Dean of Parents

Young Founders School; New York, Northern (NY, KY); Hybrid; USD 180,000 - 240,000; Full time

Job summary

Founders School seeks a founding Dean of Parents to own the parent-facing experience, ensuring alignment, retention, and advocacy for every family. You report alongside guides and enrollment to shape the family lifecycle and maintain the school model with candor and decisive action.

You will handle escalations, coordinate community moments, and partner with the enrollment team to convert positive family experiences into referrals, while leveraging AI for sentiment tracking and personalized

Qualifications

• 10+ years owning high-trust relationships with ultra-high-net-worth families.
• Experience as GM or Hotel Manager in luxury hospitality or leading family offices.
• Clear, concise communication with founders, investors, and executives.

Responsibilities

• Holding the Standard: educate parents on AI-powered mastery learning and entrepreneurship; coach away from traditional-school expectations.
• Goal Alignment: run 30-minute goal meetings with families; turn vague aims into measurable goals.

Skills

High-trust relationships

Executive communication

AI fluency

On-site NYC work

Job description

Founders School is a four-year high school for ambitious teenagers who build real companies.

Our families are sophisticated, well-advised, and paying $150K/year. Many are founders, investors, or executives who have chosen this over every elite school in the country. They did not choose us for the amenities; they chose us because they expect this model to work, and they expect someone to tell them the absolute truth about how it's going.

We are hiring the founding Dean of Parents: the adult every Founders School family trusts, and the person who turns a cohort of demanding families into the most tight-knit, sought-after community in New York.

This is not account management, and it's not traditional event planning. This is a GM seat. You own trust: earning it, keeping it through hard moments, and turning it into advocacy. If you have run a luxury property or a private family office, you know the job. You fix a problem before the family knows it exists, you build rituals people talk about, and when an influential VIP asks for something that compromises the model, you say no so gracefully they thank you for it.

The Role

You own the parent side of Founders School. Every current family's alignment, retention, and advocacy runs through you. Reporting to Cameron Sorsby, you're the parent-facing co-leader alongside our Guides, the Head of Student Life, and the enrollment team. You take family issues off their plate so they can coach, and you make sure every family always knows who their person is.

When something goes sideways, it lands on you: a conduct issue, a boarding worry at 9pm, a parent who wants the curriculum softened for their teenager. You find the real concern, make the call, hold it and follow through until it stays resolved. You keep the family and you keep the model intact. Both.

You are visible: at drop-off, at private founding-family dinners, and on the phone the same day something matters.

What you will be doing

• Holding the Standard: Our model is demanding on purpose. You educate parents on AI-powered mastery learning and entrepreneurship, and actively coach them away from traditional-school expectations (homework, grades, lecture-style instruction).




• Goal Alignment: Running a 30-minute goal meeting with every family at the start of the year across our five pillars. You turn vague hopes into specific, measurable goals, log them where Guides can act on them, and follow up all year.




• Service Recovery & Escalations: When a conduct issue arises or a student's startup fails, you're on it. You partner with Guides to ensure families hear it from a person, fast.




• Building the Community: Designing the calendar of moments that make families feel part of something exclusive and meaningful: student demos, parent roundtables with investors, and small salons that connect families who should know each other. None of it is filler.




• Boarding Integration: Owning the boarding-family relationship alongside the Head of Student Life, ensuring parents outside NYC feel informed without having to chase updates.




• Guest Intelligence via AI: Using AI daily to run a parent-experience operation no traditional school could match: meeting prep, family profiles, update drafts, sentiment tracking, and follow-up that never slips.




• Advocacy & Retention: Running monthly focus groups, tracking family sentiment, flagging at-risk families early, and turning what you hear into concrete fixes. You partner with the enrollment team to turn happy families into our best referral engine.

What you will NOT be doing

• Capitulating to Keep the Peace: White-glove service here means candor and follow-through, not saying yes to everything. Retaining a family by quietly lowering the bar is failure.




• Admissions: Prospective families and enrollment decisions belong to the enrollment team. You partner with them only on current families.




• Teaching or Coaching: Guides, EIRs, and mentors own student academics and company building.




• Running Residential Life: Living in the dorms or running evening residential programming is Head of Student Life territory. You own the parent side of it.




• Event Planning for Event Planning's Sake: Every gathering exists to build trust, belonging, or advocacy.

What this becomes

At 6 months: Every family knows you by name and has had a goal meeting. The first signature community moments have run. Same-day service recovery is the norm, boarding parents feel informed, and every at-risk family has a plan.

At 12 months: The parent experience runs on a documented system: service standards, an escalation playbook, the community calendar, and sentiment tracking are all clear enough for a second campus to copy. The founding class re-enrolls at a high rate.

At scale: As Founders School opens more campuses, this seat becomes the standard for family experience everywhere. The path belongs to whoever proves they can turn demanding families into true believers.

Candidate requirements

• 10+ years personally owning high-trust relationships with ultra-high-net-worth families. You have served as a GM or Hotel Manager in elite luxury hospitality (Four Seasons, Aman, etc.), OR you have led private school advancement, a family office, or elite client service.




• A track record of holding firm decisions with demanding, influential people without losing the relationship. You can say "no" to a VIP and keep the standard intact.




• Clear, concise communication that earns confidence quickly with founders, investors, and executives. You are calm, direct, and over-communicate on anything that matters.




• Real conviction about AI-powered, mastery-based education, and the fluency to explain how it works, where it fails, and why it matters to analytical parents.




• You use AI across your work every day and can show how.




• You can work on-site in NYC, including early mornings, late afternoons, evening events, and occasional weekends.




• Authorized to work in the US without visa sponsorship. Background check required.

Do not apply if

• You need parents to like you more than you need them to trust you.




• You're uncomfortable telling a $150K/year family "no."




• You want a predictable 9–5 with no evenings, no weekends, and no phone calls that can't wait.




• You'd rather polish an experience than take ownership of outcomes.

The most ambitious teenagers in the country need parents who believe in what they're building. You can be the person who earns that belief.