Managing Director, Head of Direct Investments

About Willow Wealth Willow Wealth is a leading platform for private market investing, connecting individual investors with curated opportunities across real estate, private credit, private equity, and more. Founded in 2015, the platform has grown to serve more than 500,000 members with $6.9B+ invested since inception. The company has raised over $250M from leading institutional investors, such as Redbird, Tarsadia, Mayfair, StepStone, and Edison Partners.

About the Role Willow Wealth is seeking a Managing Director, Head of Direct Investments to lead our direct investing strategy across private credit, real estate and private equity. This role will serve as a counterpart to our Managing Director, Head of Fund Investments. This individual will report directly to the CIO and serve as a key member of the investments team. The Head of Direct Investments is a strategic hire at this moment in our company’s scaling journey and will be responsible for setting long-term investment vision and driving new originations in direct investments. Additionally, given Willow Wealth’s retail orientation, the Head of Direct Investments will play a critical role in earning investor trust through consistent performance, clear communication, and ongoing education.

Willow Wealth is undergoing a strategic evolution to becoming a marketplace for retail investors to locate and evaluate private investments across the risk spectrum. This role will be instrumental in populating the marketplace through sourcing, evaluating, and closing direct deals. This requires forging and deepening relationships with top-tier managers, identifying and structuring differentiated investment opportunities and ensuring the platform delivers on both performance and accessibility for Willow Wealth’s retail investor base. The Head of Direct Investments will additionally be tasked with managing both internal and sub-advisory teams in connection with the ongoing management of Willow Wealth’s existing portfolio of assets.

Key Responsibilities The Head of Direct Investments will be responsible for leading and shaping Willow Wealth’s direct investment strategy and execution across private market assets. Core responsibilities include:

• Investment Strategy & Leadership

• • Develop and execute a plan to bring direct deals to the platform across asset classes

• Participate in the firm’s investment committee and help evaluate its tactical investment decisions

• Partner with the CIO, CEO, President, CFO and others to align investments with company and investor goals

• Represent the firm externally with investors and industry partners

• Sourcing, Underwriting and Execution

• • Foster deep relationships with best-in-class asset managers to source investment opportunities for the platform

• Lead due diligence, structuring and evaluation of new investment opportunities

• Drive the execution of investment ideas into offerings on the platform, partnering with internal teams through the investment committee process

• Portfolio Management & Asset Allocation

• • Oversee direct deal allocation and portfolio construction

• Manage sub-advisory relationships relating to Willow Wealth’s existing portfolio of private credit and specialty finance assets

Qualifications The ideal candidate possesses 12-15 years’ experience in investment management, in increasingly senior roles with a demonstrable track record of delivering investment impact. Deep familiarity across all asset classes, with an emphasis on credit, is essential, along with the ability to navigate the complexities of investment structuring and execution. The candidate must bring strong private market knowledge and an extensive network to source high-quality opportunities for Willow Wealth’s portfolio. This role may present a step-up opportunity, offering the chance to shape a portion of the investment vision of a scaling platform and play a pivotal role in democratizing access to private markets for a rapidly growing investor base.

• The ideal candidate possesses 12-15 years’ experience in investment management, including at least five years in a leadership role
• Deep familiarity and connectivity with private market investment managers is essential, along with the ability to navigate the complexities of investment structuring and execution
• Strong private market knowledge to source high-quality managers across private equity, private credit, and venture capital while maintaining robust sourcing pipelines is critical
• A degree from a recognized university or institution of higher education is required
• An MBA, CFA, or equivalent experience is highly preferred

What's in it for you Competitive compensation package, including equity Health, dental & vision coverage with FSA/HSA options Unlimited PTO 401k match Commuter benefit Life insurance Wellness stipend

This is a New York-based role. The base salary range for this position is USD 250,000 to 300,000 annually, depending on experience and qualifications. This role is eligible for a discretionary bonus and equity compensation as part of the total compensation package.