The Right School
Changes Everything.
Founder-led 1:1 admissions advising for families seeking the nation's best private day and boarding schools. Expert strategy, authentic essays, integrated test preparation — all under one program, from first call to acceptance letter.
"ConnectPrep presented options I never thought of before. They opened up a world of opportunity."
Your Child Deserves a Strategic Advantage.
Private and boarding school admissions has never been more competitive. ConnectPrep brings founder-led expertise, a proven strategy, and genuine care to every family — from first call to acceptance letter.
Founder-Led Advising
Every engagement involves Jeremy Fine directly — not a junior associate. Families working at the Founder level get 20+ years of admissions insight applied to their specific child's application.
Deep School Knowledge
ConnectPrep advisors have worked with applicants to every major boarding and independent day school in the Northeast — from Exeter and Andover to Greens Farms, King, and Sacred Heart Greenwich.
Neurodiverse Expertise
Extensive experience with 2e students, IEP/504 holders, and families navigating accommodations. ConnectPrep helps identify schools with strong learning support programs and prepares students accordingly.
Integrated Test Prep
Unlike advising-only firms, ConnectPrep handles SSAT, ISEE, and HSPT preparation in-house — same team, same strategy. No coordination gaps between your advisor and your test prep tutor.
Regional Expertise
Deep familiarity with day and boarding schools across Fairfield County, Westchester, NYC, Long Island, and New Jersey. ConnectPrep knows the schools these families are applying to, and what each school values in an applicant.
Full-Cycle Accountability
ConnectPrep guides families through every stage — school research, test prep, essays, interviews, and decision day. One team, one strategy, clear milestones, and a single point of contact throughout.
Day School or Boarding School? We Help You Decide.
Many families are weighing both options simultaneously. ConnectPrep advises across both tracks — often helping families build a list that spans both day and boarding schools depending on fit, geography, and academic goals.
Day School Admissions
Day schools offer a rigorous private school education while students remain at home. Admissions is highly competitive, especially in markets like Fairfield County, Westchester, and NYC.
- Strong local community and parent networks
- Students live at home; greater family continuity
- Often highly selective in top markets (CT, NY, NJ)
- ISEE or SSAT required at most schools; TACHS/HSPT for Catholic schools
- Application includes essays, teacher recommendations, and parent statement
- Shadow days and campus visits are expected and evaluated
Boarding School Admissions
Boarding schools provide a transformative residential experience — deeper academics, wider extracurricular opportunities, and a national peer network that shapes students for life.
- Residential experience with strong peer and faculty bonds
- Access to collegiate-level resources and athletics
- National and international applicant pool — highly competitive
- SSAT is required at most; some schools accept ISEE
- Application includes student questionnaire articulating reason for boarding
- Campus visit and in-person or virtual interview is standard
Four Pillars of a Winning Application.
Every service is 1:1, fully personalized, and built around your child's unique profile and target schools. All four pillars work together as one integrated strategy.
School Selection & Application Strategy
Comprehensive guidance aligning your child's academic record, personality, extracurriculars, and goals with best-fit schools. We build the right list — not just a prestigious one.
- Personalized school matching and shortlisting across day and boarding
- Full application strategy and competitive positioning
- School visit planning, shadow day preparation, and campus etiquette
- Financial aid and scholarship strategy
- Waitlist management and supplemental materials
Essay Coaching & Personal Statement
We guide students through crafting essays that are authentic, specific, and memorable — tailored to what each school's admissions team is actually looking for in a candidate.
- Brainstorming sessions — finding the story worth telling
- Multiple draft reviews with substantive written feedback
- School-specific tone, voice, and prompt alignment
- Short-answer responses, activity descriptions, and parent statements
- Final polish for clarity, concision, and authentic voice
Interview Preparation
Structured mock interviews with real-time feedback build the confidence, presence, and ability to think clearly under pressure that elite school interviewers are looking for.
- Multiple full-length mock interview sessions
- Communication, eye contact, and presence coaching
- Question bank and response frameworks by school type
- School-specific interview preparation based on known formats
- Post-interview thank-you note strategy
Test Prep — SSAT, ISEE & HSPT
Targeted, strategic preparation for every private school admissions test — personalised to your child's baseline, learning style, and the specific exam required by their target schools.
- Full diagnostic before first session — section-level gap analysis
- Custom prep plan built around test date and score goals
- SSAT (Lower, Middle, Upper), ISEE (all levels), HSPT, and TACHS
- Multiple full-length timed practice exams with score tracking
- Accommodation support and IEP/504 testing strategy
Expert Local Knowledge Across the Tri-State Area.
ConnectPrep is headquartered in Westport, CT, with in-person and online advising serving families across the Northeast. We know the day and boarding school landscape in each region intimately.
Fairfield County, CT
Our home market. Deep familiarity with the competitive day school landscape and the boarding school pipeline in towns including Westport, Darien, Greenwich, New Canaan, Wilton, Ridgefield, and Westport.
Westchester County, NY
Strong relationships with independent school families across Scarsdale, Rye, Bronxville, Larchmont, Chappaqua, and surrounding areas. Familiar with both day schools and boarding school feeders in the region.
New York City
Serving families in Manhattan, Brooklyn, and the broader NYC metro navigating the competitive independent school admissions cycle — including ERB testing and the highly competitive specialized high school track.
Long Island, NY
Advising families in Nassau and Suffolk County applying to independent day schools and boarding schools. Familiar with both local private schools and the competitive boarding school funnel from the Island.
Northern New Jersey
Serving families in Bergen County, Essex County, and surrounding areas applying to independent day schools and top boarding schools. Particular expertise with the NJ Catholic school application (TACHS/HSPT).
Nationwide & International
All boarding school advising is available fully online. Families anywhere in the country — or internationally — can work with ConnectPrep on applications to Phillips Exeter, Andover, Choate, and other top U.S. boarding schools.
Jeremy Fine — Founder, ConnectPrep
Jeremy Fine founded ConnectPrep after more than 20 years working directly with students on test preparation, academic advising, and college and private school admissions. He has worked with hundreds of families across Fairfield County, Westchester, New York City, and beyond — guiding students into elite boarding schools, independent day schools, and top college programs.
Jeremy brings a rare combination of direct test prep expertise and admissions strategy under one roof. His approach is rooted in understanding each student as an individual — their strengths, their story, and the schools that will genuinely serve them. Families working in the Founder's Program receive direct, uninterrupted access to Jeremy throughout the application cycle.
From First Meeting to Acceptance Letter.
A structured, step-by-step framework — with clear milestones, expert coaching, and full accountability at every stage of the admissions cycle.
Free Consultation
A focused 30-minute strategy call with your advisor. We discuss your child's profile, goals, timeline, and target schools — and give honest guidance on what the process looks like for your family.
Diagnostic & School List
We assess academic history, test scores, extracurriculars, and goals to build a balanced school list — reach, strong match, and likely schools across day and boarding options.
Test Preparation
Strategic SSAT, ISEE, or HSPT prep begins — personalized plan, practice tests, and weekly progress tracking. Accommodation advocacy if applicable to your child's profile.
Application Strategy & Essays
We build a cohesive application narrative, guide each essay from brainstorming through final draft, and ensure consistency across all application materials for each school.
Interview Coaching
Multiple mock sessions with real-time feedback. Students walk into interviews articulate, confident, and prepared to reinforce the strengths of their application in person.
Decision & Enrollment
We help families evaluate acceptances, navigate financial aid packages, manage waitlists, and set students up for a strong start at their new school.
When to Start — and What to Expect.
Most families applying for fall enrollment should begin the process in winter or spring of the prior year. Here's a general guide to the private and boarding school admissions calendar.
Start School Research & Connect with ConnectPrep
Begin building your school list, researching fit, and starting SSAT/ISEE prep. Earlier preparation leads to stronger scores and a more considered school list. Ideal start point for most families.
School Visits & Test Registration
Schedule campus tours and open houses. Register for fall SSAT or ISEE test dates. Begin practicing with timed tests and section review. First draft of essays can begin in summer.
Applications Open — Essays, Recommendations & Testing
Most independent school applications open in September. Request teacher recommendations early. Complete final SSAT or ISEE testing by November. Essay drafts should be in progress.
Application Deadline Window
Most boarding and day school deadlines fall between January 1 and January 15. All materials — essays, recommendations, test scores, and supplemental forms — must be submitted by this date.
Interviews
Most schools conduct in-person or virtual interviews between January and February. ConnectPrep conducts final mock interview sessions during this window to ensure students are fully prepared.
Notification Day — "March 10"
Most boarding schools release decisions on or around March 10 — known in the admissions world as "Notification Day." Day schools may notify earlier. ConnectPrep supports families through decisions, waitlists, and enrollment choices.
Enrollment Reply Deadline
Families typically have until April 10 to accept an offer and submit an enrollment deposit. ConnectPrep helps families evaluate multiple offers and make the decision that is right for their child.
What Families Say About ConnectPrep.
Ride
Exeter was his first choice — and the full financial scholarship is a very unexpected blessing. It was an Everest of an undertaking. We poured ourselves into it. You guys helped us understand the task to get into boarding school and we see the necessary steps he needs to take to get into a top college. Good grades are not enough. He has created a unique and compelling path.
"Emily was accepted to Choate Rosemary Hall, Loomis Chaffee, Greens Farms Academy, Westminster, Sacred Heart Greenwich, and Kent School. ConnectPrep provided the perfect balance of test prep and admissions guidance."
"ConnectPrep presented options I never thought of before — forming a non-profit, taking online college courses, applying to internships. They opened up a world that has provided growth and a new perspective."
"Helped my son get into his top choice high school by acing the TACHS. Very knowledgeable — goes above and beyond to make sure students succeed and gain confidence in the process. Highly recommended."
"We needed help for our son who was overwhelmed. Jeremy came to the rescue with a study skills program that reduced his anxiety and built his confidence. He was a wonderful instructor and now our son has taken off, reaching his goals."
"Helped my daughter with the TACHS test and getting into her dream high school. Her grades improved tremendously. Very satisfied — 11/10 would recommend."
"ConnectPrep showed me a plan of action to help me confidently navigate all of my academic and test-prep options. My school counselor was not very accessible — CP filled that gap completely. I feel so confident now."
Everything You Need to Know About Private School Admissions.
Honest, specific answers to the questions ConnectPrep hears most from families considering private and boarding school advising.
Your Child's Future Starts with the Right School.
Book a free 30-minute strategy session. We'll discuss your child's goals, clarify target schools, and give you an honest picture of what the process looks like — no commitment required.