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