Chief Executive Officer

About the role

Homeschool Boss is a rapidly growing, for-profit education services company serving the expanding school-choice and homeschooling market across all 50 states and internationally. Founded in 2016, the organization provides high-quality, compliant student assessment solutions, supporting over 48,000 students annually and projected to exceed 100,000 in the coming year. With exclusive partnerships, a strong reputation for customer experience, and significant tailwinds from school choice legislation, Homeschool Boss is entering a critical phase of scale. The company provides a mission-driven approach to delivering essential services in a fragmented and underserved market. The organization is fully remote, values work-life balance, and fosters an inclusive, highly collaborative culture with strong representation across diverse and LGBTQ+ communities.

Responsibilities

• Develop and execute a comprehensive, multi-year strategic plan aligned with market opportunities in school choice and homeschooling
• Identify and pursue new revenue streams, partnerships, and product extensions
• Analyze market dynamics (including state-level policy changes) to inform expansion strategy
• Establish measurable growth targets, KPIs, and performance benchmarks
• Position the company to scale from a mid-sized business to a significantly larger enterprise
• Build and implement scalable operational systems to support rapid growth and seasonal demand
• Improve planning, forecasting, and capacity management, particularly for peak testing seasons
• Introduce structured management processes (e.g., one-on-ones, performance systems, workflows, etc.)
• Drive efficiency in customer experience, scheduling, and service delivery
• Ensure operational readiness for projected growth of 40 – 50%+ annually
• Enhance financial planning, budgeting, and resource allocation processes
• Ensure disciplined investment in growth initiatives, partnerships, and infrastructure
• Monitor key financial metrics and ensure long-term sustainability
• Partner with finance leadership to improve forecasting and margin optimization
• Build and lead a high-performing leadership team capable of managing daily operations
• Strengthen management layers and reduce founder dependency
• Develop workforce planning strategies to support seasonal and long-term staffing needs
• Foster a culture of accountability, empowerment, and continuous improvement
• Maintain and protect a highly inclusive, respectful, and mission-driven culture
• Ensure a consistently high-quality experience for families, schools, and partners
• Improve key service metrics (e.g., scheduling speed, satisfaction, repeat customers, support volume)
• Maintain the company’s reputation as a best-in-class provider in a fragmented market
• Evaluate, structure, and manage strategic partnerships and vendor relationships
• Expand presence in key growth markets (e.g., Texas, Florida)
• Navigate relationships involving state programs, compliance requirements, and education ecosystems
• Partner closely with the Founder, who will remain engaged in strategic and market-facing work
• Translate founder vision into executable plans and organizational systems
• Operate with high autonomy while maintaining alignment on major decisions
• Provide clear, data-driven communication and recommendations

Qualifications

• Proven experience as a senior executive scaling an organization (e.g., ~$2M to $10M+ revenue and beyond)
• Experience in B2C, edtech, education services, or similarly complex service-driven industries
• Exposure to nonprofit or mission-driven environments
• Experience navigating rapid growth in emerging or underserved markets
• Experience building new product lines or expanding service offerings
• Demonstrated success in building operational systems and scaling infrastructure
• Strong business and financial acumen, including budgeting and growth planning
• Experience leading organizations of approximately 30 to 100+ employees
• High emotional intelligence and ability to lead diverse teams
• Ability to lead in a remote, distributed workforce environment
• Familiarity with government programs, state-level requirements, or compliance-driven markets preferred
• Strong partnership, communication, and stakeholder management skills