Senior Analyst, Investment Analytics & AI Automation

Hillsdale Investment Management Inc. is expanding and is excited to offer an opportunity to join our Institutional Investment Services Team (IIS) as a Senior Analyst, Investment Analytics & AI Automation. Reporting to the Senior Manager, Institutional Deliverables, the successful candidate will play a hands-on role in designing, developing, and maintaining automation and data solutions that enhance the speed, scalability, and quality of Hillsdale’s institutional investment workflows and client deliverables. The role serves as a key link between the investment team, engineering team, and institutional client services team.

The IIS Team is responsible for creating investment content and institutional deliverables to serve clients and support new business development. Through a solutions-oriented approach, the Team customizes communications to the unique needs of clients and prospects, while partnering closely with the Portfolio Management, Investment Research, and Data Engineering teams.

This role requires you to develop a strong understanding of Hillsdale’s Body of Knowledge, including our investment philosophy, strategies, research methodologies, and institutional client requirements, through reviewing investment presentations and written content and participating in relevant Portfolio Management and Investment Research meetings.

Your key responsibilities will include:

• Python and Automation Expertise: Serve as the IIS Team’s Lead Python and Automation Specialist and subject matter expert for automation, collaborating with Hillsdale’s engineering teams and providing technical expertise to advance the Team’s automation capabilities.
• Solution Development: Identify opportunities for automation and design, develop, and maintain automation and data solutions for recurring IIS workflows and institutional client deliverables, using Python, SQL, and other appropriate technologies.
• AI Agents and Intelligent Automation: Design, develop, and implement AI-powered agents and workflows that automate complex, multi-step IIS processes, integrating AI capabilities with Python, internal data sources, and existing automation tools.
• End-to-End Ownership: Take ownership of solutions from requirements gathering and design through development, testing, implementation, documentation, and ongoing maintenance.
• Institutional Deliverable Automation: Automate the production of presentations, reports, questionnaires, and exhibits, including data retrieval, calculations, tables, charts, and other client-ready outputs.
• Scalability and Efficiency: Enhance and standardize automation tools and data workflows to improve operational efficiency, reliability, and scalability across Hillsdale's growing platform of investment strategies, mandates, and clients.
• Teamwork and Knowledge Sharing: Collaborate with IIS colleagues, share technical expertise, provide guidance on automation tools, and contribute to a culture of collegiality and continuous learning.
• Ensure that all client communications are aligned with the principles of excellence embedded in Hillsdale’s Best Practices.
• Contribute more broadly to the enhancement and production of Hillsdale’s institutional investment solutions and client deliverables.

WHAT WILL YOU BRING?

This role requires strong hands-on Python development and automation capability, combined with analytical problem-solving skills and the ability to work effectively with investment and portfolio data and a foundation in quantitative investing and statistical analysis. You are intellectually curious, proactive, and committed to continuous learning, with a demonstrated ability to incorporate feedback and guidance effectively. Your qualifications include:

• 3 to 5 years of hands-on development experience, with demonstrated experience in building, debugging, validating, and maintaining reusable, scalable automation tools and data workflows.
• Strong practical experience with Python, Pandas, and structured datasets, together with SQL, APIs, ETL/data pipelines, or similar data-integration workflows. Strong software discipline, including developing, testing, error/exception handling, documentation, Git version control, and code reviews.
• Demonstrated hands-on experience designing and deploying AI agents and agentic workflows to automate complex business processes.
• Excellent analytical and problem-solving skills and the ability to independently troubleshoot complex workflow and data issues.
• Experience developing and maintaining automated workflows for PowerPoint presentations, Excel-based analysis, recurring reports, and document production, including data integration, formatting, and quality control.
• Ability to communicate technical concepts clearly and work effectively with both technical and non-technical colleagues.
• A proactive, self-starting mindset with an interest in identifying opportunities for automation and developing robust solutions.
• Experience working with investment, portfolio, or financial data within a quantitative/systematic investment manager, asset manager, pension fund, investment consultant, bank, or similar financial institution is an asset.
• A degree in Computer Science, Engineering, Mathematics, Statistics, Finance, or a related quantitative discipline, or equivalent relevant experience.
• CFA charterholder or actively pursuing the CFA designation is an asset.
• Bilingualism (English/French) is an asset.
• Must be legally entitled to work in Canada.

WHAT’S IN IT FOR YOU?

• Competitive base salary plus generous performance-based bonus, retirement savings matching and Health Care Spending Account. Actual compensation will vary based on several factors, including bonus eligibility, relevant experience, skills, education/training, and location. The upper end of the range is typically reserved for candidates who demonstrate expertise exceeding the position’s requirements.
• Paid time off - vacation, study, and volunteer.
• Ongoing professional development, mentorship, and a clearly defined career path.
• The opportunity to learn from and collaborate with leading professionals in quantitative investing, research, and technology.
• A flexible work environment with commuting reimbursement for days spent in the office.
• Gym membership and ergonomic workstations to support your health and well-being.
• An employee charitable giving program that matches donations and supports volunteer initiatives.
• Access to an in-house Personal Financial Advisor.
• A centrally located office at King and Bay features free lunches, a fully stocked kitchen, and panoramic views of Toronto and Lake Ontario.
• A high-performance, knowledge-driven culture focused on continuous learning, collaboration, and investment excellence.

ABOUT HILLSDALE

Hillsdale Investment Management Inc. (Hillsdale) is an independent, employee-controlled, and client-aligned investment boutique managing investments on behalf of a select group of sophisticated institutional and private wealth investors. We specialize in designing and successfully implementing systematic, bespoke investment strategies across a diverse set of objectives including high alpha, ESG, customized and smart beta. Hillsdale is recognized for both investment and service excellence – a reflection of our relentless pursuit of research and development and the dedication of our employees who invest alongside our clients.

Hillsdale has been recognized as a Great Place to Work for our industry and across Canada.

APPLICATION DEADLINE: November 30, 2026.

Additional Information:

This job advertisement is a current vacancy for a new opportunity. Hillsdale may use artificial intelligence (AI) tools to assist in screening and assessing applicants. The use of AI does not replace human decision making.

Hillsdale is an equal opportunity employer and as such does not discriminate based on race, colour, religion, sex, national origins, age, sexual orientation, disability or any other characteristic protected by applicable laws. We encourage applications from people of all abilities and will make reasonable accommodations upon request.

Not sure if you qualify? Apply anyway! Our workforce comes from diverse backgrounds and industries. Please forward a resume to careers@hillsdaleinv.com.

We thank all interested applicants, however, only those selected for an interview will be contacted.

Download the full job posting in PDF