Chief Advancement Officer | Road to Hire

Chief Advancement Officer (CAO)

Organization: Road to Hire
Reports To: Chief Executive Officer
Department: Executive Leadership Team + Workforce, Innovation and Alumni Network (WIN)

Location Requirements: This is a hybrid position that requires full-time residence in the Charlotte region with required in-office presence Tuesday through Thursday. In community and beyond presence may occur on remote days depending on meeting schedules. Occasional weekends and evenings may be required.

Target Compensation: $150-$158K depending on experience  + full benefits

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.

To apply or nominate an exceptional candidate: Road to Hire is actively soliciting nominations and direct applications for this executive search. To nominate an exceptional candidate, please email their name, current role, email address, and LinkedIn profile link (if available) with the subject line "Founding Chief Advancement Officer Search" to r2hexecutivesearch@roadtohire.org. To submit your own application for consideration, please email your resume and cover letter with the same subject line to the same address.

Submissions received on or before January 5, 2026 will receive priority consideration and review. Due to the volume of applications, the hiring manager (CEO) nor Road to Hire can accept calls or individual requests for time unless selected for the interview process.

 

Position Summary

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 founding Chief Advancement Officer (CAO) to join our executive leadership team, reporting directly to the Chief Executive Officer. The CAO is a newly created role and a key member of Road to Hire’s new Executive Leadership Team, serving as a critical supporting leader to the CEO. As the CEO builds out the Road to Hire Executive Leadership Team, this position reflects the organization’s new direction and growth strategy for the next decade.

This role requires a strategic, high-capacity executive who can serve as both a trusted partner to the CEO and a strong, independent leader. The CAO will oversee multiple teams at scale while also managing an individual portfolio of high-impact work that generates direct revenue to support the organization’s mission.

The CAO will lead and drive impact across two interconnected, revenue-generating functions and will directly supervise four staff members: three team leaders (Corporate Partnerships; Workforce/Apprenticeships; and Alumni) and one individual contributor (Donor Associate).

Philanthropy and Corporate Engagement – Serve as the organization’s Chief Major Gifts Officer, partnering with the CEO to grow and diversify Road to Hire’s philanthropic and corporate investment portfolio both locally and nationally.

Workforce, Innovation, and Alumni Network – As a member of the Executive Leadership Team, lead multiple front-line teams focused on corporate partnerships, workforce development, and alumni engagement.

Impact of the Role
As both strategist and executor, the founding Chief Advancement Officer will bring immediate executive-level impact, relationships, and acumen that accelerate the Road to Hire mission. By uniting innovation, opportunity, and investment under a shared advancement strategy, this leader will accelerate organizational growth, deepen community impact, and ensure long-term sustainability.

The CAO will play a pivotal role in driving transformative partnerships, expanding resources, and amplifying Road to Hire’s mission to create pathways to lasting economic mobility.

Purpose:
Drive organizational sustainability through diversified philanthropic and corporate investment, serving as both a strategic partner to the CEO and Road to Hire’s lead fundraiser and advancement executive. This aspect of the role requires a seasoned philanthropic leader with experience driving impact, a demonstrated track record of closing major gifts, and excellence in donor stewardship and management. The ideal candidate brings strategic vision paired with hands-on execution, acting as both a thought leader in philanthropic strategy and a working executive who integrates major gift fundraising with strong donor relations.

Road to Hire’s philanthropic strategy is grounded in substantial lead gifts from founding partners and the organization’s founder, complemented by strategic public and private investments. Due to strong demand and demonstrated support from our school district, R2H has entered a strategic growth phase and is actively working to expand and diversify its funding portfolio while preserving its core founding financial foundation.

 

Key Responsibilities

Philanthropic Leadership:
In partnership with the CEO, manage a portfolio of local and national high-net-worth donors, corporate partners, and foundations. Cultivate, solicit, and steward multi-year, six- and seven-figure commitments. Previous experience managing high-net-worth philanthropic relationships with significant confidentiality and discretion is essential. Oversee revenue streams from public and private funding, including identifying and stewarding new funding prospects at both the national and local levels.

CEO Partnership:
Collaborate closely with the CEO to plan and execute donor engagement strategies, board cultivation efforts, and transformational fundraising opportunities.

Strategic Advancement Planning:
Design and implement a comprehensive advancement strategy encompassing individual giving, corporate philanthropy, foundation partnerships, and planned giving.

Corporate Engagement:
Leverage and expand relationships with corporate leaders to drive both philanthropic investment and workforce collaboration.

Grant Strategy and Compliance:
Oversee grant development, contract compliance, and reporting to ensure alignment with program priorities and fiscal accountability across private and public funding streams, in collaboration with the Donor Associate who reports to this role.

Donor Stewardship:
Cultivate a culture of gratitude and excellence in donor communications, ensuring personalized, high-impact engagement experiences for supporters.

 

Workforce, Innovation, and Alumni Network Team

Purpose:
Lead the development and execution of Road to Hire’s workforce programming and team, corporate engagement,  and alumni engagement strategy, ensuring alignment with industry needs and long-term impact for graduates.

Key Responsibilities

Vision and Direction:
Define and communicate a clear vision for the WIN team that aligns with organizational goals and KPI’s. 

Market Alignment:
Continuously monitor labor market trends to ensure programming and strategies remain competitive, responsive, and forward-thinking.

Strategic Oversight:
Lead and empower the Workforce, Innovation, and Alumni Network teams (Workforce Partnerships, Apprenticeships, Alumni) to design and implement innovative, data-driven programs that produce exceptional outcomes.

Program Innovation:
Develop and scale industry-aligned workforce initiatives, pathways, and emerging workforce solutions in alignment with mission, goals and CEO priorities.

Corporate Workforce Partnerships:
Cultivate and expand high-impact partnerships with employers and industry leaders to create hiring pipelines for full-time roles and internships.

Measurement and Impact:
Report and oversee systems to ensure measure of leading and lagging progress and path to goals across all teams. 

 

Organizational and Strategic Leadership

Serve as a strategic advisor and executor to the CEO, translating organizational vision into measurable results across workforce   and philanthropic priorities.

Lead, mentor, and align multi-functional teams across workforce development, alumni relations, and advancement toward shared strategic goals.

Integrate fundraising and workforce strategies into a unified roadmap for mission growth, impact measurement, and financial sustainability.

Collaborate with peers in Marketing, Finance, and Program Operations to ensure consistent messaging, financial stewardship, and operational excellence.

Represent Road to Hire externally with corporate, philanthropic, and community stakeholders as a visible ambassador and thought leader.

 

Qualifications

Education and Experience:

• Bachelor’s degree in Business Administration, Education, Leadership, Public Policy, or a related field; advanced degree strongly preferred.
  
  
• Minimum of 10+ years of senior executive leadership experience in workforce development, philanthropy, or corporate engagement.
  
  
• Proven success leading multiple teams and functions at scale while managing an individual portfolio of high-stakes relationships.
  
  
• Demonstrated success securing six- and seven-figure philanthropic investments at corporate/individual level.
  
  
• Deep expertise in workforce innovation, apprenticeship systems, and social impact partnerships.
  
  
• Experience working closely with CEOs, boards, and senior executives in mission-driven or complex organizations.
  
  

Core Competencies

• Strategic Vision and Execution: Ability to translate bold ideas into measurable, sustainable results.
  
  
• Executive Leadership: Skilled at leading high-performing, cross-functional teams and managing complex initiatives.
  
  
• Relationship Management: Exceptional ability to engage, influence, and inspire diverse stakeholders, from C-suite leaders to community partners.
  
  
• Financial and Data Acumen: Strong analytical and fiscal management skills with an emphasis on accountability and impact measurement. Proficiency with CRM systems and fundraising technology platforms.
  
  

Leadership Qualities

• Strategic thinking with the ability to translate vision into actionable plans.
  
  
• A trusted and collaborative partner to the CEO with the confidence and capacity to lead independently.
  
  
• Visionary, innovative, and solutions-oriented leader who thrives in a dynamic, mission-driven environment.
  
  
• Skilled communicator capable of aligning stakeholders around a shared vision.
  
  
• Entrepreneurial and results-oriented, comfortable operating across both strategy and execution.
  
  
• Authentic advocate for Road to Hire’s mission and the communities it serves.
  
  
• Professional discretion in handling sensitive information, managing confidential donor relationships, and navigating complex organizational dynamics.
  
  
• Demonstrated experience supervising direct reports and leading cross-functional teams.
  
  
• Adaptability and resilience in a fast-paced, mission-driven environment.
  
  
• Deep understanding of workforce and philanthropic trends and best practices.
  
  
• Ability to engage and lead effectively in a multi-generational environment.

 

About Road to Hire:

Road to Hire invests in the untapped potential of 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 at the Red Ventures Corporation, its founding corporate partner. R2H is a standalone 501(c)(3) nonprofit organization.

 

Who We Are:

Red Ventures is a global portfolio of high-growth companies — spanning several U.S. businesses, a joint venture in the health services industry, and strategic investments in Europe. Their businesses include The Points Guy, Lonely Planet, Bankrate, the Allconnect Platform, RV Home Client Growth, RV Growth & Transformation, Sage Home Loans Corporation, and more. Across the portfolio, Red Ventures businesses deliver seamless digital experiences for consumers, help Fortune 100 clients solve large-scale digital growth challenges, and create world-class experiences and opportunities for employees. Learn more at redventures.com and follow @RedVentures on LinkedIn and Instagram.

At Red Ventures, we believe diverse, inclusive teams are better. To help you better understand our core values and beliefs, we encourage you to watch this brief YouTube video: Our Belief Statements. This will give you insight into the principles that guide our work and our commitment to fostering an inclusive environment.

 We offer competitive salaries and a comprehensive benefits program for full-time employees, including medical, dental and vision coverage, paid time off, life insurance, disability coverage, employee assistance program, 401(k) plan and a paid parental leave program.

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 accommodation@redventures.com. 

If you are based in California, we encourage you to read this important information for California residents linked here.