Senior Analyst, Investment Analytics & AI Automation

Hillsdale Investment Management Inc. is expanding and is excited to offer an prospect 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 clearl

📌 Senior Analyst, Investment Analytics and AI Automation (Toronto)
🏢 Hillsdale Investment Management
📍 Toronto