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