Director of Parent Relations
$400,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Multiple Locations, US
Semi-flexible schedule
In-person
full-time (40 hrs/week)
Long-term role

Director of Parent Relations   $400,000 USD/year

Description

You chose private school leadership because you wanted to influence how students grow and learn—not to manage fundraising campaigns or arbitrate parent councils. This role offers a structure where the educational philosophy is safeguarded for you, operational functions are centralized, and your time is dedicated to what you do best: engaging the most influential families, converting them into advocates, and serving as the authoritative voice when discussions become difficult.

Your responsibility will be to lead the parent engagement for Alpha within a single metro area—either Miami, San Francisco, or Los Angeles. Success will be defined by enrollment and advocacy: attracting prospective ultra-high-net-worth families and converting them, ensuring current UHNW families re-enroll and refer others, championing 2 Hour Learning publicly, and establishing Alpha as a recognized name locally. Approximately half of your time will be spent externally—developing community partnerships, hosting information sessions, and conducting one-on-one meetings with discerning parents who have reviewed every AI critique and expect to understand why this model is sound.

The remainder of your role involves serving as the final escalation point. When an Associate Dean of Parents encounters a situation beyond their ability to resolve—such as a prominent family threatening withdrawal or a campus quietly adjusting the model to appease a demanding parent—the issue escalates to you. You will retain the family while preserving the integrity of the model. Both outcomes are non-negotiable. Afterward, you will document the resolution so the Associate Dean network can manage similar situations independently in the future.

If you have led a private or independent K-12 institution, or if you have built a career cultivating trust with UHNW families in another sector, and you have been seeking a position where judgment and persuasion are the core outputs, this role is designed for you.

What you will be doing

  • Developing local visibility by forming partnerships with family offices, private clubs, and independent advisors, and hosting workshops and community events that drive inbound interest
  • Overseeing the entire admissions process for affluent families: conducting information sessions, managing 1:1 follow-up through the CRM, and making enrollment decisions, including advising a family when the school is not the right fit for their child
  • Transforming enrolled parents into vocal advocates for 2 Hour Learning by organizing advocacy workshops and facilitating parent-to-parent networks, ensuring that current families become your most effective source of new leads
  • Handling escalations beyond the scope of others: determining whether the issue stems from the model, campus implementation, or family alignment, engaging directly with the family, and then documenting the resolution for use across the network
  • Maintaining close relationships with current families through consistent engagement, and communicating recurring themes and insights back to leadership

What you will NOT be doing

  • Leading capital campaigns, donor cultivation efforts, major gift solicitation, or any other fundraising activities
  • Organizing PTAs, School Improvement Councils, parent committees, or focus groups that have decision-making authority over school policies
  • Overseeing facilities, finance, legal matters, vendors, technology, marketing, or community logistics—centralized teams manage all of these areas so your focus remains on relationships rather than operations
  • Developing curriculum or providing instructional coaching to staff on pedagogy; the academic model is owned and maintained centrally
  • Creating exceptions or modifications to the educational model to accommodate a parent's request, regardless of their influence
  • Merely logging and responding to complaints, or drafting newsletters and routine parent communications
  • Resolving conflict through avoidance—diplomacy in this role means delivering difficult messages, not lowering standards
  • Operating behind the scenes; this is a full-time, on-site, public-facing position that includes evening and weekend community events

Key responsibilities

Create a metro area where Alpha families become the most vocal advocates for 2 Hour Learning—and where no parent escalation is resolved by compromising the educational model.

Candidate requirements

  • 7+ years in a position centered on high-stakes relationships: head of school, fundraising, enterprise sales, private wealth management, or client success
  • Direct, sustained experience working with ultra-high-net-worth (UHNW) families, such as households with annual income of $1M+ or families paying full tuition at elite private schools
  • Experience in a parent-facing or client-facing capacity at an independent or private K-12 school, or within UHNW client services
  • At least one instance of personally guiding a sensitive situation to resolution: a parent crisis, a staff investigation, a press inquiry, or a regulatory interaction
  • A demonstrated history of upholding a standard in the face of pushback from influential individuals
  • Residing in the Miami, San Francisco, or Los Angeles metro area, and able to work on-site full-time, including evening and weekend events
  • Authorized to work in the United States without sponsorship

Nice to have

  • Current or recent Head of School—or a direct report to the Head—at a top-tier independent K-12 institution (NAIS-member or equivalent)
  • Experience in multi-campus or multi-site school leadership (regional director, network superintendent, COO of a school network)
  • A UHNW client-services background applied to school leadership: private wealth management, single-family office, or major-gifts development at an elite preparatory school or Ivy League institution
  • An established network among UHNW families or influential local organizations in Miami, San Francisco, or Los Angeles
  • Experience managing crisis communications involving press, regulators, or board-level stakeholders
  • Practical AI-building experience—custom GPTs, agents, or internally developed tools applied in a real operational setting
  • An advanced degree (M.Ed., MBA, or doctorate)—common among candidates in this profile, but not mandatory; no formal education is required for this role

Meet a successful candidate

Watch Interview
Chris Hayes
Chris  |  L2 Guide
United States

Ever wondered if work is enhancing your life, or erasing it? After years of late nights as a fitness coach left him exhausted and disconnect...

Meet Chris

Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About the role

About Crossover

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

The Olympics of work

It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.

Premium pay for premium talent

Premium pay for premium talent

Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.

Shortlist by skills, not bias

Shortlist by skills, not bias

We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join the world's largest community of  AI first Remote WorkersAI-first remote workers.