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