Executive Support & Project Specialist | Road to Hire

Position Overview Road to Hire is seeking exceptional mission-aligned talent to join its team, as it pivots to a new chapter to position itself for new heights of success and organizational excellence. We are seeking a detailed, high-performing and mission-oriented team member to serve as Executive Support Specialist - a unique hybrid role that combines comprehensive executive administrative support with strategic project assistance. This position serves as both the primary executive assistant to our CEO and as the designated project assistant for CEO-driven initiatives that span multiple departments and teams. The role requires exceptional communication skills, the highest level of discretion and confidentiality, and the ability to seamlessly transition between detailed administrative tasks and high-level strategic project support in a fast-paced environment. The Executive Support and Project Specialist will act as an extension of the CEO's office, serving as both trusted liaison and facilitator while simultaneously assisting with organizational initiatives that require cross-functional coordination. This role works primarily with the Office of CEO, with collaboration with R2H’s COO and members of the Office of Strategy, Talent and Operations (STO) to ensure seamless execution of strategic priorities. Key Responsibilities Strategic Project Leadership & CEO Initiative Management Serve as project assistant for designated CEO initiatives, providing comprehensive support and coordination for cross-departmental strategic projects (major projects include events, organizational retreats, strategic planning sessions, and cross-functional initiatives); likely in partnership with the Office of Strategy, Talent and Operations (STO)/COO Assist with project execution from conception through completion, working directly with team members and external stakeholders as assigned by the CEO Support complex project timelines and deliverables across multiple teams, ensuring alignment with organizational priorities and CEO directives Assist with cross-functional collaboration by coordinating team activities, managing stakeholder communications, and helping remove barriers to project success Provide strategic project support, including research, analysis, and recommendations to inform CEO's decision-making on organizational initiatives as requested Assist in monitoring project progress and proactively escalate issues, ensuring accountability and timely completion of all CEO-assigned initiatives Coordinate comprehensive event planning and execution for company-wide events, leadership retreats, and strategic planning sessions in collaboration with the STO/COO Strategic Executive Assistance Serve as the CEO's primary administrative partner, maintaining executive office operations and ensuring seamless daily workflow management Manage sophisticated calendar coordination, including complex scheduling, meeting preparation, appointment management, and comprehensive travel arrangements for the CEO as needed Coordinate strategic meeting preparation by working with the CEO, COO, and leadership team to develop materials for board meetings, leadership sessions, and strategic planning events Handle all confidential correspondence and communications with absolute discretion, serving as a trusted custodian of sensitive organizational information Process executive-level financial tasks, including expense reports, invoices, and budget-related administrative responsibilities for the CEO Maintain organized systems for filing, document management, and information protocols with strict confidentiality measures Serve as primary liaison between CEO and internal/external stakeholders for all scheduling and calendar management needs Proactively manage executive communications, including email screening, prioritization, response drafting, and follow-up coordination Screen and prioritize stakeholder interactions, including incoming calls, emails, and meeting requests, to optimize the CEO's time and focus Facilitate organizational communication flow between the CEO and various departments as needed or requested Operational Support & Coordination Coordinate with support teams, including IT, facilities, and vendors, to ensure seamless office operations Manage office resources, including supplies, equipment, and vendor relationships that support executive functions Maintain organizational systems that support both administrative excellence and project management effectiveness Required Qualifications Education & Experience Bachelor's degree preferred or equivalent combination of education and experience 3-5 years of executive-level administrative support experience with demonstrated progression of responsibilities Experience supporting C-suite executives or senior leadership with a proven track record of managing confidential information Project coordination or management experience with demonstrated ability to lead cross-functional initiatives Strong collaboration and organizational skills with experience working across multiple departments and stakeholder groups Exceptional professionalism, written and verbal communication skills, with the ability to interface professionally with C-level executives, staff, and external stakeholders Technical Skills Advanced proficiency in Microsoft Outlook for comprehensive email management and communication coordination Experience with Canva for creating professional presentations and marketing materials Openness and adaptability to AI tools and emerging technologies Advanced proficiency in Microsoft Office Suite (Word, Excel, PowerPoint) Experience with calendar management systems and travel booking platforms Familiarity with project management tools and document sharing platforms Strong database management and research capabilities Core Competencies Executive presence and strategic thinking with the ability to represent the CEO and the organization professionally Project leadership capabilities with proven ability to drive initiatives from conception to completion Exceptional organizational and time management abilities with skill in managing multiple competing priorities Uncompromising commitment to confidentiality and discretion in all matters, particularly regarding sensitive organizational information Advanced communication and stakeholder management skills, including email management and communication prioritization Strong attention to detail and accuracy, with the ability to maintain high standards under pressure Proactive problem-solving mindset with the ability to anticipate needs and identify solutions independently Professional demeanor and executive presence suitable for high-level stakeholder interactions, with the ability to pivot communication style among diverse audiences (board members, executives, staff, students, external partners) Positive workplace presence with the ability to maintain professionalism while bringing energy and enjoyment to the work environment Deep appreciation and reverence for R2H's mission and unwavering alignment with our commitment to access and opportunity for underrepresented populations Preferred Qualifications Experience in a similar industry or corporate environment with exposure to organizational change management Experience with agentic AI tools, including the ability to build, deploy, and manage AI agents and workflow automations in support of executive and operational functions Project management certification or formal training Experience with board governance and meeting coordination Experience supporting senior executives/C-Suite Experience serving diverse populations Background in supporting organizational transformation or strategic planning processes Compensation Compensation Range: $29.80 - $33.65 per hour *Note actual compensation is based on qualifications, and experience. Additionally, the following benefits are provided by Red Ventures, subject to eligibility requirements. Health Insurance Coverage (medical, dental, and vision) Life Insurance Short and Long-Term Disability Insurance Flexible Spending Accounts Holiday Pay 401(k) with match Employee Assistance Program Paid Parental Bonding Benefit Program Flexible Paid Time Off (PTO): We believe time to rest and recharge is essential. That’s why we offer a generous and flexible PTO policy. Full-time employees accrue 20 days of PTO for a full calendar year annually, with an increase to 25 days after five years of service. About Road to Hire: Road to Hire invests in the untapped potential of underrepresented young adults by breaking down barriers to career success. We provide continuous support from high school classrooms, through college into high-paying careers, and equip young professionals with the skills, confidence, and opportunities to unlock economic mobility and lasting career growth. Road to Hire is headquartered alongside Red Ventures corporation, its founding corporate partner. R2H is considered RV Corporate's social impact vertical while maintaining its status as a standalone 501(c)(3) nonprofit organization. Reports to: Chief Executive Officer Location Requirements: This position requires residence in Charlotte, NC with in-office presence Tuesday through Thursday. Remote work is available Monday and Friday unless special requirements are requested by the CEO. Willingness to align work hours with CEO schedule is essential. Occasional weekends and evenings may be required to support the CEO or R2H events/initiatives. Red Ventures is an equal opportunity employer that does not discriminate against any employee or applicant because of race, creed, color, religion, gender, sexual orientation, gender identity/expression, national origin, disability, age, genetic information, veteran status, marital status, pregnancy or any other basis protected by law. Employment at Red Ventures is based solely on a person's merit and qualifications. We are committed to providing equal employment opportunities to qualified individuals with disabilities. This includes providing reasonable accommodation where appropriate. Should you require a reasonable accommodation to apply or participate in the job application or interview process, please contact [email protected] . If you are based in California, we encourage you to read this important information for California residents linked here . At Red Ventures, we believe in real human connection. That’s why we do not hire someone through text, social media, or email only. As part of the hiring process, you should expect live conversations with RV teammates before any offer is made. Also, keep an eye on the sender: we only use official @redventures.com email addresses at the portfolio level or business specific email addresses (e.g., @thepointsguy.com), not ones like “redventurescareer.com.” We will never ask candidates to send money, buy equipment, or share financial account info during your journey with us. You can always find our open roles on redventures.com— if you receive a message that seems suspicious, please use redventures.com to verify the opportunity. For more, the U.S. Federal Trade Commission has published helpful articles to help individuals learn more about protecting themselves from recruiter scams. If you think you’ve been targeted, feel free to report it to your local authorities. Stay safe out there!