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Director of AI Initiatives

Type: Permanent
Compensation: $500k - $600k / year
Location: Chicago, Illinois (Onsite)

Total compensation is expected to be in the range of $500,000 to $600,000, including base salary and annual bonus, commensurate with experience and anticipated contribution.


Director of AI Initiatives - Investment Management


Position Overview:

Our client is a well-established investment manager with several billion dollars in assets under management, serving institutional investors and family offices. The firm runs a focused set of fundamental investment strategies with a lean team of investment professionals and a small operations and technology group, and has built a strong long-term track record.


The firm is seeking a Director of AI Initiatives to lead its first dedicated AI effort. Reporting to the Chief Operating Officer, with a direct working relationship with the Founder/CIO and the investment team, this individual will define how the firm uses AI across its investment process and operations, and will personally build and deploy the tools that make it happen. This is a newly created, high-impact role for a hands-on leader who wants to shape the function from the ground up.


While the role does not carry a C-level title, it holds a meaningful seat at the table. The Director of AI Initiatives will be part of the firm's senior leadership group, participate in strategic planning and budget discussions, present directly to the firm's founders, and work as a peer alongside the COO, CFO, and CCO on decisions that shape how the firm operates and invests.


The ideal candidate combines strong technical skills in modern AI with an understanding of how investment teams work, and is equally comfortable setting strategy, writing code, and sitting with portfolio managers to solve real problems.


Responsibilities will include (but not be limited to):

  • Develop and own the firm's AI strategy as a member of the senior leadership group, working with the COO and Founder/CIO to identify where AI can most improve investment research, decision making, and day-to-day operations, and setting a practical, prioritized roadmap.
  • Serve as a hands-on builder, personally designing, prototyping, and deploying AI tools and agents rather than overseeing a large team, with support from a small group of engineers and data professionals as the function grows.
  • Work side by side with portfolio managers and analysts to build AI research assistants that summarize filings, earnings calls, broker research, and news, track positions and catalysts, and speed up idea generation and due diligence.
  • Evaluate and select AI vendors, platforms, and model providers, favoring proven enterprise tools where they fit and building in-house only where it creates a real edge for the firm, while managing costs carefully.
  • Test AI tools for accuracy and reliability on the firm's own data before they are relied upon by the investment team, and set simple, repeatable standards for evaluating new models and products.
  • Partner with the firm's technology lead and outsourced IT and data providers to make sure data, systems, and security can support AI tools, including connecting internal research, market data, and document repositories.
  • Work with the CCO and outside counsel to establish practical AI policies covering acceptable use, data privacy, MNPI and information barrier controls, vendor due diligence, recordkeeping, and investor and regulatory disclosures.
  • Bring AI into non-investment functions such as operations, accounting, investor relations, and compliance to automate manual work and allow a lean team to scale without proportional headcount growth.
  • Train and support employees across the firm on effective, responsible use of AI tools, and drive adoption through hands-on help rather than mandates.
  • Track and report the impact of AI initiatives to the COO, the founders, and the senior leadership group, including time saved, adoption, and contribution to the investment process, and help explain the firm's AI capabilities to investors and in operational due diligence.


Qualifications:

  • 10+ years of experience in machine learning, data science, or software engineering, including recent hands-on work building and deploying applications using large language models.
  • Practical experience with LLM APIs, agent frameworks, retrieval systems (RAG), prompt design, and model evaluation, with the ability to code (Python strongly preferred) and ship working tools quickly.
  • Experience in financial services, ideally at a hedge fund, asset manager, or trading firm, with a solid understanding of how investment teams research and make decisions.
  • Comfortable operating as a team of one or a small team in an entrepreneurial environment, balancing strategy with hands-on execution.
  • Sound judgment on build-versus-buy decisions and experience managing vendors and budgets.
  • Working knowledge of data security, privacy, and compliance considerations at a regulated investment firm.
  • Bachelor's degree in Computer Science, Engineering, Mathematics, or a related field; advanced degree a plus.
  • Clear communicator who can explain technology in plain terms, earn the trust of portfolio managers, and drive adoption across a small, high-performing team.



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