About the Event
There is a lot of discussion happening right now around how PMs should be using AI in their day-to-day jobs, but very little specifics around what we need to be thinking about when it comes to actually BUILDING AI products and features. What do Product Managers need to keep in mind as they evaluate opportunities, prioritize, start building and then test towards a release? This evening is going to give folks real insight into what actually happens on the pathway to releasing an AI feature. Three product leaders. Three keynotes. Three stages of building AI features—from strategy to shipped product.
This isn't a panel discussion. These are actionable presentations with real-world examples, live demos, and soup-to-nuts breakdowns of how AI gets built and shipped.
What You'll Learn
Stage 1: Strategy & Prioritization
Jenna Stavros, VP of Product at Dig Insights
How do you identify AI opportunities that actually matter? Jenna walks through the process of assessing AI use cases, aligning them to organizational strategy, and prioritizing based on real value. You'll learn how to select the right AI opportunity to drive forward—and avoid the noise.
Stage 2: Implementation
Sagar Giri, Product - Managed Services at Synacor
What does it take to go from use case idea to implemented concept? Sagar breaks down the fundamental architecture and infrastructure decisions that make or break AI delivery. This includes a live demo showing how AI features get built in practice. Sagar has shipped AI products to 220M+ users, built an AI clinical assistant for NHS, and processes 80M+ posts daily through content moderation infrastructure.
Stage 3: Testing & Validation
Matthew Tobiasz, General Partner & Co-Founder at Sightglass
How do you know your AI feature actually works? Matthew shares real examples of testing AI implementations soup-to-nuts to ensure they perform as required before reaching users. Learn the validation approaches that catch issues early and build confidence in your AI features.
Each speaker will define key terms, explain specific elements, and clarify what the product manager's role is in their stage of the process.
Meet Your Speakers
Jenna Stavros – VP of Product, Dig Insights
A customer-oriented product leader who thrives in problem-driven environments, Jenna brings empathy and curiosity to every challenge. She's passionate about supporting aspiring PMs and helping teams navigate complex product decisions.
Sagar Giri – Product, Managed Services, Synacor
With 15+ years of experience and 8 years focused specifically on Data and AI, Sagar builds AI products that ship and scale. He's hands-on with GenAI, RAG architectures, and ML infrastructure. His track record includes shipping an AI clinical assistant for NHS, building content moderation infrastructure processing 80M+ posts daily, and scaling conversational AI to 220M users.
Matthew Tobiasz – General Partner & Co-Founder, Sightglass
Matthew thrives at the intersection of technology, strategy, and product design. With a technical background as a software developer rooted in human-computer interaction, he spent his early career at ThoughtWorks leading delivery teams across industries—from financial services to biotech, from startups to Fortune 500s. He helps teams reimagine product capabilities into customer-focused experiences.
Who Should Attend
- Product managers exploring AI implementation
- Product leaders building AI roadmaps
- Founders and entrepreneurs integrating AI into their platforms
- Anyone moving from AI experimentation to production
Event Tickets
This event is open to everyone, but a free TPMA membership is required to attend.
Tickets cost $15 for regular TPMA Members and $11.50 for Community-Builder level members. Update your membership here.
Your ticket includes a drink and a selection of light snacks.
Event Agenda
5:30 – 6:00 PM — Networking (in-person only)
6:00 – 7:15PM — 3 x 20-minute keynote presentations with real world examples and demos + Q&A
7:15 – 8:00 PM — Networking with Toronto's product community
Location
In-person @ BrainStation - 482 Front St W 2nd floor, Toronto, ON & Online via Zoom.
Accessibility
For any accessibility concerns, please reach out to us at info@tpma.ca.
Read Speaker Bio
Jenna Stavros is a senior product leader with over a decade of experience in tech, focused on building and scaling B2B products through a deeply customer-led lens. After entering product via a non-traditional path in sales, she developed a sharp ability to translate real customer needs into products that drive meaningful business impact.
She has held product management roles across multiple B2B organizations and now leads the product and design teams at Dig Insights, where she drives the strategy and evolution of Dig One, the platform behind Upsiide and OneCliq.
Jenna is passionate about demystifying product leadership, mentoring emerging PMs, and helping the next generation of builders develop the skills needed to succeed in today’s product - led organizations
Read Speaker Bio
Sagar Giri is an AI Product Manager, Founder and Advisor passionate about building AI products that work at scale.
Over 6+ years leading Data and AI teams, he has shipped a clinically validated AI chatbot at Wysa serving 7M+ users globally and built an AI-powered brand safety platform serving Fortune 500 brands at Viral Nation. He holds a Master's in Computer Science, combining deep technical expertise with product strategy.
Sagar specializes in guiding startups on AI product strategy, with deep experience across healthtech, marketing tech and enterprise SaaS. He also co-leads the Toronto chapter of The Product Folks.
Read Speaker Bio
Matthew Tobiasz is the co-founder and General Partner at Sightglass, a product and technology studio that integrates business strategy, product design, and engineering to create solutions for unmet needs. At Sightglass, Matthew partners with founders and executives facing critical product decisions—what to build, why it matters, and how to deliver it. He translates early market signals and competing priorities into clear product strategy and shippable roadmaps that drive business outcomes. Prior to launching Sightglass, Matthew led delivery teams at ThoughtWorks and served as Director of Experience Design and Strategy at UKG.




