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