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At Williamsburg Learning (WL), we aim to prepare promising students for meaningful lives as principled leaders. We partner with schools like Williamsburg Academy, Leadership Academy of Utah, and Williamsburg Academy of Colorado to deliver transformational learning experiences that spark curiosity, growth, and purpose.
We live by our values—Growth, Right Action, and a Culture of Belonging. We believe work should be meaningful and fun. Our team is authentic, connected, and committed to doing the right thing for each other and the students we serve.
To support our people, WL offers 100% paid health premiums for full-time employees (75% for families), a 100% 401(k) match up to 4%, PTO, plus many more perks!
If our mission and culture resonate with you, we would love to have you on our team!
Position Summary
The Chief Academic Officer (CAO) oversees the critical operations and functions that support the student experience at Williamsburg schools. This includes online academics, local in‑person adventures, curriculum, compliance, and accreditation. This role is a member of the Williamsburg Learning Executive Team and reports to the COO. Essential Duties (Top 5 Roles
The CAO will ultimately be responsible for each of the areas below, but will have assistance to help manage some of these areas: 1) Academic Experience
Enhance the quality, efficiency, and effectiveness of teaching and learning. Implement strategies to enhance student engagement, outcomes, and transformational learning experiences. Establish partnerships within the industry to enhance academic programs and support student success. 2) Programs & Faculty
Scale the academic program to serve all WL markets and partner schools. Direct the strategy and standards for recruiting, developing, and retaining excellent faculty and staff. Drive innovation in educational practices. Lead, manage, and hold accountable (LMA) the Director of Academic Programs. Communicate the vision of the curriculum to meet current and future educational needs. Foster collaboration with the Director of Academic Programs, Program Leaders, and the Director of Curriculum to enhance the existing curriculum and deliver a best‑in‑industry student experience. Drive innovation in curriculum design and technology adoption. LMA the Director of Curriculum. 4) Compliance & Policies
Ensure operational compliance of the Academics Department with Accreditors, partner charter school boards, Education ReInvisioned BOCES, and state and federal regulations. Strategize and direct the accreditation process at WL and its partner schools. Coordinate with school leaders on site visits, state reviews, and board inquiries to ensure effective communication and collaboration. 5) Oversee Williamsburg Adventures
Scale the adventures program to serve all WL markets and partner schools. Develop strategies and standards for quality adventures that foster local community and transformational learning experiences. Operate WAD as an autonomous business unit. LMA the Director of Williamsburg Adventures. Please note that this job description is not designed to cover or contain a comprehensive listing of the activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time, with or without notice. Minimum Qualifications
Senior Academic Leadership:
7+ years in K–12 academic leadership (e.g., CAO, CSO, VP Academics, Head of Schools, Director-level), including managing director‑level leaders. Online School Experience:
Led academics for an online or hybrid K–12 school/program serving
1,000+ students
(preferably multi‑state). Compliance & Accreditation:
Direct experience with K–12 compliance and accreditation (state reporting, audits, site visits; multi‑state exposure strongly preferred). Technology & AI:
Comfortable using data and educational technology to drive decisions, with
hands‑on experience implementing AI or emerging tools
in a human‑centered way. Mission Alignment:
Clear alignment with
classical / liberal arts / leadership‑focused education
, and a demonstrated belief in mentorship, human connection, and personalized learning. Location & Travel:
U.S.-based, remote, with ability to travel periodically for site visits, Adventures events, and leadership meetings. Preferred Qualifications
Experience scaling academic programs
in a multi‑state online or hybrid school system (e.g., growth from ~5,000 to 20,000 students). Colorado/BOCES regulatory experience
or experience working closely with charter authorizers, accreditation bodies (e.g., Cognia), or multi‑state charter networks. EdTech or instructional design leadership experience
, especially involving digital curriculum, learning innovation, or assessment systems. Background in
classical, liberal arts, or leadership‑focused education models
at scale. Demonstrated success building or improving
PD systems
for remote faculty and academic leaders. Experience leading
AI‑enhanced academic initiatives
, such as AI‑supported curriculum development, instructional coaching, or operational efficiency improvements. Track record of
cross‑functional leadership
with Technology, Operations, Enrollment/Marketing, and Finance teams. Advanced degree (M.Ed., Ed.S., Ed.D., or Ph.D.) in Education, Educational Leadership, Curriculum & Instruction, or related field. 12–18 Month Expected Outcomes
Academic model unified across WL markets & partners Online instructional quality measurably improves AI‑enabled teaching practices adopted in alignment with WL philosophy Adventures scaled with clear quality metrics Directors (Curriculum, Academic Programs, Adventures) performing at high levels Strong cross‑functional alignment with COO, CTO, CMO, CFO, CGO After meeting the eligibility requirements, benefits are available, including Health, 401(k) Retirement, Paid Holidays, and Paid Time Off. Salary Range Williamsburg Learning is an Equal Opportunity Employer
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The Chief Academic Officer (CAO) oversees the critical operations and functions that support the student experience at Williamsburg schools. This includes online academics, local in‑person adventures, curriculum, compliance, and accreditation. This role is a member of the Williamsburg Learning Executive Team and reports to the COO. Essential Duties (Top 5 Roles
The CAO will ultimately be responsible for each of the areas below, but will have assistance to help manage some of these areas: 1) Academic Experience
Enhance the quality, efficiency, and effectiveness of teaching and learning. Implement strategies to enhance student engagement, outcomes, and transformational learning experiences. Establish partnerships within the industry to enhance academic programs and support student success. 2) Programs & Faculty
Scale the academic program to serve all WL markets and partner schools. Direct the strategy and standards for recruiting, developing, and retaining excellent faculty and staff. Drive innovation in educational practices. Lead, manage, and hold accountable (LMA) the Director of Academic Programs. Communicate the vision of the curriculum to meet current and future educational needs. Foster collaboration with the Director of Academic Programs, Program Leaders, and the Director of Curriculum to enhance the existing curriculum and deliver a best‑in‑industry student experience. Drive innovation in curriculum design and technology adoption. LMA the Director of Curriculum. 4) Compliance & Policies
Ensure operational compliance of the Academics Department with Accreditors, partner charter school boards, Education ReInvisioned BOCES, and state and federal regulations. Strategize and direct the accreditation process at WL and its partner schools. Coordinate with school leaders on site visits, state reviews, and board inquiries to ensure effective communication and collaboration. 5) Oversee Williamsburg Adventures
Scale the adventures program to serve all WL markets and partner schools. Develop strategies and standards for quality adventures that foster local community and transformational learning experiences. Operate WAD as an autonomous business unit. LMA the Director of Williamsburg Adventures. Please note that this job description is not designed to cover or contain a comprehensive listing of the activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time, with or without notice. Minimum Qualifications
Senior Academic Leadership:
7+ years in K–12 academic leadership (e.g., CAO, CSO, VP Academics, Head of Schools, Director-level), including managing director‑level leaders. Online School Experience:
Led academics for an online or hybrid K–12 school/program serving
1,000+ students
(preferably multi‑state). Compliance & Accreditation:
Direct experience with K–12 compliance and accreditation (state reporting, audits, site visits; multi‑state exposure strongly preferred). Technology & AI:
Comfortable using data and educational technology to drive decisions, with
hands‑on experience implementing AI or emerging tools
in a human‑centered way. Mission Alignment:
Clear alignment with
classical / liberal arts / leadership‑focused education
, and a demonstrated belief in mentorship, human connection, and personalized learning. Location & Travel:
U.S.-based, remote, with ability to travel periodically for site visits, Adventures events, and leadership meetings. Preferred Qualifications
Experience scaling academic programs
in a multi‑state online or hybrid school system (e.g., growth from ~5,000 to 20,000 students). Colorado/BOCES regulatory experience
or experience working closely with charter authorizers, accreditation bodies (e.g., Cognia), or multi‑state charter networks. EdTech or instructional design leadership experience
, especially involving digital curriculum, learning innovation, or assessment systems. Background in
classical, liberal arts, or leadership‑focused education models
at scale. Demonstrated success building or improving
PD systems
for remote faculty and academic leaders. Experience leading
AI‑enhanced academic initiatives
, such as AI‑supported curriculum development, instructional coaching, or operational efficiency improvements. Track record of
cross‑functional leadership
with Technology, Operations, Enrollment/Marketing, and Finance teams. Advanced degree (M.Ed., Ed.S., Ed.D., or Ph.D.) in Education, Educational Leadership, Curriculum & Instruction, or related field. 12–18 Month Expected Outcomes
Academic model unified across WL markets & partners Online instructional quality measurably improves AI‑enabled teaching practices adopted in alignment with WL philosophy Adventures scaled with clear quality metrics Directors (Curriculum, Academic Programs, Adventures) performing at high levels Strong cross‑functional alignment with COO, CTO, CMO, CFO, CGO After meeting the eligibility requirements, benefits are available, including Health, 401(k) Retirement, Paid Holidays, and Paid Time Off. Salary Range Williamsburg Learning is an Equal Opportunity Employer
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