The Opportunity: Teacher of Math

For the 2025-2026 academic year, we’re looking for a positive, enthusiastic educator who loves making complex math concepts click in a fun and engaging way and has the background and experience to teach all levels of mathematics, including advanced courses. This role goes beyond the classroom—you’ll be an active part of our community as an Advisor, Dorm Parent, and Coach, helping to shape students’ experiences both academically and personally.

Are you a passionate math teacher who can bring advanced high school math to life? We want someone who uses real-world examples, creative problem-solving, and even a bit of humor to spark curiosity and deepen understanding

What You Will Be Doing:

Teaching Math

• Unleash the magic of mathematics, teaching students not just formulas, but the power to solve real-world problems.

Inspiring  Engagement

• Create a vibrant learning environment by implementing meaningful project-based and experiential activities, aligning with 21st-century learning objectives. Encourage critical thinking, collaboration, creativity, reflective learning, and cross-disciplinary thinking.

Offering Diverse Instruction:

• Deliver instruction that transcends memorization, promoting understanding, application, analysis, evaluation, and creation. 
• Create personalized, one-on-one strategies and action plans for students who may be facing challenges in meeting learning objectives.

Assessing & Measuring Progress

• Measure student progress through various assessment models, aligning assessments with curriculum objectives and utilizing Bloom's taxonomy and rubrics.

Community Building:

• Cultivate a warm and welcoming residential environment that becomes a home away from home for students.
• Instill a strong sense of belonging and connectedness that promotes personal growth and mutual support.
• Inspire a sense of camaraderie that extends beyond the residential setting and into the broader school community.

Coaching Athletics

• Coach assigned athletic teams, planning and attending all practices, teaching strategies and techniques, and fostering sportsmanship throughout the season. (In lieu of coaching, other duties and responsibilities may be included that are commensurate with the successful candidate’s strengths and experience.) 

Building Relationships

• Build strong relationships with students, parents, and colleagues through regular updates, meaningful conversations, and constructive feedback.
• Participate fully in campus life, engaging in extracurricular activities to connect with students beyond the classroom.

Advising and Role Modeling:

• Advise students one-on-one regularly, addressing academic goals and promoting age-appropriate life skills such as interpersonal communication, conflict resolution, and time management.
• Act as a mentor and positive role model, reinforcing clear boundaries and guidelines, encouraging student autonomy and independence, and demonstrating transparency.

Growing Professionally

• Develop personal mastery by actively participating in professional development opportunities, networking to incorporate best practices, and staying updated with relevant professional publications.

Other Responsibilities:

• Perform any additional duties as required to contribute to the overall success of the students & the school.

You will be good at your job if you:  have a  Bachelor's Degree in Mathematics and can help students understand and apply mathematical concepts as well as mentor and motivate teenagers (the over and underachiever, the super-focused and the unfocused, the gifted and those with different learning needs). 

And you can:

• engage adolescent boys in learning in ways that manifest support, understanding, and empathy;
• empower and embody the Trinity-Pawling mindset through education, communication, and encouragement;
• incorporate differentiated instruction and project-based learning techniques;
• integrate a thoughtful pedagogy that aligns with the mission and vision of the School; 
• communicate clearly, effectively, and compassionately (orally and in writing) with students, parents, and colleagues; 
• deal effectively with ambiguity and change; 
• build relationships with students, parents, and colleagues;
• give and receive constructive feedback;
• demonstrate a clear interest in being part of a community that is committed to diversity and inclusion; 
• coach athletics and/or lead extra-curricular activities;
• establish and reinforce clear boundaries while being a positive role model for students;
• follow procedures by adhering to the School’s policies, 
• multi-task and meet deadlines,
• commit to the assorted various evening & weekend activities and responsibilities that occur on a routine basis,
• meet the physical demands which may include traveling on uneven terrain, climbing/descending stairs, standing for long periods of time, and carrying up to 50 pounds.

It will be helpful if you:

• have experience in an independent school setting and 2 years of teaching experience
• can teach higher-level math 
• understand and apply the concepts of social-emotional learning
• have experience coaching sports - especially football, hockey and/or tennis. 

Why you will like working here: 

• You’ll have an opportunity to influence young men - the future changemakers in our society.
• You can grow and develop professionally (tuition assistance, conferences, seminars, training, mentor program).
• You can be creative! Incorporate your gifts and talents in and out of the classroom to enhance the educational experience.
• We will take care of you with Medical, Dental, Retirement, and Life Insurance Benefits (just to name a few)
• Beautiful Campus, State of the Art Field House, Delicious Dining Opportunities
• Build relationships and develop lifelong friendships
• 60 miles from New York City and a 10-minute walk to the train station (did someone say Broadway?)
• Walking distance to a quaint village with Zagat-rated dining
• At Trinity-Pawling, you will be on top of the world!

All job offers are contingent upon the candidate’s successful completion of a background & fingerprint check, reference checks, pre-employment screening, as applicable. 

The annual salary range for this position is $40,000 - $65,000. This range represents our good faith estimate for this position.  We consider additional factors such as education, experience, skills as well the needs of the School at the time of the offer.

 

The Opportunity: Teacher of Spanish

For the 2025-2026 academic year, we are seeking a dedicated educator who can design and deliver a curriculum that emphasizes authentic communication, develops students’ linguistic fluency, and deepens their cultural understanding of the Spanish-speaking world. This role goes beyond the classroom—you’ll be an active part of our community as an Advisor, Dorm Parent, and Coach, helping to shape students’ experiences both academically and personally.

Teaching Spanish

• Develop and deliver engaging lesson plans that build proficiency in the four core language skills: reading, writing, speaking, and listening—with a strong emphasis on real-world communication and cultural context, as taught through storytelling and Comprehensible Input methodologies.
• Encourage students to express themselves confidently in Spanish through conversational practice, listening comprehension, and interactive speaking strategies.
• Foster a deep appreciation for the Spanish language and the diverse cultures of the Spanish-speaking world, incorporating literature, history, food, music, and traditions into classroom experiences.
• Cultivate cultural competence, helping students understand, respect, and connect with perspectives and practices from a variety of Hispanic cultures.

Mission, Vision & Strategic Alignment 

• Advance the School's mission by enthusiastically engaging in experiential and project-based learning, promoting, and contributing to the School's signature Institute programming, and actively supporting Winter Session initiatives.
• Support and advance the School's commitment to a student-centered environment by engaging in campus-wide mentorship and advocating for student growth and development.

• Participate in the continual assessment and iteration of signature programs to ensure innovation and excellence in boys' education.
• Collaborate with faculty and administration to enhance curricular offerings and optimize technology for a forward-thinking educational experience.

Advising and Role Modeling

• Advise students one-on-one regularly, addressing academic goals and promoting age-appropriate life skills such as interpersonal communication, conflict resolution, and time management.
• Serve as a mentor and positive role model, encouraging student autonomy, self-expression, and intellectual curiosity while maintaining healthy and professional boundaries.

Building Relationships

• Build strong relationships with students, parents, and colleagues through regular updates, meaningful conversations, and constructive feedback.
• Participate fully in campus life, engaging in extracurricular activities to connect with students beyond the classroom.
• Instill a strong sense of belonging and connectedness that promotes personal growth and mutual support.

Residential Life

• Foster a warm and supportive residential environment that becomes a home away from home for students.
• Supervise and engage with students in the residential setting, promoting personal responsibility, interpersonal skills, and community values.
• Facilitate activities and initiatives that build a sense of belonging and connectedness, encouraging personal growth and mutual support.
• Support students in their daily routines, including evening study sessions, dorm meetings, and informal check-ins.

Athletics and Extracurricular Involvement

• Coach assigned athletic teams, planning and attending all practices, teaching strategies and techniques, and fostering sportsmanship throughout the season and/or
• Engage with students beyond the classroom through regular participation and attendance  in extracurricular activities, school traditions, and community events

Your Qualifications & Strengths:

To thrive in this role, you will be fluent in Spanish, possess a Bachelor’s degree (Master’s degree preferred), have a deep understanding of Spanish and Latin American cultures, and prior teaching experience, ideally in an independent school setting

And you can: 

• engage adolescent boys in learning in ways that manifest support, understanding, and empathy;
• empower and embody the Trinity-Pawling mindset through education, communication, and encouragement;
• communicate clearly, effectively, and compassionately (orally and in writing) with students, parents, and colleagues; 
• deal effectively with ambiguity and change; 
• build relationships with students, parents, and colleagues;
• give and receive constructive feedback;
• demonstrate a clear interest in being part of a community that is committed to diversity and inclusion; 
• coach athletics and/or lead extra-curricular activities;
• establish and reinforce clear boundaries while being a positive role model for students;
• follow procedures by adhering to the School’s policies, 
• multi-task and meet deadlines,
• commit to  the frequent evening & weekend activities and responsibilities that occur on a routine basis,
• meet the physical demands which may include traveling on uneven terrain, climbing/descending stairs, standing for long periods of time, and carrying up to 50 pounds.

All job offers are contingent upon the candidate’s successful completion of a background & fingerprint check, reference checks, and pre-employment screening, as applicable. 

The annual salary range for this position is $40,000 - $60,000. This range represents our good faith estimate for this position.  We consider additional factors such as education, experience, skills as well the needs of the School at the time of the offer.

 

We are seeking a Manager of Advancement Services with Raiser's Edge experience to drive fundraising success by developing and executing smart strategies for database management, prospect research, and portfolio oversight. This means shaping clear protocols, streamlining processes, and setting objectives that align with organizational goals and the needs of a capital campaign. You'll also play a key role in supporting the creation of an annual operating plan designed specifically for advancement services. This hybrid position offers the flexibility to work both on-site and remotely.

What you will be doing:

Prospect Management:

• Partner with frontline fundraisers to create and implement effective strategies for identifying, qualifying, and tracking prospects through every stage of the donor lifecycle—from cultivation to stewardship.
• Analyze pipeline and prospect manager reports to uncover actionable insights that drive success.
• Lead pipeline and forecast reviews, portfolio strategy sessions, and prospect meetings to maximize fundraising potential and encourage collaboration across the team.

Prospect Research:

• Conduct in-depth prospect research, both proactively and reactively, interpreting complex financial and biographical data to guide informed fundraising strategies.
• Prepare detailed, actionable prospect profiles that give frontline fundraisers and senior leadership the insights they need to build meaningful donor relationships.

Data Management:

• Take the lead on researching, implementing, and managing software updates or CRM transitions to ensure systems run smoothly and data stays accurate.
• Perform regular database audits and establish clear processes to maintain data integrity.
• Ensure compliance with CASE/NAIS policies while customizing systems as needed—everything from managing user accounts to updating permissions.

Reporting and Analysis:

• Create accurate and timely reports, queries, and exports to support the Advancement Office and other departments.
• Use data analytics to spot trends, refine engagement strategies, and set realistic, data-driven fundraising goals.

Management, Training, and Development:

• Oversee the Gift Processing Associate.
• Train new staff members on fundraising systems and tools, making sure everyone feels confident and empowered to use them effectively.
• Provide ongoing support, mentorship, and resources to help the team continually grow their skills in database management and prospect research.

Continuous Improvement and Professional Development:

• Stay on top of industry best practices, seek out professional development opportunities, and benchmark against peer institutions to keep our Advancement efforts cutting-edge and effective.
• Perform any additional duties as required to contribute to the overall success of the students and the school.

Role Modeling:

• Inspire a culture of philanthropy and collaboration by being a positive role model. Set clear boundaries and expectations, encourage autonomy and independence, and always act with transparency and integrity.

Your Qualifacations & Strengths

• Hold a Bachelor’s degree in a relevant field and have experience in database management and prospect research/management, ideally in an educational or nonprofit setting.
• Are a pro at working with fundraising CRM platforms, wealth screening tools and databases, with hands-on experience in Raiser’s Edge/NXT is strongly preferred. 
• Have an intuitive understanding of how databases work, allowing you to navigate and analyze data efficiently.
• Possess strong analytical skills, enabling you to interpret and work effectively with complex data sets.
• Are comfortable working remotely and have the skills to stay connected, engaged, and productive in a virtual environment as well as able to report to the School on a periodic basis for in-person collaboration. 
• Stay calm and composed under pressure, tackling challenges with a level-headed and unflappable approach.
• Bring excellent organizational skills to the table, ensuring projects and priorities stay on track.
• Communicate effectively and confidently, whether you’re collaborating with a team or presenting findings to stakeholders.

And you can:

•  Inspire teamwork, trust, and accountability within the School’s fundraising efforts.
• Promote the mission of Trinity-Pawling and champion a culture of collaboration and shared success in all fundraising activities.
• Safeguard confidential information with the utmost integrity and discretion.
• Recommend and implement best practices to elevate the School’s development efforts.

If you’re tech-savvy, detail-oriented, and passionate about supporting an institution with a meaningful mission, this role could be a great fit for you!

The salary range for this position is $62,000 - $75,000. This range represents our good-faith estimate for this position. We consider additional factors such as education, experience, skills as well as the needs of the School at the time of the offer. All job offers are contingent upon the candidate's successful completion of a background & fingerprint check, reference check and pre-employment screening as applicable. 

We call ourselves The Pride:  

Established in 1907, Trinity-Pawling School proudly stands as an all-boys college preparatory institution nestled in the picturesque town of Pawling, New York, just 60 miles north of the vibrant city of New York. We are a close-knit community, wholeheartedly supporting one another as we pursue our individual and collective aspirations. Our student body hails from diverse corners of the nation and the world, creating a rich tapestry of cultures and backgrounds.

At Trinity-Pawling, we treasure the development of leaders, the formation of lasting friendships, the cultivation of athletic prowess, and the nurturing of global citizenship. Our campus offers a diverse array of opportunities, from a working farm to state-of-the-art maker spaces, winding mountain bike trails to a tranquil pond house classroom, allowing our students to deeply connect with the natural world and learn through hands-on experiences.

Furthermore, we take immense pride in our membership in the prestigious Founder's League, a nationally recognized association that stands as a testament to our commitment to excellence and competitiveness in the realm of education and athletics.

To meet the ever-growing demand for our exceptional educational offerings, we are excited to announce our search for a dynamic, results-oriented Associate Director of Admissions to join our team, starting sometime in August 2025. We look forward to welcoming an enthusiastic individual who shares our passion for providing students with a transformative experience. 

Note: This position includes the possibility of campus housing. If housing is offered, the individual will have some residential life student-facing responsibilities. 

How You Will Help the School:

You will play a vital role in the school's mission by identifying and attracting mission-driven students who will thrive in our community. Your dedication, strong ethics, initiative, and tenacity will be instrumental in shaping the future of our school community.

What You Will Be Doing:

• Recruitment and Outreach: Develop and maintain relationships with independent educational consultants, feeder schools, and other key stakeholders to promote Trinity-Pawling School and attract potential students.
• Pipeline Development: Cultivate a robust pipeline of prospective mission-driven students from an array of sources including feeder schools, educational consultants, alumni networks, community partnerships as well as various admission events. 
• Goal Achievement: Contribute to the growth of the school by using effective enrollment strategies to meet and or exceed enrollment targets. 
• Interview and Evaluation: Conduct interviews, assess applicants, and evaluate their fit with the school's mission and values.
• Admission Processes: Manage all aspects of the admission process, from initial inquiry through enrollment, ensuring a smooth and supportive experience for prospective students and their families.
• Application Evaluation: Review and assess application materials, including transcripts, recommendations, and personal statements, to make informed admission decisions.
• Financial Aid Guidance: Assist families in understanding and navigating the financial aid process, ensuring that a diverse range of students can access our educational opportunities.
• Community Engagement: Act as an ambassador for Trinity-Pawling School, fostering a sense of community among prospective and admitted students, their families, and alumni.
• Data Analysis: Collect and analyze enrollment data to identify trends, challenges, and opportunities for improvement.
• Enrollment Strategy: In collaboration with the Director of Admission, develop and implement enrollment strategies for attracting and retaining students, including marketing campaigns, events, and outreach efforts while operating within the boundaries of ethical conduct and adhering to regulations. 
• Professional Growth: Develop personal mastery by participating in professional development, networking to incorporate best practices, and reading professional publications.
• Role Modeling: Promote the interest of students by being a good role model, establishing and reinforcing clear boundaries and guidelines, encouraging students’ autonomy and independence, and acting in a transparent manner.
• Performs other duties as required.

To excel in this role, you need creativity, a tireless work ethic, and a goal-driven mindset, along with a proven track record of success in admissions, enrollment management, or a related field. The ability to craft compelling presentations, skillfully weave facts and figures with narratives about day-to-day life and the school's mission, and work tirelessly to attract, recruit, and admit mission-driven students is key.

• Educational Background: A Bachelor’s degree along with  3+ years of experience in Admissions (preferred)
• Passion for Education: A deep connection to the mission of Trinity-Pawling and a genuine enthusiasm for education.
• Exceptional Communication Skills: Strong written and spoken abilities.
• Integrity and Drive: Strong ethics, determination, and initiative to exceed admissions goals.

Also, you can:

• successfully turn inquiries into enrolled students by providing information, answering questions, and addressing concerns, 
• provide high-level customer service via email, telephone, and face-to-face communications with prospective parents, students, consultants, feeder schools, and Trinity-Pawling’s wider network.
• work weekends, and evenings and travel nationally and internationally to actively promote the school to prospective families, feeder schools, and educational consultants.
• track performance by maintaining records of interactions, tracking prospective student progress through the enrollment process, and providing regular reports on engagement and conversion rates,
• showcase success stories of current students who have successfully aligned with the school's mission and achieved their academic and personal aspirations,
• articulate the unique value proposition of the school, emphasizing how it contributes to the fulfillment of the student's academic and personal goals,
• make diversity, equity, and inclusion shine in every step of the admission process,
• collaborate with colleagues in the admission office and other school departments to enhance the overall admission experience and contribute to the school's strategic goals,
• inspire our school community by clearly and enthusiastically articulating the school’s new strategic priorities and warmly supporting families through the admissions process,

Note:  When not traveling, it is the expectation that you will collaborate in person with colleagues and our community. It's essential to be an integral part of the community, engage with students, and participate in campus life in order to effectively tell our “story” to prospective families. While we prioritize in-person collaboration, we may consider a hybrid remote position for candidates facing geographical challenges.

Why you will like working here: 

• Empower Students: Get ready to make a direct and positive impact on the lives of our amazing students!
• Join Our Vibrant Community: You'll become part of a close-knit community that not only values you but also inspires friendship and a global outlook.
• Benefits: Enjoy a wide range of perks, including comprehensive Medical, Dental, Retirement, and Life Insurance Benefits, to name just a few.
• Work-Life Balance: We believe in the importance of your well-being, which is why we offer generous Paid Time Off and Summer Hours so you can recharge and enjoy your downtime.
• Scenic Surroundings: Our campus is simply stunning, providing a beautiful backdrop to your workday.
• Fitness and Fun: Stay fit and active with access to our state-of-the-art Field House equipped with weights, a Cardio Room, and more. Plus, take advantage of our hiking and biking trails or relax by the pond during breaks.

The salary range for this position is $60,000 - $70,000. This range represents our good faith estimate for this position.  We consider additional factors such as education, experience, skills as well the needs of the School at the time of the offer.  All job offers are contingent upon the candidate’s successful completion of a background & fingerprint check, reference checks, and pre-employment screening, as applicable

 

Trinity-Pawling School seeks a dynamic and relationship-driven Parent Giving and Engagement Officer to lead our parent engagement and fundraising initiatives. This is a unique opportunity for a strategic connector—someone who naturally builds trust and fosters community—to play a key role in strengthening the School’s culture of philanthropy.

As a visible and active presence on campus, the Parent Giving and Engagement Officer will cultivate meaningful connections between current families, families of alumni, and the broader Trinity-Pawling community while designing and executing a comprehensive parent giving and engagement program.

What You Will Be Doing 

Fundraising & Parent Giving

• Lead all aspects of parent philanthropy, including messaging, segmentation, forecasting, identification, qualification, cultivation, solicitation, and stewardship—anchored in a donor-centered philosophy.
• Manage a portfolio of 75+ major gift donors and prospects, cultivating relationships to secure leadership-level support.
• Use data analysis, relationship insights, and prospect research to drive tailored cultivation and solicitation, in collaboration with frontline fundraisers and other Advancement team members.
• Collaborate on Annual Fund solicitation initiatives, such as Giving Days, end-of-calendar/fiscal year giving, etc.
• With support from Advancement team members and Communications, develop and deliver gift proposals, concept briefs, presentations, and other solicitation materials, as well as draft pledge agreements and statements of intention to give, as needed.
• Grow and support a robust parent volunteer program, and recruit, train, and steward volunteers in both fundraising and non-fundraising roles.
• Develop and grow the student philanthropy and engagement program.
• Ensure accurate tracking of parent giving, communications, and engagement in the School’s Advancement CRM (Raiser’s Edge).

Events & Stewardship

• Envision, plan and execute signature parent events and programs such as Family Weekend, Senior Parent Dinner, and special events, as well as regional community gatherings.
• Oversee event logistics: venue selection, vendor coordination, guest registration, attendee research, and day-of execution.
• Analyze event participation and impact to refine future strategies.
• Collaborate with Communications to promote events across digital channels, including social media and email.

Parent Engagement & Community Building

• Serve as a key liaison for the Pride Parents’ Association, fostering inclusive participation and parent leadership.
• Develop and distribute the bi-monthly Pride Post, highlighting student achievements, campus life, and community updates.
• Build relationships with parents and parent volunteers to encourage involvement and deepen their connection to Trinity-Pawling.
   

Philanthropic Education & Awareness

• Create opportunities to educate parents on the impact of giving and the School’s philanthropic priorities.
• Share compelling stories of students, alumni, families of alumni and students, and donors that demonstrate the mission in action.
• Promote a culture of generosity through thoughtful messaging, events, and personal outreach.
   

Campus Integration & Role Modeling

• Be an engaged member of the School community by participating in daily life, attending events, and modeling relational leadership.
• Model professionalism, integrity, and healthy boundaries in interactions with students, colleagues, and alumni.
• Perform other duties as assigned to support the success of the Advancement team and the broader School.

Professional Development & Innovation

• Stay current on trends and best practices in advancement, parent engagement, and independent school fundraising.
• Participate in conferences, workshops, and peer learning to enhance effectiveness and innovation.

Qualifications & Strengths

You bring a balance of emotional intelligence, strategic thinking, and enthusiasm for education. Key qualifications include:

• A Bachelor’s degree and 3-5 years of experience in advancement, parent engagement, or nonprofit fundraising (independent school or higher education experience is a plus).
• Demonstrated ability—or clear willingness to learn—to solicit gifts at the five-figure level and above, as well as building and managing donor relationships.
• Proven success in cultivating relationships and securing support from donors or constituents.
• Proficiency with CRM platforms (Raiser’s Edge preferred) and a data-informed mindset.
• Excellent written and verbal communication skills; able to craft compelling stories and persuasive appeals.
• A collaborative and inclusive approach to team and community engagement.
• A desire to be a visible, approachable, and trusted presence on campus.

Additional Expectations

• Willingness to work evenings and weekends, and to travel occasionally for events or donor visits.
• Ability to meet the physical demands of the role, including lifting up to 50 pounds and navigating campus terrain.

Personal Attributes

• Relational & Strategic – You understand people and how to inspire them toward shared goals.
• Collaborative – You enjoy teamwork and thrive in cross-functional settings.
• Mission-Driven – You’re passionate about education and the transformative power of giving.
• Tech-Savvy & Insight-Oriented – You leverage technology and data to guide decision-making.
• Professional & Personable – You bring both polish and warmth to your role.

The salary range for this position is $62,000 - $75,000. This range represents our good-faith estimate for this position. We consider additional factors such as education, experience, skills as well as the needs of the School at the time of the offer. All job offers are contingent upon the candidate's successful completion of a background & fingerprint check, reference check and pre-employment screening as applicable. 

Trinity-Pawling seeks a dynamic Alumni Giving and Engagement Officer to lead alumni fundraising and engagement efforts. This individual will strengthen relationships within our alumni community, foster a culture of philanthropy, and collaborate across departments to advance the School’s mission.

This is a role for a relational leader and strategic thinker—someone who thrives in a mission-driven environment and understands the power of connection.

What You Will Be Doing:

Fundraising & Alumni Giving

• Lead all aspects of alumni fundraising, applying a donor-centered approach to messaging, segmentation, forecasting, identification, qualification, cultivation, solicitation, and stewardship.
• Manage a portfolio of 75+ major gift donors and prospects, cultivating relationships to secure leadership-level support.
• Personalize cultivation and solicitation strategies using data analysis, relationship insights, prospect research, and collaboration with frontline fundraisers and other advancement team members.
• With support from Advancement team members and Communications, develop and deliver gift proposals, concept briefs, presentations, other solicitation materials, as well as draft pledge agreements and statements of intention to give, as needed.
• Support class giving, especially among milestone Reunion classes, and collaborate on Annual Fund solicitation initiatives, such as Giving Days, end-of-calendar/fiscal year giving, etc.
• Build and sustain a robust Class Agent Program to empower volunteer-driven giving and engagement.
• Identify, qualify, and cultivate new prospects to strengthen the major gifts pipeline.
• Maintain accurate donor records and engagement history in the Advancement CRM.
   

Engagement Events & Stewardship

• Envision, plan and execute key alumni events and programs, including Reunions, the Hubbard Hoops Classic, and other special alumni events.
• Travel regularly to meet alumni and families of alumni across the country, deepening relationships through one-on-one visits, small group receptions, and strategic engagement opportunities.
• Manage event logistics: venue booking, vendor coordination, registration, and on-site support. 
• Partner with Communications to promote events through social media, email marketing, and other channels.
• Use data to analyze event outcomes and continuously improve engagement strategies.

Engagement Strategy 

• Design and implement alumni engagement strategies that align with School priorities and deepen donor loyalty.
• Serve as a connector between alumni and the broader School community—students, faculty, staff, and families.
• Collaborate with colleagues across Advancement, Communications, and other departments to align fundraising and engagement.
• Foster a culture of philanthropy by creating opportunities for alumni to give, volunteer, and participate.

Education & Awareness

• Develop philanthropic education  initiatives to communicate the impact of giving and build understanding of fundraising priorities.
• Tell compelling stories of alumni, donors, and student experiences to inspire engagement.
• Promote a culture of giving through events, newsletters, and personal outreach.

Community Engagement & Citizenship

• Serve as an engaged member of the School community by participating in campus life and modeling a commitment to mission-driven leadership and authentic connection.
• Model professionalism, integrity, and healthy boundaries in interactions with students, colleagues, and alumni.
• Perform other duties as assigned to support the success of the Advancement team and the broader School.

Continuous Learning & Innovation

• Stay informed on best practices in advancement, alumni relations, and independent school fundraising.
• Engage in professional development and peer collaboration to refine and enhance strategies.

Your Qualifications & Strengths

You will thrive if you have both strategic acumen and a relational mindset to alumni engagement and fundraising. And: 

• A Bachelor’s degree and at least 3-5 years of experience in fundraising, alumni relations, or nonprofit development (independent school or higher education experience is a plus).
• Demonstrated ability—or clear willingness to learn—to solicit gifts at the five-figure level and above, as well as building and managing donor relationships.
• Familiarity with CRM systems (Raiser’s Edge preferred) and comfort using data to guide strategy and decision-making.
• Excellent written and verbal communication skills, with the ability to craft compelling appeals, proposals, and stories.
• A collaborative spirit and the ability to work across departments and stakeholder groups.
• A genuine interest in becoming an active and visible presence in the School community.

And You Can

• Willingness to work evenings and weekends, and to travel (up to 50%) for alumni events and donor visits.
• Ability to meet the physical requirements of the job, including standing for extended periods, navigating campus terrain, and lifting up to 50 pounds as needed.

Personal Attributes

• Relational & Strategic – You build trust and connection while aligning efforts with institutional goals.
• Collaborative – You value teamwork and enjoy cross-functional partnerships.
• Mission-Driven – You are inspired by the power of education and philanthropy.
• Tech-Savvy & Data-Informed – You embrace technology and use insights to guide your work.
• Professional & Personable – You bring warmth, humility, and high standards to all you do.
   

The salary range for this position is $62,000 - $75,000. This range represents our good-faith estimate for this position. We consider additional factors such as education, experience, skills as well as the needs of the School at the time of the offer. All job offers are contingent upon the candidate's successful completion of a background & fingerprint check, reference check and pre-employment screening as applicable.