Willow Wealth Inc.
Fintech & PaymentsDirect Rippling career site

Managing Director, Head of Direct Investments

Pay
$250,000 – $300,000 per year
Location
New York, NY · On-site
Job type
Full-time
Level
Director
Experience
12+ years
Listed
31 days ago

Skills & highlights for this role

  • private credit
  • private market investment structuring
  • investment underwriting

Also useful

  • private equity
  • venture capital
  • real estate investing

Stated benefits & perks

  • Health
  • Dental
  • Vision
  • 401k match
  • Unlimited pto

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

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.
  • About Company ---

About t he 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.

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.

Read the original posting

From Willow Wealth Inc.'s careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.

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Common questions

What is the salary for the Managing Director, Head of Direct Investments role at Willow Wealth Inc.?

The Managing Director, Head of Direct Investments posting at Willow Wealth Inc. states compensation of $250,000 – $300,000 per year. It is listed as a full-time position. Final pay may depend on location, experience, and interview evaluation on Willow Wealth Inc.'s official career site.

Where is the Managing Director, Head of Direct Investments job at Willow Wealth Inc. located?

This Managing Director, Head of Direct Investments position at Willow Wealth Inc. is located in New York, NY (On-site). Always check Willow Wealth Inc.'s application page for specific state eligibility or relocation policies.

What qualifications are required for Managing Director, Head of Direct Investments at Willow Wealth Inc.?

For the Managing Director, Head of Direct Investments role, Willow Wealth Inc. highlights 12+ years of relevant experience; experience with private credit, private market investment structuring, investment underwriting. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Managing Director, Head of Direct Investments position at Willow Wealth Inc.?

This listing links directly to Willow Wealth Inc.'s Rippling application page. You can apply directly on Willow Wealth Inc.'s site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Rippling application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.