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