Chief of Staff / Dir. Human Resources

Lemonaid Health is a mission driven technology startup committed to providing quality and affordable healthcare to patients nationwide. We build long term relationships with patients by offering a broad range of primary care services to help them lead happier, healthier lives
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

Originally posted on Himalayas