Director of Real Estate Investments

Job Title: Director of Real Estate Investments

Company: Watson Companies

Location: Bend, OR

Career Area: Finance, Asset Management

Education: Bachelor’s degree in Finance, Accounting, Business, or related field, with advanced credentials (MBA, CFA, CPA, or equivalent graduate-level qualification)

Experience: 15 years progressive experience in real estate development, investment, asset management, and leadership roles.

Travel: Generally 1 day / week and multiple days / month

We are proud to be Great Place to Work Certified® and selected as a Fortune 100 Best Workplaces!

How You Will Contribute

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.

Responsibilities

• Team and Office Leadership: 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.
• Financial and Operational Leadership: 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.
• Real Estate and Fund Oversight: 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.
• Cash Management and Capital Strategy: 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.

How You Will Succeed

Success in this role comes from the ability to think strategically while exercising strong financial judgment and disciplined capital allocation. The individual will effectively coach and develop others, fostering accountability and high performance across the team. By combining deep financial acumen and underwriting expertise with the ability to identify and mitigate risk, this leader will make sound, timely decisions that support long‑term objectives. Strong executive‑level communication and relationship management skills will also be essential, enabling the individual to build trust, align stakeholders, and maintain productive partnerships with the family, team members, and external partners.

What You Can Offer

• Education — Bachelor’s degree in Finance, Accounting, Business, or related field, with advanced credentials (MBA, CFA, CPA, or equivalent graduate level qualification).
• Skills — 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.
• Abilities — 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.
• Experience — 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.

How You Will Be Rewarded

Watson Companies compensation and benefits package consists of a 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, and volunteer time off.

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