Your first 90 days as a new head of school: what to read, which records to find, and how to judge the software you inherited

The first month: what to read, in the order it binds

Read before you decide anything. Each document below is a promise the school has already made to someone, and the promises bind you from the day you start.

1. The family handbook and the enrollment agreement, together. The handbook says what the school does; the agreement says what a mother or father signed and can hold you to: tuition and the payment schedule, the withdrawal and refund terms, the discipline ladder, the dress code, how records are released, what the school may photograph. Mark every place the two disagree. Those are the disputes you will have this year.
2. The staff handbook and every employment contract. Who is paid what, through when, with what notice; who evaluates whom; what the school promised about planning time, class sizes and training. A small school's staff handbook is often a draft from the founding year. Read it as the staff read it, which is literally.
3. This year's budget beside last year's actuals. Tuition revenue against the enrollment it assumed; financial aid as a total and as a share of tuition; the three biggest expense lines; what the budget calls contingency. If the school files a Form 990, the last one is a public document and your fastest honest picture of the money. A school affiliated with a church may file none, and then the treasurer's year-end statement is the document.
4. Twelve months of board packets and minutes. What the board was told, what it decided, and what it deferred. A deferred item is a decision waiting for you. Read the minutes backwards from the meeting that hired you.
5. The lease, or the agreement with the church. Term, rent, which rooms when, who repairs, who insures, and the notice to leave. If it is a handshake, writing it down is a first-quarter task.
6. The scholarship and ESA paperwork, if the school takes state money. The program's handbook, the school's attestations and vendor registration, the testing it promised, and the dates by which it must confirm enrollments and report withdrawals. These carry money and deadlines, and the deadlines do not know you are new.
7. The accreditation report or self-study, the insurance policies, and the last audit or financial review. Each one is someone outside the school describing it to you.

The second month: the records to find, and the test for each

Every record below has the same test: could the office produce it today, for any child, without asking a teacher to remember? Where the answer is no, that is the work, whatever the software.

• Transcripts. For every student in ninth grade and above: each course, term, mark and credit; the grade scale behind the marks; the credit rule (per grading period, or one final grade per year); honors weighting if any; and transfer credit named with the school that issued it. Print one senior's transcript and check it against last June's report cards. If the two disagree, finding out why is the registrar's job for the year.
• Attendance history. One mark per child per school day, by year, for the years the state or a scholarship program can ask about. Florida's scholarship audit procedures, for one, check that attendance was taken on a random day each quarter and observe ten students on an unannounced visit. If attendance lives in a teacher's planner, it does not exist.
• Health files. An immunization record or a documented exemption for every child, since state law sets school vaccination requirements and the state will ask; the allergy list and the medication orders where every adult in the building can see them; emergency contacts a mother or father confirmed this year, not at enrollment.
• Aid awards. Every award for the year: the family, the child, the amount or percentage, the year it applies to, who decided it, and whether it is the school's money or a third party's. ESA and scholarship money recorded as a discount is the usual reason a small school's receivables do not reconcile.
• The signed enrollment agreements and the roster. One agreement per family for this year, and a roster whose entry and withdrawal dates match them. A child on the roster without an agreement is a conversation; a withdrawn child still on the roster is an invoice.
• The records-release log. Who asked for a student's records, what was sent, and when. If the school has never kept one, start it the day you arrive: the duty to record disclosures lasts as long as the records do, and the requests come from the families who leave.
• Discipline records and service plans. The incidents the handbook's ladder says were recorded, and the IEP, 504 or therapy plans with their review dates and the name of whoever holds the authoritative copy.

Judging the software you inherited: eight questions for one week

Ask them in this order. The first three decide whether you have a system at all.

Score it honestly. A system that passes six of the eight is one to keep this year, and the two it fails are projects. A system that fails the first three is not a system, whatever it is called.

Deciding whether to move

Who each system is actually for

Read straight from our comparison pages, so a correction there corrects this. Some of these are the right answer for the school you inherited, and several cost less than we do.

NavEd

Microschools, co-ops and hybrid programs that want a gradebook, attendance, transcripts and a parent portal at the lowest published price, and don't need a lending library, equipment booking, volunteer check-in or records escrow.

SchoolCues

Small schools whose hardest job is reaching families — text alerts, yearbooks, alumni — and who don't mind asking for a quote rather than reading a rate off a page.

QuickSchools

Schools of 40 students and up that want a conventional SIS at the lowest published per-student rate and don't mind that report cards and the parent portal sit one tier up.

Skooly

Enrichment, tutoring and activity-based programs whose job is scheduling, bookings, attendance and billing rather than a permanent academic record — no report cards, no transcripts.

Gradelink

Private schools of 75–400 students that want a conventional SIS and will pay separately for online enrollment.

FACTS SIS (formerly RenWeb)

Private schools of 200+ students with business-office staff, need-assessed financial aid, and time for a quoted, module-by-module implementation.

ClassReach

Private K-12 schools that want online homework and text alerts in the same system as records and billing, and don't mind learning their price from a quote after a demo.

Blackbaud K-12 Solutions

Established independent schools with a development office, an audited general ledger and enough staff to run an implementation.

Sycamore School

Independent schools of 100–400 students that want per-student pricing and integrated payments.

TeacherEase

Schools focused on standards-based grading with a handful of teachers, especially where per-teacher pricing beats per-student.

Alma SIS

Independent and charter schools of 150+ students that need district-style state reporting and have time for quote-based buying.

Google Classroom

Distributing and collecting classwork, especially if your school already lives in Google Workspace.

ThinkWave

Schools on the tightest budgets that mainly need academics: gradebook, report cards, transcripts.

Jupiter Ed

Schools that want a teacher gradebook with LMS features and don't need admissions, a library or volunteer tracking.

Transparent Classroom

Montessori programs whose core need is tracking lessons presented and mastered, Montessori-style.

Procare Solutions

Child care centers, preschools and Head Start programs staying early-childhood — ratios, subsidies, meals and daily reports, with no graded class on the way.

CohortLedger

An ESA-funded microschool or learning pod in one of its nine states whose back-office pain is the quarterly disbursement cycle, and whose academic records live somewhere else.

Spreadsheets & the DIY stack

A new school's first semester with fewer than about ten students, before records, billing and parent access all need the same source of truth.

Moving to a system you chose, over a weekend

Moving in from another system, records and all, takes a weekend, because the long pole is the old system's export and your reading of it, not the new system's screens. This is the order that works in Pearspark, and most of it is the order that works anywhere.

1. Friday: export. Pearspark's importers carry presets for FACTS SIS (RenWeb), Gradelink, PowerSchool SIS, QuickSchools, Clever SFTP files, OneRoster CSV (Alma and others), Sycamore School, Procare, Brightwheel, Blackbaud Education Management, Jupiter Ed, TADS (VenturEd) and MySchoolWorx, and each preset names the report to run in the system you are leaving, which is the half most migrations fail on. Run the student export, the academic history or transcript export, the attendance export and the health export, and put them in one folder.
2. Saturday morning: students and families. Import the roster first. The preview shows every row before anything is written: which columns it placed, which it could not, which children it matched to a mother or father already on file, which dates read two ways. Fix the file, not the preview, and run it again.
3. Saturday afternoon: academic history, attendance, health. Transcripts import per student with the issuing school named, so a child who came from another school keeps that school's name beside the credit. Attendance history imports by day and feeds the attendance summary and the report card. Health records import through the same kind of preview, and an unknown column is reported, never silently dropped.
4. Sunday: aid, the gradebook, the portal. Settlement reports from ClassWallet, Odyssey or Step Up import as payments against the right students and invoices; award decisions from FACTS, Clarity or SSS import as awards. A teacher's gradebook comes in as a grid, one row per student and one column per assignment. Then invite every family to the portal at once, and let them see their own child's record before you announce anything.
5. Monday: the shadow spreadsheets, retired one at a time, each after the report that replaces it has been run and checked by the person who kept the spreadsheet.
6. What Pearspark does not import, so you can plan for it: lesson plans, discipline histories, a per-student document store (there is none), standardized test scores, and the ledger. Those stay where they are or move by hand. If you get stuck, write to support@pearspark.com. A person answers, and there is no sales call.

The parts of Pearspark involved

Each page says what the feature does today and what it does not.

Watch a move happen

Importing students, academic history, attendance and health records, inviting every family at once, and the board pack at the end of the first month. One short video each.