ability to diagnose problems with strategic thinking skills, as well as drive appropriate solutions with self-initiative
  • Understanding and ability to be highly productive and influential in a matrixed management environment

Benefits of working at Pilot

  • Medical, dental, and vision benefits
  • Holidays and flexible PTO
  • Paid family leave
  • Company sponsored 401(k) plan
  • Pre-tax commuter benefit
  • Convenient office location in San Francisco, (although currently the company is WFH due to COVID)
Company: Pilot
Job title: Lead, Payroll and Benefits Operations
Job tags: business services, saas / subscription, software
  • location or timezone

    San Francisco
  • category

    Human Resources
  • posted

    54 days ago

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