People Operations Specialist

Summary

Join Thoughtful AI as a People Operations Specialist and contribute to a seamless employee experience. You will be responsible for managing HR systems, benefits, payroll, compliance, and internal programs. Key responsibilities include employee onboarding, I-9 processing, background checks, managing offer letters, maintaining employee records, administering payroll and benefits, supporting leave management, and assisting with employee relations. You will also support company events and contribute to the ongoing improvement of internal processes and documentation. This role requires strong communication, project management, and systems thinking skills, along with experience in HR or a related field. Thoughtful AI offers a competitive salary, bonus, stock grants, and comprehensive benefits.

Requirements

• 2+ years of experience in HR, People Operations, or a related field
• Detail-oriented and process-driven, with a strong sense of ownership
• Ability to navigate sensitive and confidential information with discretion
• A systems thinker who loves to improve and document processes
• Strong communication and project management skills

Responsibilities

• Own and optimize the onboarding experience in Greenhouse, including automated communications and coordination with L&D and Workplace Experience
• Process and track I-9s, background checks, and laptop provisioning
• Manage offer letter and employment agreement workflows in Clerky, including equity and CIIA documentation
• Create and maintain legal employee folders and contractor documentation
• Serve as administrator for Gusto (payroll, benefits, time off), identifying and implementing process improvements
• Maintain accurate records in partnership with leadership
• Conduct regular audits and data cleanups across HR systems
• Administer payroll for employees and contractors in Gusto
• Support PTO and leave management, including FMLA, parental leave, and other types of absence
• Assist with benefits administration
• Support new hire orientation as needed
• Partner on Employee Handbook redesign and relaunch; build and maintain a Notion-based Employee Wiki
• Field and resolve ad hoc employee inquiries
• Support performance management cycles in partnership with leadership
• Support and/or manage employee relations cases, including performance issues, investigations, and terminations
• Support execution of company-wide events such as TKOs and team gatherings that drive engagement and alignment

Preferred Qualifications

Familiarity with tools like Gusto, Greenhouse, Notion, and Clerky preferred

Benefits

• Market-leading base salary and bonus
• Employee stock grants
• Medical, dental, and vision insurance for you and your dependents
• We expect you to unwind and disconnect for three weeks per year while still getting paid