Chief of Staff / Dir. Human Resources

Lemonaid Health

$120K — $150K *
US-AnywhereRemote in Los Angeles, CA
Healthcare
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 7-12+ years in operations, HR, or senior administrative roles
  • Experience working directly with executives or founders
  • Strong judgment and discretion
  • Excellent written and verbal communication skills
  • Highly organized and calm under pressure
  • Self-directed with a proactive approach
  • Experience in fast-growth or startup environments preferred

Responsibilities

  • Act as a right-hand partner to the President, prioritizing time and decisions
  • Own execution and accountability on cross-functional priorities
  • Prepare briefings and decision memos
  • Ensure meeting outcomes are documented and executed
  • Anticipate issues and propose solutions proactively
  • Coordinate across leadership, vendors, and partners
  • Manage HR operations including hiring, compliance, and employee relations
  • Support organizational design and headcount planning
  • Oversee day-to-day operations and manage vendor contracts
  • Create and maintain internal processes and documentation

Benefits

  • Comprehensive employee benefits including health and wellness programs
  • Opportunities for professional development and career growth
  • Dynamic work environment in a fast-paced culture
  • Direct involvement in strategic decision-making processes
  • Strong support for employee engagement and organizational culture
Full Job Description
Role Overview

We are seeking a Chief of Staff & Head of People to serve as a trusted partner to the President and leadership team. This role is designed for someone who operates at a high level of judgment, discretion, and ownership-not just execution.

This person will extend the President's effectiveness across operations, people, and priority initiatives, while also owning day-to-day administrative, HR, and organizational execution. The role blends strategic leverage with hands-on responsibility and is critical to how the company runs. This is not a traditional assistant role. It is a business operator role with administrative authority.

Responsibilities Overview:

  • Act as a right-hand partner to the President, helping prioritize time, decisions, and initiatives
  • Own follow-ups, execution, and accountability on cross-functional priorities
  • Prepare briefings, summaries, and decision memos
  • Sit in on key meetings and ensure outcomes are documented and executed
  • Anticipate issues before they surface and proactively propose solutions
  • Serve as a point of coordination across leadership, vendors, and partners


People & HR Leadership

  • Own HR operations end-to-end, including:
    • Hiring coordination and onboarding
    • Employee records, policies, and compliance
    • Benefits administration and payroll coordination
    • Performance review processes and employee relations
  • Act as a trusted first point of contact for employees on people-related matters
  • Partner with leadership on organizational design, role clarity, and headcount planning
  • Ensure compliance with employment laws and company policies
  • Support culture, communication, and internal alignment


Operations & Business Management

  • Oversee day-to-day internal operations to ensure the company runs smoothly
  • Manage vendors, contracts, and administrative systems
  • Create and maintain internal processes, documentation, and SOPs
  • Own internal calendars, scheduling, and coordination at the company level
  • Support finance operations (expenses, approvals, light reporting, coordination with accounting)


Operations and Business Management

  • Manage the President's calendar, travel, communications, and logistics
  • Filter and prioritize inbound requests and information
  • Handle sensitive and confidential matters with discretion
  • Act as a proxy for the President when appropriate


What Success Looks Like

  • The President's time is focused on the highest-impact work
  • The organization runs smoothly without bottlenecks or dropped balls
  • Employees feel supported, informed, and aligned
  • HR and operations are proactive, not reactive
  • Leadership initiatives move forward without constant follow-up


Ideal Profile

  • 7-12+ years in operations, HR, chief of staff, or senior administrative roles
  • Experience working directly with founders or executives
  • Strong judgment, discretion, and executive presence
  • Comfortable switching between strategic thinking and hands-on execution
  • Excellent written and verbal communication
  • Highly organized, calm under pressure, and self-directed
  • Experience in fast-growth or entrepreneurial environments strongly preferred

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