Director, Execution (Remote)

Do you have a passion for children and education? Would you like to positively impact families in need of help? We want to speak with you! Step Up For Students empowers families to pursue and engage in the most appropriate learning options for their children. Step Up For Students empowers families to pursue the most appropriate learning options for their children. We unite communities to provide scholarships that open doors to a stronger future. With this support, students can choose the right learning environment and access resources to reach their full potential. Our culture is rooted in two core values: Everyone is an asset Every event is an improvement opportunity These values guide how we work together and continuously improve. We expect every team member to bring these principles to life in their daily work. The Director, Execution is a strategic leader responsible for advancing CEO-sponsored initiatives and driving enterprise-wide execution of high-impact priorities. This role partners closely with the CEO and Chief of Staff to ensure alignment across the executive agenda and to translate strategic objectives into clear, measurable outcomes. This leader oversees cross-functional coordination, ensuring teams remain aligned, accountable, and on track to achieve organizational goals. The Director is responsible for monitoring and reporting on enterprise OKRs, providing leadership with clear visibility into progress, risks, and results. In addition, the Director leads and executes special initiatives outside of traditional EPMO structures — such as rapid-response “tiger teams”— to address critical business needs with speed and precision. This role is ideal for a highly agile leader who thrives in fast-paced environments, brings structure and clarity to complex initiatives, and consistently delivers results across executive-level priorities. Location: Remote (United States) Key Responsibilities: Drive execution of CEO-sponsored priorities and enterprise-level operational efforts. Align to the CEO and work in tandem with the Chief of Staff to ensure alignment and avoid duplication across internal workflows. Develop and manage OKRs across departments, ensuring visibility, accountability, and progress tracking. Lead cross-functional coordination and delivery of operational workstreams, especially those outside formal EPMO scope. Build lightweight execution frameworks to support scalable delivery and stakeholder alignment. Monitor and report on progress using dashboards, KPIs, and executive-level updates. Identify risks and resource gaps; develop mitigation strategies to ensure successful outcomes. Support enterprise change efforts, including communication planning and stakeholder engagement. Prepare executive-level materials to support strategic decision-making and board-level reporting. Travel up to 30% to support initiative delivery and stakeholder engagement. Qualifications: Demonstrated success and a proven track record in professional/life experience in specific job functions, projects, or industries. Military service can substitute for professional experience and/or formal education requirements. 10–15 years of progressive leadership experience in operations, program execution, or enterprise delivery operating at the C-suite level. Proven success leading cross-functional workstreams in complex or matrixed environments. Experience in sectors such as education, financial services, not-for-profit, or related industries. Strong digital fluency and proficiency with Microsoft Office Suite and collaboration tools. Exceptional communication, stakeholder engagement, and organizational skills. You’ll Stand Out If You Have: Experience in organizations undergoing rapid growth or transformation. Background in both startup and enterprise settings. Familiarity with governance, compliance, and operational frameworks. Key Competencies: Demonstrates critical Transformation and Leadership skills and abilities: True Collaboration; Focusing on Outcomes: Owning and effectively solving problems for today and the future; Empathetic Leadership; Adaptability and Resilience; Emotional Intelligence/CEM skills and Continuous Development/Continuous Improvement Mindsets Strong interpersonal skills with the ability to engage diverse stakeholders including board members, executives, and partners. High digital fluency and comfort with productivity and collaboration tools. Strong emotional intelligence and ability to navigate complex decision-making. Strategic thinking paired with disciplined execution. Excellent verbal and written communication skills. Strong analytical and problem-solving capabilities. Ability to manage multiple priorities in a fast-paced environment. High attention to detail, discretion, and sound judgment. Interview Process: Veriff Identity Verification Recruiter Video Interview Hiring Manager Video Interview Senior Leadership Team Member Video Interview Chief Executive Officer Video Interview Why you’ll love working here: Award-Winning Culture: We’ve been named one of the Best Companies to Work For four years in a row by Florida Trend and Workforce Research Group and honored as one of the Healthiest Companies by Florida’s First Coast Worksite Wellness Council. Fast Company recognized us as one of the Best Workplaces for Innovators—proof that we foster an environment where big ideas and bold thinking are encouraged. Comprehensive Benefits: Enjoy medical, dental, and vision coverage, plus HSA, FSA, and Lifestyle Spending Accounts. We also offer a competitive 401(k) with company match to help you plan for the future. Flexibility & Work-Life Harmony: Remote work options and unique time-off programs—including 14 paid holidays, Care and Parental Leave, and our Flexible Leave policy. Growth & Development: From mentorship programs to management training and professional development opportunities, we invest in your career journey every step of the way. Supportive Professional Environment: Our dedicated coaching team is here to help you succeed, and employee-led committees give you a voice in shaping our workplace. Collaboration isn’t just encouraged, it’s how we work. Working Conditions and Equipment Use: Work is performed indoors in a typical office environment - not substantially exposed to adverse environmental conditions. Valid driver’s license and proof of insurance may be required, depending on role responsibilities. Must be able to lift up to fifteen (15) pounds. Frequent use of office machines to include telephone, computer, and printer. Step Up For Students is an equal opportunity employer committed to diversity & inclusion in the workplace. Apply To This Job