People Operations Specialist at Thoughtful

About Thoughtful AI

Thoughtful AI is on a mission to redefine how intelligent technology empowers businesses. As part of our fast-growing team, you'll have the opportunity to shape the future of work while supporting a world-class employee experience. Our people are our greatest asset—and we're looking for a People Operations Specialist who’s passionate about building scalable, employee-centric systems and processes.

Learn more about our Warrior culture.

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About the Role

We’re seeking a detail-oriented, systems-savvy People Operations Specialist to help us deliver a seamless and high-impact employee experience across the full lifecycle—from onboarding to offboarding and everything in between. In this role, you’ll be the backbone of our People Operations function, supporting HR systems, benefits, payroll, compliance, and internal programs that keep our organization running smoothly.

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Key Responsibilities

Employee Onboarding & Systems

• 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.

HR Systems and Records Management

• 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.

Payroll, Benefits & Leave

• 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.

Employee Experience & Operations

• 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.

Performance & People Programs

• Support performance management cycles in partnership with leadership.
• Support and/or manage employee relations cases, including performance issues, investigations, and terminations.

Events & Culture

• Support execution of company-wide events such as TKOs and team gatherings that drive engagement and alignment.

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What You Bring

• 2+ years of experience in HR, People Operations, or a related field.
• Familiarity with tools like Gusto, Greenhouse, Notion, and Clerky preferred.
• 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.

Thoughtful AI Benefits

• Market-leading base salary
• 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