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 philanthropi