Executive Support & Project Specialist | Road to Hire

Road to Hire • Charlotte, NC

3d • $30 - $34 • Hybrid

About The Position

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, Technology and Operations (STO) to ensure seamless execution of strategic priorities.
Priority consideration for interviews will be given to applicants who submit by Monday, April 20th, 2026.

Requirements

• 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
• 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
• 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

Nice To Haves

• Experience in a similar industry or corporate environment with exposure to organizational change management
• 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

Responsibilities

• 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
• 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
• 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

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 101-250 employees