Role Description At Carrum, we live and breathe the mission of transforming the healthcare system to create an unmatched experience for patients. If you are passionate about changing healthcare and want to finally get rid of surprise bills, poor quality, and high prices, while thriving in an entrepreneurial, cutting-edge environment, we would love to connect with you. The Chief of Staff (CoS) to the CEO reports to the CEO and will play a critical role in our success. We’ve experienced tremendous growth in the last few years and we’re looking for someone with exceptional leadership talent and the ability to lead by influencing through respect and trust, rather than formal authority. The Chief of Staff is the strategic integrator of our leadership team, serving as the connective tissue between vision and execution. Your mission is to maximize the CEO’s impact and ensure the organization moves as a single, high-velocity unit. Qualifications - 10+ years experience, preferably with prior experience at a growth-stage startup and at a consulting firm. - Deep experience in stakeholder and project management. - Ability to influence without positional authority. - Proven track record of designing executive operating rhythms and repeatable decision-making frameworks. - High-velocity execution partner with organizational diplomacy. - AI Evangelist with the ability to architect a strategic roadmap for AI-driven workflows. Requirements - Expand CEO's Execution Capacity. - Lead High-Stakes Special Projects. - Design the Operating Cadence. - Codify Decision-Making. - Maturity of Metrics. - Drive Organizational Diplomacy. - Own the Goal-Setting Lifecycle. - Hold the Line on Accountability. - Disciplined AI Adoption & Operationalization. - Build Internal AI Capabilities. Benefits - Stock option plan. - Flexible schedules and remote work. - Chicago and San Francisco offices available. - Self-managed vacation days, within reason. - Paid parental leave. - Health, vision, and dental insurance. - 401K retirement plan. Company Description We’re a health tech company that brings value-based care to the masses. We help employers deliver a memorable patient experience, immediately lower healthcare costs, and drive better outcomes through the power of technology and human-centered design. Since launching in 2014, we’ve partnered with Fortune 500 employers and top hospitals across the nation. Carrum Health is an equal opportunity employer and encourages all applicants from every background and life experience.

Role Description Accepting applications for the 2026–2027 school year. Working remotely, the K-8 Dean of Students will work collaboratively with the leadership team. The Dean of Students will work closely with School Support, Enrollment, Technical Support, Materials Management, Fulfillment, Finance, Human Resources, Payroll, and Facilities Management. It is also anticipated that this individual will manage a range of special projects and duties, including all state-mandated protocols for schools in the state. - Collaborate with and support counseling team; - Facilitate communication between teachers, Learning Coaches, and students; - Track and support staff work with school data sets and plan for staff training; - Serve as a member of the leadership team and collaborate on improving student performance, engagement, and schoolwide protocols; - Manage the implementation of the proven Connections Academy operational protocols; - Oversee staff professional development services; - Support school administration in managing the school’s budget and various grants; - Supervise and motivate staff in pursuit of school goals, including oversight of approximately 10 direct reports across K–8 grade bands; - Support student accounting functions including attendance maintenance; - Lead K–8 truancy intervention efforts, including communication with families, tracking interventions, finalizing truancy lists, and supporting Intent to Return (ITR) processes; - Manage reconciliation between Connections Academy’s data systems and state and local student information systems; - Act as the human resources liaison for school staff in the areas of benefits, leave tracking and the maintenance of local files; - Act as the technology liaison for teachers and administrative staff; - Monitor all enrollment requirements and communicate requirements to the Enrollment Department; - Support onboarding and transition processes for new families to ensure successful integration into the school community; - Manage and communicate K–5 and Middle School Huddle IA updates and support schoolwide data monitoring, including benchmark implementation and progress tracking; - Coordinate and oversee afterschool tutoring programs, including staffing, communication, and student participation monitoring; - Coordinate implementation of digital citizenship initiatives and the 7th-grade social media course in alignment with state requirements; - Provide state testing support including logistics for scheduling, tracking participation, and contracting for testing facilities; - Support contracting for supplemental student services; - Monitor and track all school-based assets; - Support the Marketing Department with student outreach, marketing, and public relations; - Plan and coordinate virtual student engagement activities and events, including spirit weeks, guest speakers, assemblies, and other school culture initiatives; - Stay current on the state’s policies, procedures, and legislation; - Be available to handle all emergencies; - All other duties as assigned. Qualifications - Minimum of 5 years of relevant work experience - Master’s degree is preferred - Alabama teacher or counselor certification - Administrative or management experience within a school environment - Excellent communication skills, both oral and written - Demonstrated ability to work well in a fast paced environment - Technologically proficient (especially with Microsoft Office products) - Experience in managing people a plus - Ability to travel as-needed - Please note 2-step authentication is required to set-up to login to all systems if given a job offer. Benefits Benefits available to eligible employees can be seen at Connections Academy Benefits .

• Lead and manage Accela’s enterprise-wide strategic planning process • Establish governance frameworks to ensure alignment and accountability for strategic objectives • Deliver executive-level reporting on progress, including status updates, risk identification, and issue resolution • Ensure strategic objectives are clearly defined, measurable, and achievable • Plan and facilitate quarterly strategic planning sessions with the Senior Leadership Team • Lead high-priority, COO-sponsored initiatives from concept through execution • Translate strategic concepts into detailed, executable operating plans • Monitor progress against plans, identify gaps, and provide regular updates to executive leadership • Partner cross-functionally to assemble and lead initiative teams, driving alignment and outcomes • Support the COO in developing executive briefings for the Executive Leadership Team (ELT), Board of Directors, and other key stakeholders • Ensure communications are clear, concise, and aligned with organizational priorities • Establish and manage governance for Monthly Operational Reviews (MORs) • Define agendas, coordinate participating teams, and ensure readiness of materials • Facilitate review sessions and drive productive discussions • Track, manage, and follow up on action items to ensure accountability and closure

Role Description School Leadership focuses on leading and managing areas of business operations within the school including: - Leading development and implementation of plans, policies, and strategies in support of business objectives - Creating and tracking key performance metrics - Collaborating with internal stakeholders to support initiatives that drive operational and financial performance and growth The Dean of Students works with the school’s Principal and leadership team to cultivate a positive, supportive school culture for all scholars. In this role, you will help lead the school’s efforts to create a positive, structured, achievement-oriented, and joyful school culture. The Dean of Students will report directly to the school Principal and receive coaching from both the Principal and Director of Curriculum and Instruction. The Dean of Students will also coach a portfolio of teachers. This is a full-time remote position. Ability to work independently, typically 40+ hours per week is required. Ability to maintain a professional home office without distraction during workday, typically 9-5 (or 8-4) or as defined by the school. Qualifications - Bachelor’s degree - Five (5) years of experience in education OR equivalent combination of education and related experience - Ability to travel 25% of the time - Ability to pass required background check - Valid IVP fingerprint clearance card Requirements - Build positive relationships with students grounded in respect, enthusiasm, achievement, courage, hard work, and self-determination through structured social-emotional learning - Ensure that behavioral expectations and school culture standards are met - Support teachers in holding all students to consistent, high behavioral expectations for all students - Act as a resource to teachers in their instructional practice, especially as it relates to issues of relationships with students, classroom management, and school culture - Lead staff efforts to ensure all students have excellent attendance and engagement - Develop and maintain communicative relationships with families, emphasizing families’ roles as collaborators and accountability partners for their student’s academic and behavioral performance, including attendance - Communicate regularly with families regarding student performance and academic achievement - Assist with parent and student concerns and issues - Collaborate with the Principal and leadership team to establish a positive, structured, achievement-oriented, and joyful school culture - Participate in regular leadership team meetings at the school level and network level - Help articulate the school’s mission and vision with the aim of ensuring all stakeholders have a common understanding and are positioned to work cooperatively in order to achieve desired results - Utilize/relies heavily upon communication technologies and practices that most effectively support a predominantly virtual/remote work environment - Ensure that the school is meeting the needs of students while complying with local, state, and federal laws regarding special education and other categorical programs Desired Qualifications - Strong written and verbal communication skills - Excellent problem-solving skills - Organizational skills, multi-tasking abilities - Customer service focus - Adaptable and comfortable in a fast-paced work environment - Proficiency in Microsoft Office Suite (Word, Excel, Outlook, PowerPoint); Web proficiency - Familiarity with the online learning experience - Experience working with the proposed age group - Experience supporting adults and children in learning and the use of technology - An ability to learn new technology tools quickly (e.g. database and web-based tools) Benefits - Stride, Inc. considers a person’s education, experience, and qualifications, as well as the position’s work location, expected quality and quantity of work, required travel (if any), external market and internal value when determining a new employee’s salary level. - Salaries will differ based on these factors, the position’s level and expected contribution, and the employee’s benefits elections. - Offers will typically be in the bottom half of the range. Work Environment The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. This is a home-based position.