People Operations Generalist

Job Description

Job Description

Salary :   $75-80k annually

Benefits :   Free employee-only medical coverage under one of our plans. Free short-term disability and FREE life insurance coverage.  Plus, a 4% employer match with our 401(k).  Other incredible benefits HERE.

Location :   Candidates in Chicago, Houston, Austin, or Phoenix will be considered

Your Mission :

Your mission is to ensure the seamless execution of Playbook’s core people operations by managing talent acquisition, payroll administration, and benefits compliance with precision and care. As one part of a two-person People Operations team, you’ll get the opportunity to work within every facet of HR. You’ll serve as the connective force between candidates and Playbook, driving efficiency, clarity, and consistency across every stage of the candidate experience.

The Legacy You'll Leave :

You supported the evolution of a streamlined, high-performing People function that balanced precision with empathy. Through your consistency and attention to detail, you elevated the candidate experience and strengthened trust across teams. Your impact was felt in every hire made, every process improved, and every employee who felt supported through precise, efficient, and people-centered operations.

What You're Responsible For :

• Lead full-cycle talent acquisition. Guide candidates through every stage of the hiring process with care and professionalism, ensuring each new hire reflects our values, strengthens our culture, and supports the company’s growth.
• Own the candidate pipeline. Keep candidate pipelines organized and moving smoothly, maintaining accuracy and communication so every applicant feels valued and informed throughout their journey.
• Champion the candidate experience. Create a thoughtful and engaging experience for every candidate while partnering closely with Hiring Managers, our Executive Assistant, and our Senior Director of People Operations to build strong, connected teams.
• Drive continuous improvement. Use insights and feedback to refine recruiting processes, enhance sourcing strategies, and continually improve the way we attract and welcome top talent into our company.
• Oversee benefits compliance. Partner closely with our insurance broker, Sequoia, to maintain ongoing healthcare compliance, complete quarterly tasks, and keep the Sequoia People Platform up to date. Stay ahead of deadlines by reviewing compliance checklists regularly and collaborating with the account manager for guidance and clarity.
• Administer and prepare payroll. Coordinate biweekly payroll activities for contractors and host teams, ensuring job codes, time approvals, and contractor communications are accurate and complete. Maintain clean, organized systems so every team member is paid correctly and on time.

Who You Are - Baseline Expectations :

Who You Are - Core Competencies :

Our Core Values :

Playbook's culture is based on a shared respect for our lived values HERE.  Fit with our values is a critical component of our hiring process, and you and all of our colleagues are expected to live our core values in interactions with team members, customers, and stakeholders.  An assessment of how you have exhibited our values is also an important part of your performance review process.

Our Commitment To You :

Playbook is committed to building a team that represents a variety of backgrounds, perspectives, and skills.  We know the more inclusive we are, the greater our impact will be!

A Quick Note About Salaries :

We list salaries based on a few key factors.  These include location-specific budgets, market trends, team size, and the scope of the building.  Since we’re a national company working with office properties of all shapes and sizes, the listed salary is tailored specifically to this role and may differ from similar-titled roles on our Careers Page. Curious or want to chat more about it?  We promise to be open and transparent about these details throughout our interview process.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.