Job Details

About the role

At YouLand, our Chief of Staff is the operational right hand to the CEO. You'll run daily execution across capital markets, deal flow, and sales pipelines—so the CEO can focus on fundraising and long-term strategy. Think of this as a hybrid of COO, revenue operations lead, and systems integrator, embedded across the full real estate lending lifecycle.

What You'll Do

Daily Operational Rhythm

• Run and lead daily 9 AM deal syncs with sales, capital markets, and operations
• Know exactly:
  • How many loans we're closing today
  • How much capital is coming in and going out
  • Which deals are ready vs. stalled (and why)
• Keep everyone on track—from processors to capital partners

Pipeline & Deal Management

• Oversee all active borrower deals from origination → draw → payoff
• Assign deals to the right processor based on workload and experience
• Track documentation bottlenecks and help unblock team members quickly

Capital Market Alignment

• Coordinate with internal and external capital markets teams
• Understand which loans are being sold, at what price, and to whom
• Ensure cash liquidity aligns with funding timelines and draw approvals
• Partner with warehouse line providers and securitization partners

Cross-Functional Ops Oversight

• Act as central coordinator across loan processing, underwriting, and post-close servicing
• Track delinquencies and partner with our asset management team on resolution strategies
• Help manage bad debt workouts, note sales, or legal escalations when necessary

What We're Looking For

• You've operated at the center of chaos and built systems that create clarity
• You understand real estate lending or private credit (bonus: bridge loans, DSCR, fix-and-flip, or warehouse lines)
• You can lead standups at 9 AM, talk pricing with capital partners at 10 AM, and unblock a processor by 3 PM
• You bring high ownership, operational curiosity, and a bias toward execution
• You're humble, fast-learning, and thrive in a roll-up-your-sleeves environment

This Role Is Ideal If You…

• 2–4 years of experience in fast-paced, analytical environments (e.g., consulting, banking, venture, private credit, or startups)
• Are a former Chief of Staff, BizOps lead, or early-stage operator ready to own a company's heartbeat
• Want a front-row seat to how real estate lending, capital markets, and fundraising work together
• Aspire to grow into a COO or VP of Ops role in a high-growth startup
• Can speak the language of both strategy and execution, and care more about outcomes than slide decks

Additional Details

• Full-time, in-person (Menlo Park / Palo Alto)
• Competitive compensation package and benefits
• 4-year undergraduate degree required (3.5+ GPA preferred)