• Act as a trusted strategic partner to the VP by anticipating needs, prioritizing effectively, and enabling strong decision-making in a dynamic environment. • Drive calendar and time management with sound judgment, ensuring focus on the highest-impact work while adapting quickly to changing business priorities. • Orchestrate seamless meetings and events, managing logistics, materials, and follow‑ups so leaders and teams can collaborate at their best. • Support team effectiveness by tracking action items, maintaining organizational resources, and strengthening communication across the Servicing Technology & Product organization. • Lead onboarding and offboarding experiences that help employees and contractors feel welcomed, supported, and set up for success from day one. • Enable productivity by coordinating technology support, equipment, space planning, and supply needs in partnership with internal teams. • Manage special projects and team-wide programs such as offsites, engagement activities, or philanthropic initiatives that strengthen culture and connection. • Draft, edit, and finalize clear, professional communications and presentations that reflect the voice and priorities of senior leadership. • Handle sensitive information with discretion and integrity, modeling trust, accountability, and calm under pressure.

We are looking for an experienced and thoughtful Executive Assistant who thrives in fast-moving, purpose-driven environments. In this role, you will partner closely with the Vice President of Servicing Technology & Product, helping leaders stay focused, connected, and ready for what’s next. You will bring clarity to complexity, confidence to change, and care to every interaction—playing a vital role in how our team delivers meaningful impact at scale. Responsibilities - Act as a trusted strategic partner to the VP by anticipating needs, prioritizing effectively, and enabling strong decision-making in a dynamic environment. - Drive calendar and time management with sound judgment, ensuring focus on the highest-impact work while adapting quickly to changing business priorities. - Orchestrate seamless meetings and events, managing logistics, materials, and follow‑ups so leaders and teams can collaborate at their best. - Support team effectiveness by tracking action items, maintaining organizational resources, and strengthening communication across the Servicing Technology & Product organization. - Lead onboarding and offboarding experiences that help employees and contractors feel welcomed, supported, and set up for success from day one. - Enable productivity by coordinating technology support, equipment, space planning, and supply needs in partnership with internal teams. - Manage special projects and team-wide programs such as offsites, engagement activities, or philanthropic initiatives that strengthen culture and connection. - Draft, edit, and finalize clear, professional communications and presentations that reflect the voice and priorities of senior leadership. - Handle sensitive information with discretion and integrity, modeling trust, accountability, and calm under pressure. Qualifications Required Qualifications - Minimum of 10 years of progressively responsible administrative or executive support experience, including direct support of senior leaders. - Demonstrated ability to work independently, manage competing priorities, and adapt quickly in a fast-paced environment. - Strong judgment and problem-solving skills, with the ability to anticipate needs and think several steps ahead. - Advanced proficiency in Microsoft Word, Excel, PowerPoint, and Outlook, including complex calendar management. - Excellent written and verbal communication skills, with a professional and approachable style. - Proven experience supporting a virtual or hybrid workforce and using audio, video, and collaboration tools effectively. Preferred Qualifications - Experience supporting executives within large, complex organizations, including Fortune 500 environments. - Bachelor’s degree or equivalent professional experience (degree preferred, not required). - Experience coordinating travel, expenses, and multi-location meetings using corporate tools and systems. - High attention to detail paired with the ability to see the bigger picture and align work to business outcomes. - A growth mindset, positive energy, and a collaborative approach that builds strong relationships across teams. If you will be working at home occasionally or permanently, the internet connection must be obtained through a cable broadband or fiber optic internet service provider with speeds of at least 10Mbps download/5Mbps upload. For this position, we anticipate offering an hourly rate of 33 - 49 USD / hourly, depending on relevant factors, including experience and geographic location. This role is also anticipated to be eligible to participate in an annual bonus plan. At The Cigna Group, you’ll enjoy a comprehensive range of benefits, with a focus on supporting your whole health. Starting on day one of your employment, you’ll be offered several health-related benefits including medical, vision, dental, and well-being and behavioral health programs. We also offer 401(k), company paid life insurance, tuition reimbursement, a minimum of 18 days of paid time off per year and paid holidays. For more details on our employee benefits programs, click here. About The Cigna Group Doing something meaningful starts with a simple decision, a commitment to changing lives. At The Cigna Group, we’re dedicated to improving the health and vitality of those we serve. Through our divisions Cigna Healthcare and Evernorth Health Services, we are committed to enhancing the lives of our clients, customers and patients. Join us in driving growth and improving lives. Qualified applicants will be considered without regard to race, color, age, disability, sex, childbirth (including pregnancy) or related medical conditions including but not limited to lactation, sexual orientation, gender identity or expression, veteran or military status, religion, national origin, ancestry, marital or familial status, genetic information, status with regard to public assistance, citizenship status or any other characteristic protected by applicable equal employment opportunity laws. If you require reasonable accommodation in completing the online application process, please email: SeeYourself@cigna.com for support. Do not email SeeYourself@cigna.com for an update on your application or to provide your resume as you will not receive a response. The Cigna Group has a tobacco-free policy and reserves the right not to hire tobacco/nicotine users in states where that is legally permissible. Candidates in such states who use tobacco/nicotine will not be considered for employment unless they enter a qualifying smoking cessation program prior to the start of their employment. These states include: Alabama, Alaska, Arizona, Arkansas, Delaware, Florida, Georgia, Hawaii, Idaho, Iowa, Kansas, Maryland, Massachusetts, Michigan, Nebraska, Ohio, Pennsylvania, Texas, Utah, Vermont, and Washington State. Qualified applicants with criminal histories will be considered for employment in a manner consistent with all federal, state and local ordinances.

• Provide end-to-end executive administrative support for the CMO, including complex and dynamic calendar management, prioritization, and proactive identification of conflicts or adjustments needed • Provide calendar, travel, and expense management support to a few members of the marketing leadership team • Prepare executives for each day by reviewing calendars in advance, confirming attendance, and ensuring meetings are necessary and appropriately resourced • Manage internal and external communications with professionalism, confidentiality, and exceptional attention to detail • Own all aspects of domestic and international travel, including itinerary creation, bookings, logistics, reservations, and contingency planning • Coordinate multi-day offsites, leadership meetings, dinners, and events, ensuring flawless execution from planning through post-event follow-up • Manage all travel and corporate card expenses with accuracy and timeliness—submitting reports within one week of trip completion • Oversee purchase order creation, tracking, and reconciliation, ensuring accuracy across vendors and budgets • Manage the Marketing department’s group credit card, including proactive monitoring, documentation, and issue resolution • Partner with Finance and Procurement to maintain alignment on budget management, accruals, and monthly close needs • Serve as a central coordination point for the Marketing Leadership Team—supporting agendas, materials, meeting logistics, presenters, and follow-ups • Lead administrative planning for recurring events such as Town Halls, ensuring agendas, recognition moments, and presentations are thoughtfully curated and well organized • Build strong cross-functional relationships with other EAs, the broader Marketing organization, and cross-company partners • Maintain exceptional responsiveness via Teams, email, and mobile—particularly for real-time changes and urgent needs • Communicate clearly, directly, and with warmth—reflecting the values and culture of the company • Proactively notify of OOO time, schedule adjustments, and availability changes to maintain transparency and continuity.

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 offers an excellent benefits package: SUFS Total Rewards Medical - HSA/FSA - Dental - Vision Company Paid Disability - Life Insurance 401K Match - Tuition Reimbursement Generous Time off Policy - Professional Development 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. Job Summary: The Executive Assistant to the Chief Executive Officer (CEO) role is a highly visible position at Step Up For Students (SUFS), requiring interaction with a broad range of internal and external stakeholders and playing a key role in support of our mission. The Executive Assistant provides high-level administrative support to the CEO, using discretion, judgment, and knowledge of the organization to facilitate the executive’s activities and maintain confidentiality. This multifaceted role involves complex calendar management across multiple time zones and priorities, coordinating meetings and appointments, preparing materials for presentations and events, and serving as a key point of contact for inquiries and requests. The Executive Assistant assists with and/or manages special projects, conducts research, and performs other tasks assigned by the CEO, thereby contributing to the overall efficiency and effectiveness of the executive office. Location: Remote (United States) Key Responsibilities: - Work directly with the CEO to support all aspects of her daily work routine. - Maintain the CEO’s calendar, including scheduling meetings, appointments, speaking engagements, and travel (may include domestic and international) arrangements. Exercise discretion in committing time and evaluating needs. - Serve as a liaison between the CEO, Senior Leadership, staff, and the public. This includes receiving and screening the CEO’s phone calls and visitors, answering a variety of questions with tact and diplomacy, taking messages, and directing calls appropriately for resolution. - Coordinate work with other Senior Leaders and staff as needed; play a key role in the coordination of staff efforts both within and outside the executive department. - Provide coordination, monitoring, and communication of projects and programs. - Assist, design and or develop and implement activities and processes including project planning, intake, prioritization, initiation, execution, and training, and foster collaboration of end-users and key stakeholders. - Serve as a primary point of contact between the Office of the CEO and governance groups, including helping to coordinate workflow and providing administrative support for governance meetings. - Design and develop presentations for internal and external audiences on behalf of the CEO. - Determine priority of matters of attention for the CEO; redirect matters to staff to handle, or handle matters personally, as appropriate. - Keep the CEO advised of time-sensitive and priority issues, ensuring appropriate follow-up. - Routinely perform a wide variety of support duties. - Compose and prepare letters relating to routine correspondence for the CEO’s signature. - Assist in the preparation and distribution of meeting agendas and materials. - Prepare documents, reports, tables, and charts; distribute as appropriate. - Prepare, reconcile, and submit expense reports. - Maintain confidential and sensitive information. - Attend meetings and take notes of discussion; prepare initial draft of meeting minutes and summaries. - Complete a variety of special projects including creating PowerPoint presentations, financial spreadsheets, special reports, and agenda material. - Participates in professional development and networking conferences and events to maintain and enhance knowledge and competencies. - Other additional and/or alternative duties as assigned from time to time, including supporting other departments or Executives as needed. 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 such as a Bachelor’s degree or higher education in Business Administration, Management, or a related field or equivalent work experience. - 5-7 years of executive support experience, including supporting C-suite executives. - Expert proficiency with Microsoft Office Suite (Word, Excel, PowerPoint). - High degree of professionalism in interacting with diverse groups of stakeholders, including board members, senior executives, staff, community leaders, and donors. - Excellent verbal and written communication skills. - Strong analytical and problem-solving skills. - Commitment to the mission and values of Step Up For Students. You’ll Stand Out If You Have: - Experience supporting a mission-driven, fast-paced executive office, ideally within nonprofit, education, public policy, or highly regulated environments. - Proactive, anticipatory working style, with a demonstrated ability to see around corners and identify needs before the CEO asks. - Exceptional judgment and discretion, with a proven track record of handling sensitive and confidential matters at the highest levels. - Strong executive presence and communication skills, able to draft polished correspondence, represent the CEO professionally, and interact confidently with senior leaders, governance groups, and external partners. - Advanced organizational mastery, including managing complex, multi-time-zone calendars, shifting priorities, and simultaneous high-stakes deliverables. - High proficiency with executive-level presentation development, including building decks, briefing materials, talking points, and event preparation for both internal and external audiences. - Demonstrated ability to manage special projects end-to-end, balancing strategic thinking with hands-on execution. - Calm, steady decision-making under pressure, with the ability to adapt quickly, triage competing priorities, and maintain professionalism in dynamic situations. - Strong stakeholder relationship skills, with the ability to foster trust, influence without authority, and drive alignment across departments. Key Competencies: - Exceptional organizational skills and impeccable attention to detail. - Strong Cognitive Emotional Management (CEM) skills. - Ability to complete a high volume of tasks and projects with little or no guidance. - Ability to react with appropriate levels of urgency to situations and events that require quick response or turnaround. - Professional and polished. - Ability to prioritize tasks effectively. - Proactive and independent with the ability to take initiative. - Excellent time management skills with a proven ability to meet deadlines. - Committed to upholding the highest standards of confidentiality. Interview Process: - Veriff Identity Verification - Recruiter Video Interview - Director of Human Resources Video Interview - Panel Video Interview - Assessment - Final Video Interview with Chief Executive Officer 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 license with proof of insurance. - 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.