Senior Technical Analyst, Engineering & Enablement (AI Solutions)

OUR COMPANY BACKGROUND \& CULTURE

UPP is the first pension plan of its kind in Ontario’s university sector, proudly serving over 46,000 members across six universities and nineteen sector organizations. Our purpose is to bring greater retirement peace of mind to the university sector by investing with integrity and serving members with care. As a sector-wide plan designed for growth, our doors are open to all Ontario universities.

UPP is recognized as one of Greater Toronto’s Top Employers for 2026. Together, we’re a team of progressive thinkers and agile doers operating within a fast-paced culture of collaboration and respect. We believe in bringing smart and capable people together to create, solve, and grow with a clear shared vision and values of integrity, inclusivity, ingenuity, and impact.

Our culture is intentionally welcoming and purposefully rooted in equity, diversity, inclusion, and reconciliation (EDI\&R). We believe diverse teams, perspectives, and lived experiences contribute to better decisions and a better workplace.

As a pension plan, UPP approaches investing through a long-term lens to generate and safeguard value. Our commitment to investing responsibly accounts for material risks that impact our investment portfolio to generate sufficient risk-adjusted returns to meet the pension needs of our members.

Join us in building a bright future for our members, our organization, and each other.

THE ROLE

We are seeking a Senior Technical Analyst, Engineering and Enablement, to help build, support, and continuously improve the technology solutions that enable UPP across our Corporate, Investments, and Pensions business pillars. This is a generalist technical analyst role with a strong focus on identifying, delivering, and operationalizing AI-enabled and automation solutions that drive efficiency, unlock innovation, and increase adoption of modern tools across the organization. The ideal candidate can translate high-level business needs and AI opportunities into clear functional specifications, user experience and workflow designs, implementation specifications, system requirements, solution designs, and adoption plans.

Reporting to the Director, Engineering \& Enablement, the individual will be a key member of the team, working closely with Solution Architects, cybersecurity, data and integration partners, business stakeholders, and key technology vendors to collaboratively shape, deliver, and support practical solutions. You will be comfortable moving between AI solution delivery, workflow automation, SaaS configuration, application support, requirements documentation, testing, and change enablement. You will bring a continuous learning mindset, a pragmatic approach to responsible AI, and a hands-on ability to turn ideas into secure, supportable, and adopted solutions.

This is a fantastic opportunity for a motivated individual who is excited by AI and emerging technology, while also being energized by the broad, hands-on responsibilities of a generalist technology analyst role. You will help UPP experiment responsibly, deliver useful solutions, support day-to-day technology needs, and make a measurable impact for our members, business partners, and employees.

This role is based in downtown Toronto under a hybrid work policy, allowing employees the flexibility to work remotely and in-office (approximately two days per week in-office).

KEY ACCOUNTABILITIES

In this role, you will execute with oversight from experienced peers on more complex items, while taking ownership of defined analysis, configuration, support, AI enablement, automation, and adoption deliverables.

• Provide Level 2 functional support for the assigned portfolio of applications and enabling platforms (e.g., IntraLinks, the Pension platform suite, NetSuite, Dynamo, Bloomberg, SharePoint tools, corporate SaaS platforms, Microsoft 365, low-code/no-code tools), resolving incidents and service requests in a timely manner.
• Triage production issues across front-, middle-, and back-office functions, perform initial impact analysis, and escalate to senior team members, developers, security teams, or third-party vendors as needed.
• Partner with business stakeholders to identify, assess, and prioritize AI, automation, and productivity improvement opportunities that can reduce manual effort, improve decision support, enhance employee experience, or increase adoption of existing platforms.
• Translate business and operational needs into clear documentation, including tickets, user stories, process maps, functional specifications, prompts or interaction flows, configuration specifications, data requirements, acceptance criteria, and adoption considerations.
• Support the design, configuration, testing, and rollout of AI-enabled and automation solutions using approved platforms and patterns, such as Microsoft 365/Copilot capabilities, SharePoint, Power Platform, workflow tools, enterprise SaaS platforms, cloud services, and knowledge-grounded assistants.
• Work closely with Solution Architects and senior L2 team members to ensure AI, automation, application, and integration changes align with UPP architecture, design standards, roadmaps, support models, and enterprise control requirements.
• Implement approved configuration changes and minor enhancements across supported applications and enabling platforms (e.g., GCP, OutSystems, SharePoint, the Pension platform suite, Atlassian, Oracle NetSuite, Microsoft 365, and approved AI/automation tools) to better support business needs.
• Apply UPP SDLC and delivery practices consistently, including requirements capture, documentation, testing, change management, controlled deployments, operational readiness, and post-release support.
• Ensure that application, data, integration, and AI-enabled changes comply with security, privacy, regulatory, data protection, records management, and responsible AI requirements; collaborate with cybersecurity, risk, legal, and data teams to implement and maintain required controls.
• Conduct functional testing, regression testing, user acceptance testing support, prompt/configuration validation, data quality checks, and output review to confirm that solutions are accurate, safe, usable, and fit for purpose.
• Support adoption and change enablement for new or enhanced solutions by preparing user guidance, demos, release notes, training materials, feedback channels, and communications that help employees understand and confidently use new capabilities.
• Monitor incidents, requests, adoption indicators, and solution performance metrics for supported systems and AI/automation use cases; identify recurring issues, measure benefits, and recommend process or system improvements for operational excellence.
• Maintain accurate support and solution documentation, including runbooks, configuration details, integrations, knowledge sources, decision logs, controls, best practices, user support procedures, and operational ownership information.
• Educate and support end-users and business stakeholders on system capabilities, new features, AI-enabled functionality, automation opportunities, and best practices to maximize value from tools such as SharePoint solutions, JIRA, Monday.com, CRM/marketing platforms, Microsoft 365, and other corporate applications.
• Liaise with third-party vendors (e.g., IntraLinks, TalkDesk, SAP, Salesforce, AI/automation vendors, and other SaaS providers) for incident escalation, enhancement requests, product capability assessments, roadmap awareness, and adherence to SLAs.
• Coordinate and communicate upcoming changes, releases, and maintenance windows across impacted business areas, ensuring clear expectations, stakeholder readiness, and adoption support.
• Assist project and change initiatives involving supported applications (e.g., new implementations, data conversions, workflow automation, AI-enabled productivity solutions, integration changes), including testing support and post-rollout stabilization.
• Contribute to the assessment of technology and AI-related risks within the assigned application portfolio, documenting risks, key decisions, business dates, stakeholder impacts, and mitigation activities.
• Support consistent solution review practices for new or enhanced vendor solutions to ensure they meet functional, non-functional, data, security, privacy, supportability, and adoption requirements.
• Maintain an up-to-date view of the supported portfolio (applications, enabling platforms, AI/automation use cases, key stakeholders, integrations, dependencies, and support ownership) and keep records current as ownership or scope evolves.
• Stay current with relevant technology and industry trends (e.g., generative AI, responsible AI practices, cloud platforms, SaaS tools, automation, collaboration tools, CRM tools, low-code/no-code platforms) and bring forward practical ideas for innovation and continuous improvement.
• Provide occasional support outside of core business hours for critical incidents, system releases, planned maintenance, or urgent stabilization activities affecting the supported applications or AI/automation solutions.

QUALIFICATIONS \& EXPERIENCE

• University degree or equivalent in Engineering, Computer Science, Information Systems, Data/Analytics, or a related field, and/or a comparable combination of education and relevant experience.
• 2-5 years of experience in technical analysis, system administration, application support, business systems analysis, automation delivery, or a related technology role.
• Experience supporting or delivering AI-enabled, automation, analytics, low-code/no-code, or productivity solutions; practical exposure to generative AI tools, prompt design, Copilot-style experiences, chatbots, document intelligence, or knowledge-based assistants is an asset.
• Solid understanding of core IT concepts such as application design, documentation, databases, user interfaces, business rules, APIs/integrations, workflow design, testing, support models, and release/change practices.
• Ability to gather and clarify requirements, translate ambiguous business needs into structured deliverables, and balance user experience, technical feasibility, security, privacy, operational support, and adoption outcomes.
• Hands-on experience with software testing (e.g., executing test cases, validating fixes, regression testing, UAT support, data validation, and reviewing AI/automation outputs for quality and usability).
• Experience working with cloud, collaboration, and productivity technologies such as Microsoft 365, SharePoint, Teams, and low-code/no-code tools (e.g., Power Apps, Power Automate, Copilot Studio, or similar platforms).
• Practical experience with SQL (e.g., querying data, basic joins, filters) for troubleshooting, reporting, data validation, or solution analysis activities.
• Experience with one or more enterprise SaaS platforms such as CRM, HCM, ERP, service management, workflow, or collaboration tools (e.g., Salesforce, Ceridian Dayforce, NetSuite, ServiceNow, Monday.com, or similar) is preferred.
• Awareness of cybersecurity, privacy, data governance, records management, regulatory, and responsible AI considerations as they apply to enterprise technology solutions.
• Strong analytical, documentation, stakeholder engagement, and communication skills, including the ability to coordinate with business stakeholders, vendors, technical teams, and change partners to resolve incidents or implement improvements.

NICE-TO-HAVE

• Experience with GCP, ChatGPT, Copilot, Claude, Gemini, or comparable cloud/AI enablement platforms.
• Exposure to financial services, pensions, or investment operations (e.g., understanding of core financial instruments or transaction/operations workflows).
• Experience supporting adoption of new technology, including user enablement, training, communications, change impact assessment, and benefits tracking.
• Exposure to Agile delivery, product ownership practices, service management, vendor management, or process improvement methodologies.

ATTRIBUTES

• Excellent written and verbal communication, with the ability to explain technical and AI concepts clearly to business and technology audiences.
• Curiosity and enthusiasm for emerging technologies, paired with pragmatic judgment about what is useful, secure, supportable, and adoption-ready.
• Ability to design and execute repeatable, efficient, maintainable, and measurable processes.
• Ability to organize work, manage competing priorities, and drive results through different contributors.
• Ability to engage and align users, partners, vendors, and technology teams to reach consensus and deliver outcomes.
• Comfort working across both innovative AI/automation initiatives and traditional technical analyst deliverables such as support, documentation, testing, configuration, and vendor coordination.
• Ability to identify emerging technologies, trends, standards, and products that have strong potential to better enable UPP business units while respecting risk, security, privacy, and operating model considerations.
• Continuous learning mindset and willingness to experiment, iterate, seek feedback, and help colleagues adopt new ways of working.

EXPECTED COMPENSATION

The expected compensation for this role is an annualized base salary in the range of $70,800 to $95,800. This range reflects the expected range for new hire base salaries and is subject to change and may be modified in the future.

You may also be eligible for a variable incentive depending on organizational, divisional and personal performance. The final total compensation offered will vary depending on your skills, experience and other factors.

LIFE AT UPP

Do work that matters. We are duty-bound to serve our members’ interests, and it’s a responsibility we don’t take lightly. That’s why we’ve ingrained sustainability in our work from day one—to ensure our members have a resilient future to retire into, both today and for generations to come.

Stronger together. Collaboration is how UPP was born, and it’s how we work with each other and our partners day in, day out. No one at UPP is just a number (even if they are excellent at math) and every win is a shared win.

Grow every day. You’ll have the opportunity to work on unique, once-in-a-career projects that maximize your skill set and probably teach you some new ones—at any stage in your career.

Prioritize wellness. At UPP, wellness takes many forms. Ultimately, it’s about ensuring our people are cared for in the ways that matter to them. Check out some highlights of our inclusive employee-focused benefits program including:

• Defined benefit pension plan
• Flexible hybrid work model
• Paid time off – vacations, personal days and wellness days
• Work remotely up to eight weeks/year
• Comprehensive group benefits including medical, dental, vision, etc.
• Extended paramedical and mental health service coverage
• Health care and lifestyle spending accounts
• Fertility treatments, paid parental leave, and gender affirmation coverage
• Education Assistance program

This posting will remain open for a minimum of seven (7) days and will remain open until a sufficient number of qualified applications are received or finalist candidates have been identified.

Artificial intelligence (AI) tools may be used to support certain stages of the recruitment process, including sourcing, screening, and assessment. All hiring decisions involve human review and intervention by UPP employees.

UPP enthusiastically welcomes applications from all qualified applicants and especially invites people with lived experience as an Indigenous person, a person with a disability or as a member of another Human Rights Code protected group that faces barriers to employment to apply. Our goal is to create a barrier-free experience for every candidate throughout the recruitment process.

UPP respects your privacy. For information on how UPP handles the personal information you provide during the application process, please see our Job Applicant Privacy Statement.