Chief Executive Officer

Scion Executive Search has been retained to identify the incoming Chief Executive Officer on behalf of our client, Homeschool Boss, a company that provides compliant, high-quality student assessment and testing services for homeschooling families and small schools across the U.S. and internationally. This full-time, hybrid opportunity has headquarters located in Minneapolis, Minnesota.

This is a rare opportunity to lead a high-growth, mission-driven company at an inflection point. With strong fundamentals, a loyal customer base, and significant market tailwinds, the CEO will play a defining role in shaping the future of Homeschool Boss and establishing it as a category leader in a rapidly expanding sector! We’re looking for a mission-aligned leader who is highly organized and systems-oriented - someone who can build structure and scale without disrupting culture and integrity.

ABOUT HOMESCHOOL BOSS:

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. To learn more, visit https://homeschoolboss.com/.

POSITION OVERVIEW:

The Chief Executive Officer (CEO) will lead Homeschool Boss through its next phase of strategic growth, operational maturity, and market expansion. This executive will partner closely with the Founder to maintain daily leadership and establish management systems while building scalable systems, formalizing strategy, and positioning the company to capitalize on rapid market growth.

This is a highly autonomous leadership role requiring both strategic vision and operational discipline. The CEO will oversee business performance, drive expansion through partnerships and new product opportunities, and build the internal infrastructure necessary to sustain their progressive growth trends.

The CEO will inherit a strong product, loyal customer base, and high-growth trajectory, and will be responsible for transforming the organization from founder-led operations into a structured, high-performing enterprise.

KEY RESPONSIBILITIES:

Strategic Leadership & Growth

• 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

Operational Excellence & Scalability

• 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

Financial Leadership & Business Discipline

• 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

Organizational Leadership & Team Development

• 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

Customer Experience & Market Reputation

• 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

Partnerships & External Relations

• Evaluate, structure, and manage strategic partnerships and vendor relationships
• Expand presence in key growth markets (e.g., Texas, Florida)
• Represent the organization with stakeholders, partners, and industry groups
• Navigate relationships involving state programs, compliance requirements, and education ecosystems

Founder Partnership & Governance

• 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

COMPENSATION AND BENEFITS:

In addition to a competitive base salary of $180,000 to $200,000, Homeschool Boss also provides a comprehensive benefits package which includes annual bonus; access to robust health, vision, and dental insurance; 401(k) with employer match, Health Savings Account (HSA); and unlimited PTO.

APPLICATIONS AND NOMINATIONS:

Homeschool Boss has retained the services of Scion Executive Search, a national executive search firm specializing in nonprofit recruitment, to assist in conducting this important search. For immediate consideration, please apply with your resume and cover letter, formatted in Microsoft Word, via: https://scionexecutivesearch.com/job/14481.