People Operations Generalist (6 month contract with possibility of contract-to-hire)

About the Role

The People Operations Generalist Contractor owns the day-to-day employee experience; from onboarding through development and retention, ensuring every employee feels supported, engaged, and set up for success.

As webAI scales beyond 200 employees, this role is critical in evolving People Operations into a strategic function. You will drive consistency, improve systems and processes, and partner with leaders to strengthen culture and performance across a growing, distributed team.

This is a highly cross-functional role that blends employee experience, operations, and manager support, while working closely with Legal & Compliance on clear escalation pathways.

This is a 6 month contract with possibility of contract to hire

Key Responsibilities

• Serve as a day-to-day People Operations resource for employees and managers during the leave coverage period.
• Respond to employee questions regarding company policies, benefits, leave, workplace practices, and general HR matters.
• Provide managers with guidance on routine employee relations matters, policy interpretation, attendance concerns, documentation, and employee issues.
• Support employee relations matters, including gathering information, documenting concerns, and escalating complex or high-risk matters to the VP of Operations and appropriate leadership.
• Support employee offboarding, including resignations and terminations, required communications, and coordination with the People Operations Support Specialist and other internal teams.
• Support benefits administration by assisting employees with benefits questions, qualifying life events, and vendor-related issues.
• Support employee leave administration, including employee communication, documentation requirements, and coordination with applicable vendors.
• Assist with employee changes such as promotions, compensation adjustments, title changes, transfers, and other employment updates.
• Provide HR guidance and support to the People Operations Support Specialist as questions or more complex situations arise.
• Partner with the VP of Operations on People-related matters requiring additional HR experience or judgment.
• Coordinate with Finance, IT, Recruiting, Legal, and department leaders as needed on employee matters.
• Support ongoing employee engagement, culture, recognition, and People Operations initiatives already in place.
• Assist with HR reporting, compliance requests, and other People Operations needs that arise during the coverage period.
• Maintain confidentiality and appropriate documentation when handling sensitive employee matters.
• Ensure established People Operations procedures and policies are followed consistently throughout the contract period.

Qualifications

• 3-5+ years of experience in Human Resources, People Operations, or an HR Generalist role.
• Strong experience supporting employee relations and day-to-day HR matters.
• Working knowledge of federal and state employment laws and HR compliance requirements.
• Experience supporting benefits, employee leaves, offboarding, and employment changes.
• Ability to provide practical HR guidance to employees and managers and appropriately escalate higher-risk matters.
• Strong judgment, discretion, and experience handling confidential employee information.
• Excellent written and verbal communication skills.
• Rippling experience preferred.

Additional information

We at webAI are committed to living out the core values we have put in place as the foundation on which we operate as a team. We seek individuals who exemplify the following:

• Truth - Emphasizing transparency and honesty in every interaction and decision.
• Ownership - Taking full responsibility for one’s actions and decisions, demonstrating commitment to the success of our clients.
• Tenacity - Persisting in the face of challenges and setbacks, continually striving for excellence and improvement.
• Humility - Maintaining a respectful and learning-oriented mindset, acknowledging the strengths and contributions of others.