Executive Operations Associate

AI • Research • Brokerage • Personal Support

The Roebling Team at Compass is building a technology-enabled luxury residential real estate brokerage centered around original research, artificial intelligence, data, and publishing.

Our platform includes thousands of residential building profiles, proprietary market research, The Roebling Index, The Roebling Report, interactive calculators, and AI-powered research workflows. We are expanding beyond Manhattan into additional luxury markets across the United States while continuing to grow our brokerage business throughout New York City.

We're looking for someone who enjoys bringing structure to complicated work. This is not a traditional Executive Assistant role. Instead, you'll work directly with the founder to help operate a growing business across brokerage, research, publishing, technology, and selected personal administration.

The objective is simple:

Protect the founder's time, improve operational efficiency, and help the business continue to compound.

Responsibilities

This position touches nearly every aspect of the business. Responsibilities will evolve over time but may include:

Executive Operations

Manage calendars, coordinate meetings, organize priorities, schedule travel, follow up on ongoing projects, maintain task management systems, organize documents, and assist with selected personal administrative responsibilities.

Brokerage Operations

Coordinate listing preparation, organize transaction files, prepare client presentation materials, maintain CRM records, manage marketing projects, coordinate vendors, conduct property research, and help ensure that active transactions and opportunities continue moving forward.

AI Research & Publishing

Use Claude as a daily work partner to conduct research, improve written content, organize information, maintain website content, publish market research, verify AI-generated output, improve prompts and workflows, document standard operating procedures, and identify opportunities to automate repetitive work.

Continuous Improvement

Look for better ways to organize information, simplify recurring processes, improve systems, and eliminate unnecessary work. We value people who naturally identify inefficiencies and enjoy solving operational problems.

Qualifications

We're less interested in formal credentials than in how you think and work.

The ideal candidate:

Writes exceptional English.
Naturally pays close attention to detail.
Enjoys solving unfamiliar problems independently.
Learns new software quickly.
Uses AI intelligently instead of relying on it blindly.
Produces polished work without constant supervision.
Communicates clearly and professionally.
Takes ownership of projects from beginning to end.

Real estate experience is helpful but not required.

Practical Skills Assessment (Required)

This assessment is the most important part of your application.

Rather than relying solely on interviews, we'd like to see how you approach unfamiliar work, solve problems, communicate, and use artificial intelligence in a real-world setting.

Please record your screen while completing the assignments below and narrate your thought process throughout. We are evaluating how you think, not simply whether you arrive at the correct answer.

Please submit:

One screen recording (approximately 20–30 minutes)
Your written deliverables

You may use any screen recording software you prefer.

AI Requirement

Claude must be your primary work assistant throughout this assessment.

You are encouraged to use Claude to:

Solve unfamiliar problems
Conduct research
Organize information
Improve writing
Troubleshoot challenges

You may also use publicly available resources to verify information.

We intentionally provide limited instructions. One of the most important parts of this role is learning how to use AI to independently solve unfamiliar problems.

Assignment 1 — Property Research & Owner Outreach

Your objective is to identify the owner(s) of a New York City property and prepare professional outreach.

Property Address

77 Sands Street
Brooklyn, NY

Using Claude and publicly available resources, determine:

Current ownership entity
Individual owner(s) behind the ownership entity (if publicly identifiable)
Ownership history (if applicable)
Mailing address
Phone number(s)

Email address(s), if available
LinkedIn profile(s), if available

If you cannot confidently verify any information, explain why.

Draft the Outreach

Write a professional email of 75 words or fewer that:

Introduces the team
Explains that you represent a prospective tenant interested in leasing space within the property
Requests a brief conversation
Offers to provide additional information if helpful

Then rewrite the same outreach as a LinkedIn message of 25 words or fewer.

Assignment 2 — Content Translation

Read the attached NYT article. ----------

Using Claude as your primary assistant, create a three-slide Instagram carousel inspired ---------- slide should include:

A short headline
One to three concise sentences
Original wording (do not copy the article)
A clear, professional tone

After creating the carousel, briefly explain:

What Claude initially produced
What changes you made
Why your final version is stronger

Assignment 3 — Website Review

Spend approximately ten minutes reviewing:

----------

Record your observations and tell us:

Three improvements you would recommend
Any factual inconsistencies you notice
Any usability improvements
Any operational improvements
Any opportunities where AI could improve efficiency

There are no right or wrong answers. We are interested in your thought process and your ability to identify opportunities.

Assignment 4 — Reflection

At the conclusion of your recording, answer the following questions:

What was the most challenging part of this assessment?
Tell us one thing Claude got wrong during the process.
How did you verify or improve Claude's output?
If you joined tomorrow, what would be the first process you would improve?

What We're Evaluating

Throughout this assessment, we're evaluating more than technical ability.

We're looking for someone who:

Uses AI as a force multiplier rather than a shortcut.
Independently solves unfamiliar problems.
Verifies information before trusting it.
Pays exceptional attention to detail.
Produces polished, professional work.
Communicates clearly and confidently.
Thinks critically.
Takes ownership.
Enjoys making complicated work feel organized.

What We Offer

You'll work directly with the founder of a growing business at the intersection of luxury real estate, artificial intelligence, publishing, and technology. We offer significant autonomy, direct access to decision-making, opportunities to build new systems, performance-based bonuses, and the chance to grow alongside a business that is expanding into new luxury markets across the United States.

If this assessment feels overwhelming, this role is probably not the right fit. If it feels exciting, we'd love to meet you.