About Williamsburg Learning

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 Revenue Officer (CRO) at Williamsburg Learning leads the company’s efforts to expand its reach, reputation, and revenue through strategic oversight of brand, marketing, sales, customer service, and parent communications. This role is responsible for aligning marketing efforts with business growth objectives and ensuring consistent, high-quality experiences for both prospective and current families.

Essential Duties (Top 5 Roles)

1) Brand Strategy & Execution

Maintain and enforce WL’s Brand Brief and Brand Guidelines across all departments.
Oversee the creation and implementation of digital and physical brand assets.
Safeguard the integrity of WL’s visual and messaging identity.

2) Marketing Strategy & Execution

Develop and manage annual marketing and advertising strategies aligned with business goals.
Coordinate campaigns, websites, and social media in support of key initiatives.
Track and report performance on end-to-end marketing KPIs.

3) Sales Strategy & Oversight

Define and lead the sales strategy in collaboration with the Enrollment Advising Team.
Ensure consistent execution of sales systems and fulfillment of KPIs.
Align sales messaging with marketing materials and online assets.

4) Parent Experience Strategy & Communication

Oversee parent communication to ensure alignment with brand and sales strategies.
Manage the fidelity of the Start Process to support smooth handoffs to Academics.
Optimize website usability for current families as well as prospective students.

5) Customer Service Team Oversight

Lead the Customer Service Team, ensuring alignment with WL’s overall operations.
Maintain a consistent tone and approach across customer service touchpoints.
Evaluate team performance and drive improvement in family experience.

Non-Essential Duties

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

Bachelor’s degree in Marketing, Communications, or Business; MBA or Master’s preferred.
7+ years in marketing, with 2-4+ years in senior leadership/management roles.
Ability to develop business and marketing plans through the understanding of market dynamics.
Proven leadership experience in marketing, brand management, and sales strategy.
Firm grasp of digital marketing, martech, CRM, and data analytics.
Proficiency in market research, data analysis, and leveraging insights for decisions.
Exceptional written, verbal, and presentation skills.
Experience managing cross-functional teams.
Ability to integrate traditional, digital, social media, PR, and brand management across multiple departments and channels.

Preferred Qualifications

Experience scaling enrollment or demand-generation systems for online learning, charter schools, EdTech, or mission-driven education organizations.
Proven success leading multi-channel marketing strategies (paid media, SEO, content, partnerships, events) that drive measurable growth.
Background in classical education, liberal arts, or values-based educational models—or demonstrated passion for WL’s mission of developing principled leaders.
Strong capability in brand storytelling, especially for human-centered or purpose-driven brands.
Experience managing or integrating with Admissions/Enrollment teams to optimize conversion and customer journeys.
Proficiency with CRM, marketing automation, and AI-enhanced tools, using data to personalize messaging and improve efficiency.
Demonstrated success building high-performing marketing teams, including hiring, coaching, and scaling talent.
Experience in multi-state marketing or launching new geographic markets for educational programs.
Advanced degree in Marketing, Communications, Business, Education Leadership, or related field (preferred but not required).

12–18 Month Outcomes

Enrollment & Revenue:
Drives predictable enrollment growth that supports WL’s revenue and student count targets.
Brand & Messaging:
Clarifies and amplifies WL’s position as a leading classical, human-centered online learning provider, with messaging that matches WL’s voice and mission.
Marketing Engine:
Builds a multi-channel, data-driven marketing system (web, content, email, paid, partnerships) that reliably generates high-quality leads.
Marketing Admissions Alignment:
Creates a seamless funnel from marketing to admissions, improving conversion rates and supporting +80 “Proven Process” experience scores.
Team & Capability:
Hires and develops a strong marketing team, with clear roles, metrics, and a culture of experimentation and continuous improvement.
AI & Tools:
Implements AI-enhanced and automation tools in marketing to increase efficiency and personalization while maintaining a human, mission-aligned tone.
Cross-Functional Leadership:
Operates as a strategic thought partner on the Executive Team, ensuring marketing strategy supports WL’s long-term growth without compromising educational quality or human connection.

Benefits

After meeting the eligibility requirements, benefits are available, including Health, 401(k) Retirement, Paid Holidays, and Paid Time Off.

Salary Range

$150,000

Williamsburg Learning is an Equal Opportunity Employer

Williamsburg Learning

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