Director of Real Estate Investments

Hayden Homes LLC • Bend, OR

21h • $160,000

About The Position

The Director of Real Estate Investments will play a critical role in advancing the long-term vision and success of the Watson Companies family office by aligning financial stewardship with strategic execution. As an executive leader, this position will translate the family’s long-term objectives into actionable plans that guide capital allocation, asset performance, and operational systems. With disciplined financial oversight and cross-functional collaboration, the Director of Real Estate Investments will help ensure the organization operates efficiently while pursuing sustainable growth.

Requirements

• Bachelor’s degree in Finance, Accounting, Business, or related field, with advanced credentials (MBA, CFA, CPA, or equivalent graduate level qualification).
• Excellent verbal and written communication skills
• Proficient in Microsoft Office Suite; strong skills in Excel building complex spreadsheets and formulas
• Highly organized with strong attention to detail and ability to manage multiple projects simultaneously
• Strong leadership and interpersonal skills, including high emotional intelligence, sound judgment, and the ability to navigate sensitive and confidential matters
• Ability to build strong relationships with lenders and partners
• Ability to model high emotional intelligence, strong communication, and trust building with team members, partners, and the family.
• Demonstrated ability to build and improve systems in a lean, entrepreneurial environment
• Ability to travel a few days per month or as needed throughout Pacific Northwest
• 15+ years progressive experience in real estate development, investment, asset management, and leadership roles
• Proven record of leading teams or platforms and owning portfolio, P&L, or enterprise-level operational outcomes
• Deep experience with forecasting, financing, and capital deployment across complex structures

Responsibilities

• Provides leadership and oversight for the family office team, ensuring roles, priorities, and expectations are clearly aligned.
• Cultivates and fosters a culture that is curious, creative, intentional, and growth-oriented.
• Ensures day-to-day office operations run smoothly and support the broader mission and values of Watson Companies.
• Owns overall financial and operational performance of the family office.
• Serves on the leadership team, shaping strategy, priorities, and execution.
• Designs and refines operating models, processes, and reporting that support scale, transparency, and accountability.
• Provides strategic oversight of real estate asset and property management activities.
• Oversees land bank fund operations and reporting, including capital calls, distributions, liquidity planning, and risk management.
• Advises and participates in major asset and fund level strategies and recommendations.
• Ensures performance information is accurate, timely, and decision ready.
• Leads forecasting for cash flows, capital needs, and distributions across entities and assets.
• Oversees closings, fundings, and capital deployment in line with risk/return targets and long-term goals.
• Manages relationships with lenders, banking partners, and other capital providers.
• Coordinates with accounting, tax, and financial advisors on capital structure, tax efficiency, and long-range planning.

Benefits

• competitive base salary, estimated total starting at $160,000 + / year, along with bonus opportunities
• generous health care coverage including medical, dental and vision benefits for team members and dependents
• flexible spending accounts
• life and disability insurance
• 401(k) plan with a generous company match
• a team member home purchase discount
• paid time off
• volunteer time off

What This Job Offers

• Job Type: Full-time
• Career Level: Director