Chief Advancement Officer | Road to Hire

Red Ventures-posted about 8 hours ago
$150 - $158/Yr
Full-time • Executive
Hybrid • Charlotte, NC
1,001-5,000 employees
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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.

  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
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