Employment at CSS

Director of Student Enrichment: The Colorado Springs School

Position Summary

The Colorado Springs School (CSS) seeks a dynamic, innovative, and collaborative Director of Student Enrichment. This 12‑month position leads three key areas:

• A traditional Athletic’s portfolio, with vision and leadership for all JK–12 athletics

• Auxiliary Programming that expands and energizes the school’s unique offerings

• Design and launch of CSS’s inaugural Homeschool Enrichment Program, including program development, logistics, and cross‑department collaboration

This role is ideal for a creative problem-solver who can build enthusiasm around distinctive athletic and enrichment experiences, strengthen community connections, and manage complex programs with clarity and care.

Key Responsibilities

1. Athletics Leadership

• Provide vision, leadership, and day‑to‑day oversight for all interscholastic and intramural athletic programs

• Recruit, hire, supervise, and evaluate coaches; foster a positive, student-centered athletic culture

• Develop athletic schedules, coordinate facilities and transportation, and manage game/event operations

• Ensure alignment of athletics with the school’s mission, core values, and academic program

• Oversee league and CHSAA compliance, eligibility, sportsmanship standards, and risk management

• Partner with communications and advancement to highlight student-athletes and promote CSS athletics

2. Auxiliary Programming and Innovation

• Design and oversee mission‑aligned auxiliary programs (e.g., camps, clinics, clubs, weekend/evening offerings, facility rentals) that showcase CSS’s distinctive strengths

• Identify and launch unique athletic and co‑curricular offerings that attract new families and deepen engagement among current students

• Build and maintain community partnerships to expand programming, facilities use, and brand visibility

• Collaborate with business and operations staff on budgeting, pricing, contracts, and revenue goals

• Use data and feedback to refine programs and pilot creative new initiatives each year

3. Homeschool Enrichment Program Development

• Lead the creation and launch of CSS’s inaugural Homeschool Enrichment Program from the ground up

• Design program structure, schedule, course offerings, and student experience in alignment with CSS’s philosophy

• Coordinate logistics including space use, staffing, calendar alignment, and daily operations

• Collaborate with admissions, communications, and business office to market the program, manage inquiries, support enrollment, and track retention

• Serve as primary point of contact for homeschool families; manage caseloads, communication, and ongoing support

• Monitor program quality, gather feedback, and adjust curriculum and operations to ensure high satisfaction and strong outcomes

Desired Qualifications

• Bachelor’s degree required; master’s degree in education, educational leadership, sport administration, or related field preferred

• Previous experience as an Athletic Director, assistant AD, or in significant athletic program leadership

• Demonstrated success designing or managing auxiliary, after‑school, camp, or enrichment programs

• Experience building programs from concept to implementation (e.g., new initiatives, schools, or divisions)

• Strong organizational skills with the ability to manage multiple programs, calendars, and constituencies

• Excellent communicator who can partner effectively with faculty, staff, families, and community organizations

• Proven track record as a creative problem solver who enjoys innovation and building momentum around new ideas

• Commitment to the mission, values, and educational philosophy of The Colorado Springs School

Personal Attributes

• Entrepreneurial mindset with the ability to build something new while managing existing programs

• Relational leadership style; enjoys being visible at events and connecting with students and families

• High level of integrity, professionalism, and follow‑through

• Enthusiasm for student development, athletics, and experiential education

Salary Range: $68,000–$72,000

To apply, please submit a cover letter, resume, and references to hr@css.org

Marketing and Communications Coordinator - The Colorado Springs School

The Colorado Springs School (CSS) seeks a dynamic, detail-oriented Marketing and Communications Coordinator to support the school’s internal and external communications, digital presence, and brand consistency. This position plays an important role in advancing the school’s mission by helping tell the story of CSS through newsletters, website updates, social media, publications, and schoolwide messaging. The Coordinator works closely with the Director of Enrollment Management and collaborates across departments to ensure clear, timely, and compelling communication.

Key Responsibilities:

• Develop and manage internal communications for families, students, faculty, and staff, including weekly newsletters, announcements, and other school communications.

• Assist with the planning, drafting, scheduling, and distribution of email communications from the Head of School, Admissions, and Advancement.

• Create, schedule, and publish engaging content across social media platforms in alignment with the school’s brand and voice.

• Maintain and update the school’s website, ensuring timely, accurate, and engaging content.

• Draft and distribute press releases, media communications, and other school publications as needed.

• Support the production and updating of school publications, including handbooks, event invitations, programs, and parent communications.

• Coordinate and manage workflows with external marketing partners and vendors, including oversight of outsourced digital advertising and social media campaigns.

• Support branding efforts by ensuring consistency in tone, visuals, and messaging across communication channels.

• Capture and curate photo and video content to support storytelling and marketing efforts.

• Track and report on key metrics related to website traffic, social media engagement, and campaign performance.

• Assist with time-sensitive or urgent communications as directed, including limited crisis or campus-wide messaging support.

• Collaborate with colleagues across departments to gather content, highlight student and faculty stories, and support enrollment and advancement priorities.

• Perform other duties as assigned in support of the Director of Enrollment Management and school leadership.

Qualifications:

• Bachelor’s degree in Marketing, Communications, Journalism, or a related field.

• 2–4 years of experience in marketing, communications, or a related role; independent school or nonprofit experience preferred.

• Exceptional writing, editing, and proofreading skills with strong attention to tone, clarity, and audience.

• Experience managing social media platforms and digital content.

• Familiarity with website content management systems.

• Experience working with external vendors or marketing agencies is preferred.

• Strong organizational skills and ability to manage multiple projects and deadlines.

• Basic knowledge of digital marketing tools, such as Google Analytics, email marketing platforms, and social media scheduling tools.

• Photography and/or videography skills are a plus.

Personal Attributes:

• Collaborative, proactive team player.

• Strong attention to detail and commitment to accuracy.

• Ability to maintain confidentiality and exercise sound judgment.

• Creative thinker with a passion for storytelling.

• Appreciation for and commitment to independent school education and community.

Reporting Structure:

This position reports to the Director of Enrollment Management and works closely with colleagues in Admissions, Advancement, and academic leadership.

Suggested Salary:

$48,000 to $60,000

To Apply:

Email application materials to hr@css.org

Application materials should include: Resume (with explicit connection to the Key Responsibilities), Cover Letter, and Professional References

Lower School Teacher Job Description

Roles and Responsibilities:

The role of our teachers will focus on instilling a love of learning. The Lower School teacher fosters children’s curiosity and innate desire to learn and understand the world around them. They create a secure environment to support learning and assist children with their growing independence. Teachers must be flexible, and creative, engaging, and establish freedom within structure. They will help children develop social skills and supervise them during meal times. Lower school teachers report to the Lower School Division Director.

The position’s preferred qualifications:

• Bachelor’s degree in elementary education or a closely related field. A graduate degree and a track record of successful teaching at the lower school level are preferred

• Firm understanding of academic, social, and emotional development

• Innovative mindset with strong skills in communication, collaboration, project-based learning, and technology

The knowledge, skills, and abilities required for the Lower School Teacher position:

Lower School teachers will need to create a positive and vibrant learning environment for students. The preferred candidate will have a strong desire to see their craft improve and evolve. The ideal candidate will possess a growth mindset and share their expertise openly with others. Lower School teachers will be able to kneel, crouch, work at a table/desk, and transition to and from the floor to work with students and may be required to lift up to 20 pounds.

The Lower School teacher candidate will:

• Shape the lives of children by using best teaching practices

• Collaborate effectively with co-teacher and other colleagues

• Use variety, creativity, and flexibility to motivate and inspire young learners

• Teach reading, writing, math, science, and social studies

• Facilitate social-emotional learning using elements of Yale’s RULER program

• Facilitate the development of a positive class culture that supports learning and personal growth using elements of Responsive Classroom

• Collaborate with the Learning Support Coordinator to support students with unique and diverse learning needs

• Provide regular and specific student feedback and maintain assessment records

• Communicate with students and families regularly

• Know the developmental and academic abilities of one’s students

• Effectively coordinate with co-curricular teachers (PE, drama, art, music, Spanish, library, choir, and band)

• Perform various student supervisory duties.

• Adhere to the standards described in the Employee Handbook.

• Perform other duties as assigned by the Head or Associate Head of School.

SALARY RANGE: Starting at $50,000 annually based upon skills and experience, excellent benefits package.

Please submit a cover letter, resume, and references to hr@css.org and indicate the grade levels you are interested in as multiple positions are available.

Head of School – The Colorado Spring School

Search Process & Timeline:

Opens: Monday, April 27

Closes: May 9

First Round Virtual Interviews: Sunday, May 10 and Monday, May 11

Final In-person Interview: Friday, May 15 and Saturday, May 16

• Candidates invited to the final interview should be prepared to be on campus on both days. A schedule will be provided prior to the interview.

• Final interviews may need to be held the week of May 25. This information will be communicated to the finalists the week of May 12 (if needed).

Position Summary

The Head of School serves as the chief academic and strategic leader of The Colorado Springs School (CSS), responsible for advancing the school’s experiential educational mission, fostering a strong and vibrant school culture, and leading the academic and community life of the institution.

Working in close partnership with the Chief Business Officer, the Head of School ensures that the school’s academic programs, faculty leadership, enrollment strategy, and community engagement are aligned with the institution’s mission and strategic priorities.

The Head of School focuses on academic leadership, institutional vision, and community engagement while working collaboratively with the Board of Trustees and Chief Business Officer to ensure that institutional goals are supported by responsible financial and operational planning.

Leadership Structure and Reporting

The Head of School reports directly to the Board of Trustees and serves as the primary educational leader of the institution.

The Head of School is expected to work in close partnership with the Chief Business Officer, incorporating financial insight and operational considerations into institutional decision-making

Key Responsibilities

Academic Leadership

The Head of School is responsible for the overall leadership and excellence of the school’s academic programs.

Responsibilities include:

• Setting and advancing the academic vision of the school

• Ensuring the quality and integrity of academic programs across all divisions

• Supporting curriculum development and instructional innovation

• Promoting a culture of experiential-based academic excellence and intellectual curiosity

• Ensuring alignment with accreditation standards and best practices in independent school education

Faculty Leadership and Development

The Head of School provides leadership for faculty recruitment, development, and evaluation.

Responsibilities include:

• Hiring, mentoring, and evaluating faculty and academic leaders

• Supporting professional development and instructional excellence

• Promoting a collaborative and supportive faculty culture

• Ensuring appropriate staffing levels based on enrollment and program needs

• Working to maintain strong academic leadership across the school

School Culture and Community Engagement

The Head of School serves as the primary ambassador for the school and plays a central role in maintaining the strength of the school community.

Responsibilities include:

• Fostering a positive and inclusive school culture

• Engaging actively with students, families, faculty, and alumni

• Representing the school within the broader community

• Supporting school traditions and community-building events

• Strengthening relationships with parents and stakeholders

Enrollment Strategy and Institutional Advancement

The Head of School works closely with the Director of Enrollment to support student recruitment and retention.

Responsibilities include:

• Partnering with enrollment leadership to support recruitment and retention strategies

• Supporting admissions events and community outreach

• Strengthening the school’s reputation and visibility within the community

Development and Fundraising

The Head of School plays an important leadership role in advancing the school’s culture of philanthropy and supporting the financial sustainability of the institution. Working in partnership with the Director of Development and advancement staff, the Head of School helps guide the school’s fundraising strategy and actively participates in development efforts.

Responsibilities include:

• Supporting the planning and execution of the annual fundraising program in collaboration with development staff and the Board of Trustees.

• Engaging directly with current and prospective donors to cultivate relationships and secure philanthropic support for the school.

• Assisting in the solicitation of major gifts that support institutional priorities, including scholarships, program initiatives, and capital improvements.

• Partnering with development leadership and the Board to strengthen relationships with alumni, parents, and community supporters.

• Serving as a visible ambassador for the school, helping communicate the mission, vision, and impact of CSS in ways that inspire philanthropic support.

Through these efforts, the Head of School helps ensure that fundraising and philanthropic engagement support both the immediate needs and long-term sustainability of the Colorado Springs School.

Strategic Leadership

The Head of School works with the Board of Trustees and leadership team to guide the long-term strategic direction of the school.

Responsibilities include:

• Helping shape and implement the school’s strategic plan

• Supporting innovation in programming and student experience

• Identifying opportunities for growth and program development

• Ensuring that strategic initiatives align with the mission and values of the school

Board Partnership

The Head of School serves as the primary liaison between the administration and the Board of Trustees.

Responsibilities include:

• Providing regular reports to the Board on academic programs and school operations

• Supporting Board strategic planning and governance initiatives

• Collaborating with the Board on long-term institutional goals

• Maintaining transparent communication regarding institutional priorities and challenges

Qualifications

Preferred qualifications include:

• Advanced degree in education or related field

• Demonstrated leadership experience in independent schools or similar educational institutions

• Experience managing faculty and academic programs

• Strong communication and community leadership skills

• Experience working with boards of trustees and nonprofit governance structures

• Experience in development and fundraising

Key Attributes

Successful candidates will demonstrate:

• A deep commitment to the mission and values of experiential-based independent school education

• Strong leadership and interpersonal skills

• Strategic thinking and visionary leadership

• Ability to build trust and foster collaboration across the school community

• Commitment to transparency and institutional stewardship

• An ability to support enrollment growth and retention through community engagement and program alignment

• Collaborative leadership style with a demonstrated ability to work effectively with senior operational leaders

• Demonstrated ability to align institutional priorities with financial realities

Impact of the Role

The Head of School plays a central role in ensuring that the Colorado Springs School continues to provide an exceptional educational experience for its students.

Through strong academic leadership and partnership with the Chief Business Officer and Board of Trustees, the Head of School will help guide the school toward a future that is both educationally excellent and financially sustainable.

Salary: $150,000 - $180,000 (with potential for incentive package)

To Apply: Email application materials to en.applicationhub@gmail.com

Application materials should include: Resume (with explicit connection to the Key Responsibilities), Cover Letter, and Professional References (minimum of five including current supervisor).

Roles and Responsibilities include, but are not limited to:

• Assist in promoting the safety, health, and comfort of students and employees by maintaining school buildings and grounds.

• Maintain a high standard of safety, cleanliness, and efficiency in all maintenance and repair projects.

• Perform preventive maintenance, repair, and installation in connection with:
  • a. electrical, plumbing, and HVAC systems (working in conjunction with licensed contractors).
  • b. exterior and interior of buildings.
  • c. school grounds.

• Move equipment and materials within and between school buildings.

• Work overtime when emergencies arise in order to prevent disruption of the schools.

• Act as a substitute custodian when necessary.

• Observe campus policies at all times.

• Keep abreast of new information, innovative ideas, and techniques.

• Adhere to all district health and safety policies, including all precautions of the

• Bloodborne Pathogens Exposure Control Plan.

• Other duties as assigned by the Buildings and Grounds Supervisor or Administrative Staff.

• Maintain school buildings and grounds in top condition to ensure full and productive use of campus facilities.

• Ensure that all activities conform to CSS/campus guidelines.

• Communicate effectively with all members of the school and community.

• React to change productively and handle other tasks as assigned.

• Appropriately operate all equipment and machinery as necessary.

The position’s preferred qualifications:

• High School diploma or equivalent.

• Experience in building and grounds operations.

• Familiarity with computers and software relating to maintenance and inventory.

• Ability to read chemical labels.

• Ability to read material safety data sheets (MSDS).

• Ability to initiate and complete work orders.

• Have a valid driver's license, be able to drive, and qualify under the campus insurance carrier when driving a district vehicle.

• Requires prolonged sitting or standing.

• Requires physical exertion to manually move, lift, carry, pull, or push heavy objects or materials.

• Requires stooping, kneeling, crawling, bending, turning, and reaching.

• Requires climbing and balancing.

• Must work indoors and outdoors year-round.

• Must work in noisy and crowded environments.

• Must work in and around dust, fumes, and odors.

• Must be able to work in high places.

Salary:

This position is a full-time position with a pay rate of $17 to $20 per hour based upon skills and experience.

APPLY: Email your cover letter and resume to: hr@css.org