People Operations Manager

Letter AIChicago, IL
Hybrid

About The Position

We’re hiring our first People Operations Manager, a hands-on, strategic builder who will establish and scale the People function from the ground up. This role will own all aspects of People Operations while partnering closely with leadership to support a growing organization (~40 employees and growing). You’ll work within Rippling (HRIS) and play a foundational role in building policies, systems, and culture. This role reports directly to the Founder & CEO of the organization. This is an ideal opportunity for a true HR generalist who thrives in fast-paced environments, takes initiative, and is excited to shape employee experience from day one.

Requirements

  • 5–7 years of experience across Human Resources/People Operations
  • Strong generalist background across multiple HR functions
  • Experience in a high-growth startup or fast-paced, ambiguous environment
  • Comfortable building from scratch with limited infrastructure
  • Self-starter with a bias toward action and ownership

Responsibilities

  • Serve as a trusted advisor to employees and managers
  • Address employee concerns, conduct investigations, and resolve workplace issues
  • Ensure compliance with employment laws and company policies
  • Build and maintain HR policies, procedures, and employee handbook
  • Design and implement learning & development programs and career pathing
  • Support managers with coaching, feedback, and team growth
  • Drive initiatives that strengthen culture and employee engagement
  • Build and manage performance review processes (goal setting, feedback cycles, evaluations)
  • Partner with leadership on performance standards and KPIs
  • Coach managers on performance conversations and improvement plans
  • Oversee payroll in partnership with external providers
  • Administer benefits programs (health, retirement, 401(k), etc.)
  • Ensure compliance with payroll, tax, and benefits regulations
  • Partner with hiring managers on headcount planning and hiring strategies
  • Manage external recruiting partnership and LinkedIn postings
  • Build and elevate employer brand and candidate experience
  • Lead planning of company events (offsites, celebrations, team experiences)
  • Coordinate internal events and engagement initiatives
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