By Sagar Shankaran, Founder of CallSphere
The admissions associate, registrar, advancement and division head roles changed in 2026. What to teach a new hire in week one, and what to cut from the posting.
Key takeaways
Sixty-six percent of US small businesses now use AI in some part of their work, up from fifty-five percent a year ago. Independent schools sit inside that number whether or not the Head of School has said the word aloud, because the Advancement Associate has drafted donor letters with it since spring and the Grade 6 team has used it on trimester comments since November.
The number that should occupy a Head of School is the other one: roughly seventy percent of owners say their people need more training to use these tools well. The bottleneck stopped being the tool. It is the person — specifically the one you hire in June to start in July, twelve weeks before your first open house.
Independent-school hiring runs on a brutal calendar. The Admissions Associate resigns in April. You post in May, interview in June, and she starts the second week of July with an empty building, a Director of Enrollment Management on vacation until the 28th, and an October open house that will bring 60 families through the door. Onboarding is not a quarter-long program. It is three weeks in an empty building.
Here is what quietly changed about that new hire's first week. In 2023 you taught her the mail merge — Blackbaud or Veracross, how to build the constituent list, how the merge fields break when a family has two last names, how to test on yourself before sending 400 tour confirmations. Two days, and it was most of the job's technical content.
She does not need those two days now. What she needs instead is harder to teach and nobody has written it down: how to check what a machine wrote against the record before it goes to a family.
The job did not get easier. The verification step, which used to be built into the slowness of doing it by hand, now has to be taught as a separate skill with its own checklist.
The Admissions Associate. Was: typing tour confirmations, chasing missing transcripts and recommendation forms, formatting Notification Day letters, answering the inquiry line. Now: reviewing drafted correspondence, running the missing-document chase as an exception list instead of a spreadsheet crawl, and spending the recovered hours on the phone with families who visited and went quiet. Phone hours went up, not down. That is the point.
The Registrar. Was: transcript requests, immunization compliance in Magnus before the first day, enrollment verification letters, state reporting. Now: the same work, but the drafting and cross-checking happen first and she audits. She has also inherited the record of which systems touch student decisions, because she alone knows where every record lives.
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The Advancement Associate. Was: gift entry, acknowledgment letters within 48 hours, annual fund reminders, event lists. Now: the acknowledgment draft appears, and the judgment about which donor gets a handwritten line from the Head of School is still hers — and is now the larger part of the job.
The Division Head. Was: reading, editing and returning 340 trimester narrative comments in ten days, three times a year, most of it at the kitchen table after dinner. Now: the teacher drafts with help, the Division Head still reads all 340, and the faculty-meeting argument is whether a comment written with assistance is honest. Have that argument in August, not in the second week of the comment window.
The pattern below works, and the loop in the middle is not decoration. It is the whole training.
flowchart TD
A["Day 1: read-only access to the student file, no sending rights"] --> B["Day 2: drafts twenty tour confirmations, sends none"]
B --> C["Day 3: Registrar checks every draft against the record"]
C --> D{"Did anything not match the file?"}
D -->|Yes| B
D -->|No| E["Day 4: sending rights turned on for tour and open-house mail only"]
E --> F["Day 5: she writes the list of what never goes into a chat box"]
F --> G["Week 2: aid files, health records and discipline notes stay off limits"]
Two details make it work. The drafts go out under her name eventually, so she owns them from day one — nobody learns to check work they are not accountable for. And Friday's list is hers, in her words, not a policy handed to her. The Head of School countersigns it and it goes in the personnel file.
Take these off the job posting; they filter out good candidates for no reason. Advanced mail merge. "Strong Excel skills" as a proxy for competence. Formatting transcripts to the state template. Typing speed. Writing a serviceable paragraph of school marketing prose from scratch still helps, but it no longer separates the two finalists.
Put these on instead. Attention to a record: does she notice that the letter says Grade 4 and the file says Grade 5. Discretion: can she tell, unprompted, which of three documents should never leave the building. Phone presence with an anxious parent. Willingness to say "I don't know, I'll find out" to a family deciding where to spend $150,000.
What did not change: the enrollment contract still gets read line by line, the aid committee still meets in a closed room, and the reference check on a teaching hire is still a phone call. And if you use any tool to screen teaching applicants, the Illinois employment-screening rules that took effect 1 January 2026, and New York City's requirement for an annual bias audit and advance notice to candidates, apply to a school exactly as they apply to a bank.
Three sessions, forty minutes each, none taught by the tech director.
Session one, the Registrar: the record is the truth. Every fact in an outgoing message — grade, division, start date, tuition figure, spelling of a name — gets checked against the student information system before it goes. Show her two real examples of drafted text that was fluent and wrong.
Session two, the Business Manager: what never goes in. Financial aid applications and the tax returns attached to them. Anything from the health record. Anything about a custody arrangement. Anything a family said in confidence about a diagnosis, a divorce or a job loss. Not "be careful" — a named list of document types with a hard no.
Session three, the Director of Enrollment Management: what a family is actually buying. This session exists because assisted drafting produces prose that sounds like every other school's prose. In week one she needs to hear the four things that are true about your school and not true about the two schools you compete with, so she can put them back into every letter the machine flattens.
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The wrong way to justify this is "we won't need to replace her." You will. The honest number is how much of the first ninety days you get back. Illustration: 340 students, one admissions associate, $34 an hour loaded.
| Task, first 90 days | Old | New | Hours saved |
|---|---|---|---|
| Learning the merge and list building | 14 hrs | 2 hrs | 12 |
| Tour and open-house confirmations, ~380 | 26 hrs | 9 hrs | 17 |
| Missing-document chase, 180 applicants | 31 hrs | 12 hrs | 19 |
| Drafting the seven standard letters | 11 hrs | 4 hrs | 7 |
| New: verification and checking time | 0 hrs | 14 hrs | -14 |
| Net | 41 hrs |
Forty-one hours at $34 is $1,394, which is not the interesting part. The interesting part is when those hours fall: between mid-July and mid-October, exactly the window where a school either follows up with visiting families within 24 hours or does not. Put them on the phone with the eleven families who toured and went quiet, and one re-engages. That is worth more than the wage math.
The tour itself. A parent decides in the first ninety seconds inside your building, and she decides about the person walking beside her. Nothing about that changes.
The difficult call to a family whose child is not a match. That is a Division Head or the Head of School on the phone saying a hard thing kindly, and it determines whether that family speaks well of you for the next ten years.
The aid decision, and the conversation after it. Discretion is the entire product of a financial aid committee.
And the reference check on a teaching hire. Every school has met a candidate whose paperwork was flawless and whose former department chair told you everything in fifteen minutes. Do not automate that call.
Decide it in August with the whole faculty in the room, and write one page: what may be drafted, what must be observed and written by the teacher, and the rule that the teacher's name means she stands behind every sentence. Leave it unwritten and you get the worst of both — half the faculty using it guiltily, and a parent eventually noticing that two comments in the same packet share a phrase.
No, and a technical hire is usually the wrong instinct. The scarce skill in a school office is judgment about student records, not configuration. Train the Registrar and the Director of Enrollment Management properly, and let the tech director keep the network running.
That it is a week-one topic, not a requirement — and mean it. In a market where you compete with a district paying $12,000 more, screening on tool familiarity costs you good people for a skill you can teach by Friday. Screen instead on whether she catches the error in the sample letter you hand her in the interview.
By separating two things that get argued as one: what adults use for administrative writing, and what students may use on assignments. Different policies, different owners, different meetings. Conflating them is why the September faculty meeting runs ninety minutes over.
A closing note on the role most affected by all this. The front office is where a new hire either learns the school or drowns in the 7:50 phone crush. CallSphere builds AI voice and chat agents that answer the main line and web chat, book tours and capture inquiries around the clock — which for a July hire means her first month goes into learning families and records instead of juggling four ringing lines before the first bell.
Written by
Sagar Shankaran· Founder, CallSphere
LinkedInSagar Shankaran is the founder of CallSphere, where he builds production AI voice and chat agents deployed across healthcare, hospitality, real estate, and home services. He writes about agentic AI, LLM engineering, and shipping voice agents that handle real calls in production.
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