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Sr. Real Estate Underwriting Analyst at SIP Ventures - US-based early-stage residential real estate development and investment firm (remote)

May 15, 2026

Location: Remote

Reports to: Principal / Investment Lead

SIP Ventures is a New York-based real estate development and investment firm executing high-conviction strategies within the residential real estate sector through programmatic joint ventures. The firm focuses on acquiring and developing townhome and multifamily communities across the Southeast and Northeast United States. With an active deal pipeline and a lean, technology-forward approach to underwriting and operations, SIP Ventures is building out a high-performance analytical team to scale with the business.
Role Overview

The Sr. Real Estate Underwriting Analyst supports SIP Ventures' development and acquisitions platform through financial underwriting, deal analysis, market research, and investor communications.

This is a thinking-oriented, execution-focused role. The right person does not just plug numbers into models — they understand what the numbers mean, catch errors before they matter, and communicate findings clearly to partners.

This is not a passive data-entry position. Success is measured by analytical judgment, output quality, and the ability to operate with increasing independence.

Core Responsibilities

Underwriting & Financial Modeling
Input deal assumptions into existing underwriting models and tailor them by geography and asset type
Validate outputs and proactively flag results that don't make sense
Stress-test assumptions and interpret return metrics in context
Support deal flow processing across multiple active opportunities simultaneously

Market Research & Deal Analysis
Research market-level assumptions (rents, costs, comps, supply/demand dynamics) for each deal
Synthesize findings into clear, structured inputs for the underwriting model
Identify when assumptions are off-market and recommend adjustments

Investor Materials & Presentations
Translate underwriting outputs into concise investor memos and PowerPoint presentations
Prepare deal summaries for investor partners with clean visuals and clear narrative
Support longer-form presentation materials as needed

Workflow & Process Support
Maintain deal pipeline documentation and file organization
Leverage AI tools (e.g., Claude, ChatGPT) to accelerate research and drafting tasks
Contribute to improving internal workflows and analytical processes over time

Required Qualifications
3–5 years of experience in US commercial or residential real estate underwriting, acquisitions, or financial analysis
Strong Excel skills — advanced formulas, financial modeling, assumption-driven analysis
Ability to interpret model outputs, not just build or populate them
Strong written English — capable of drafting investor-facing memos and presentations
Solid research skills and comfort working with market data
High attention to detail and deadline discipline

Ideal Profile
Conceptually strong in real estate — understands the asset class, not just the spreadsheet
Analytical and intellectually curious — asks "does this make sense?" before submitting
Clear communicator in writing and presentation format
Comfortable working independently in a fast-moving, lean team environment
Bonus: familiarity with AI tools; technical or engineering background is a strong plus

Growth & Development

This is a foundational hire for a growing platform. As the analyst builds trust and demonstrates strong judgment, there is a clear path to taking on greater ownership across deal evaluation, investor communication, and process architecture — including contributing to SIP Ventures' evolving tech and workflow infrastructure.

High performers will have meaningful exposure to live transactions and direct access to senior decision-makers within an active programmatic JV platform.
Working Hours

Full-time role with preferred overlap with US Eastern Time business hours. Flexibility for the right candidate — partial overlap (at minimum) is required for real-time collaboration.
What We Offer
Full-time remote position (Monday–Friday, 8 hours/day)
Remote work from any city with reliable internet and ability to align with US Eastern Time
Direct exposure to live US residential real estate development and investment transactions
Opportunity to grow within a lean, high-performance team at an early stage — your work will be visible and impactful from day one

Application deadline: March 21, 2026.

Please note that the later you apply — the more intensive your selection process will be, for example, you will have less time for the test assignment, etc

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...