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Debt Capital Markets - VP of Commercial Real Estate (Remote)

March 7, 2026

Debt Capital Markets - VP of Commercial Real Estate (Remote) Hey there! We’re Gumption, a fast-growing startup that’s changing the game in commercial real estate (CRE) financing. Gumption is a platform built by CRE owners for CRE owners. We leverage deep lender relationships and AI to deliver best-in-market financing terms. We’re at the intersection of finance, real estate, and technology, and you’ll gain experience in all 3 while helping us shape the future of this massive industry. About the role: We’re looking for someone who is relentless and entrepreneurial with at least 3 years of hands-on experience in commercial real estate capital markets. You’ll connect with professionals across the CRE landscape like property owners, funds, family offices, banks, debt funds, insurco’s, agency lenders, etc. You should be comfortable with financial analysis, deal execution, and working directly with clients. In this role, you’ll get to dive into complex real estate deals—everything from debt placement to advisory work across a variety of asset types.This is an ideal role for someone who is enthusiastic, coachable, and eager to grow within a high-performance sales environment. This role will be remote at first with the option of joining or starting an office in certain locations. What you’ll be doing: • Source and close financing transactions: Originate, structure, underwrite, and execute debt transactions for commercial real estate assets, evaluating new opportunities and engaging directly with sponsors, borrowers, lenders, and internal business lines. • Own market production: Manage inbound leads and proactively reach out to potential clients through calls, emails, and social media to introduce them to our platform. Build relationships with CRE professionals in your region and consistently drive toward production goals. • Lead financial analysis: Review and interpret financial models, including cash flow projections, debt sizing, sensitivity analyses, and valuations based on historical data, borrower models, and market benchmarks. • Prepare investment materials: Draft and refine investment memoranda, lender packages, and client presentations with clarity, accuracy, and a polished presentation style. • Conduct market research: Monitor capital markets trends, lender activity, and real estate fundamentals to inform strategy and support business decisions. • Optimize client/partner experiences: Coordinate with lenders, borrowers, legal teams, and internal stakeholders throughout each transaction, assisting with due diligence and documentation. • Leverage our technology: Use the Gumption platform, proprietary AI tools, CRM systems, and transaction databases to maintain data accuracy and ensure timely reporting. What we’re looking for: • We want self starters and future entrepreneurs with a growth mindset and relentless drive. You can own a market/region for Gumption and hit production goals. • At least 3 years of hands-on experience in commercial real estate finance, investment banking, or debt capital markets. • Bachelor’s degree in real estate, finance, accounting, or a related field preferred; a master’s degree or professional certification is a plus. • Strong skills in financial modeling, underwriting, and deal execution, with a solid grasp of valuation methods and the ability to translate complex analysis into clear investment insights. Comfortable working with cash flow metrics like NOI, DSC, ROC, and IRR. • Excellent at managing multiple projects while communicating clearly and confidently. Able to present financial insights and investment strategies effectively to senior leaders and external partners. • Skilled at building strong relationships—both internally and externally. Resourceful, collaborative, and always acting with integrity. Why Gumption? • Our Culture: Zero corporate fluff here. We’re a startup, and we keep things casual and transparent. We’re results-focused and relentlessly determined–not your typical 9-to-5 crew. If you’re looking for a place to make an impact, this is it. • Office Environment: We work out of the Brickyard in Chattanooga, TN where we have a gym, sauna, and cold plunge right next to the office to keep employees healthy and energized. The Birmingham office is downtown in a remodeled industrial warehouse decked out with good vibes and a golf simulator to keep your game polished. • Compensation: Competitive base salary + commission structure. Your success directly impacts your earnings—there’s no cap on what you can make. • Health Coverage: Comprehensive medical benefits Ready to learn, grow, and help shape Gumption’s success? We’re excited to meet you! Recruiting inbox: careers@gumption.dev Gumption is proud to be an equal opportunity employer. We welcome candidates of all backgrounds and experiences and are committed to building a diverse, inclusive workplace. Apply tot his job

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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?

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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...

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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...

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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...