Chief of Staff

Summary

Join TailorCare, a rapidly growing remote-first company, as our Chief of Staff! In this critical role, you will directly support our CEO and executive team, managing the Office of the CEO and driving company-wide initiatives. You will be responsible for project management, optimizing internal processes, and preparing materials for executive and board meetings. The ideal candidate possesses a strong background in project management and healthcare, coupled with exceptional communication and organizational skills. We offer a supportive and inclusive work environment with a comprehensive benefits package, including generous PTO, paid parental leave, and comprehensive health insurance.

Requirements

• 5+ years of overall work experience, preferably 2-4 years of relevant experience working directly with senior executives in healthcare
• Bachelor’s degree required
• Experience driving large complex projects in growth stage or mature corporate environments

Responsibilities

• Work directly with the CEO to ensure execution of operational priorities of the Company and Executive team
• Manage the Office of the CEO in collaboration with the CEO, Executive Assistant, and other members of the Executive team
• Optimize internal processes and communication across departments to increase organizational effectiveness
• Drive project management efforts, overseeing multiple projects from inception to completion while ensuring they meet timelines and objectives
• Manage Executive Team meetings including, but not limited to, setting the agenda, capturing meeting minutes and action items, providing insights and analysis to inform strategic conversations, building meeting materials, and tracking follow through to increase accountability
• Support the CEO and Executive team to develop materials for Board meetings, including setting agendas, coordinating material development and preparation, and liaising with Directors
• Coordination of cross-departmental onsite meetings, including setting agendas, documenting outcomes, and following up on action items to maintain momentum on key projects
• Prepare reports, presentations, and other materials for internal and external stakeholders, synthesizing complex information into clear and actionable insights
• Develop and maintain project timelines, track progress, and provide regular status updates to the Executive team
• Support other departments as needed to drive cross-functional, high value projects across the company
• Take on ad-hoc, high-visibility special projects and initiatives that require cross-departmental coordination

Preferred Qualifications

• MBA or advanced degree in business, management, or a related field
• Healthcare experience, including but not limited to value-based care, digital healthcare, health insurance or care delivery
• Proficient in project management tools and software, as well as Google Suite (Docs, Sheets, Slides)
• Broad-based, decisive program management expertise with strong planning, communication, organizational, and process analysis/improvement abilities to successfully direct and deliver concurrent projects while minimizing risk to stakeholders
• Strong executive-level verbal and written communication skills and excellence developing executive- level presentations
• Detail-oriented strategic thinker with analytical problem-solving capabilities and thrives in ambiguity
• Strong interpersonal skills, with the ability to build relationships at all levels of the organization
• A proactive and solution-oriented mindset, with a focus on driving results and continuous improvement
• Comfort with decision-making in ambiguous situations, and operating in fast-moving environments

Benefits

• Meaningful Work: We are dedicated to our mission and deeply value our patients and each other. Each day offers the opportunity to make a positive impact
• Work Environment: We operate as a remote-first company with options for a hybrid work model in Nashville
• Time Off: Our generous paid time off (PTO) and holiday plans ensure you have ample time to rest and recharge
• Family First: We offer paid parental leave and support a healthy work-life balance, encouraging flexibility and autonomy. We love talking about our family and pets!
• Comprehensive Benefits: From Day 1, employees enjoy medical, dental, vision, life, and disability insurance, wellness resources and an employer HSA contribution
• Fair Compensation: We are committed to equitable pay for all team members and support your future goals with a 401k plan that includes employer matching
• Community: We foster an inclusive environment where you can rely on your teammates, share honest feedback, and feel comfortable being your authentic self at work each day