Chief of Staff

Chief of Staff About the Company High-growth digital marketplace Industry Retail Type Privately Held About the Role The Company is seeking a Chief of Staff or Chief Operating Officer to work closely with the CEO and Senior Leadership Team. This pivotal role is focused on amplifying the CEO and SLT by optimizing time, decision-making, and execution. The successful candidate will be a trusted partner, gatekeeper, and execution lead, particularly in the areas of strategy and action. A background in digital and eCommerce, advertising, and marketing operations is essential, with a preference for those who are AI-native and tech-savvy. The role involves translating the CEO and Board's vision into actionable plans, driving cross-functional initiatives, and preparing the CEO for various engagements. The ideal candidate will have a strong understanding of D2C customer acquisition, eCommerce, and performance advertising, as well as experience in scaling fast-growing companies. Applicants for this role at the company should have a proven track record of supporting CEOs or Founders in fast-scaling SMBs, with a minimum of 7-12 years' experience. Board-level confidence, the ability to lead high-impact special projects, and a proactive approach to problem-solving are also key requirements. The role demands a candidate who can run executive and SLT meetings, track priorities, and metrics, and ensure clear communication and follow-through. A passion for eLearning, online training, and the company's focus areas such as health, wellness, and fitness, is a plus. The Chief of Staff/COO will be responsible for a wide range of tasks, including drafting CEO communications, coordinating board and investor materials, and resolving cross-functional blockers. The position is fully remote and requires a candidate who is based in the USA or Canada. Hiring Manager Title Chief Executive Officer (CEO) Travel Percent Less than 10% Functions General Management Strategy Operations