The evening opened with a captivating performance by accomplished Grass and Hoop Dancer Terrance Littletent. Through song, dance and storytelling, Terrance shared a powerful expression of culture that bridges traditional and contemporary styles, he has carried that legacy across North America and overseas as a world-renowned performer and educator.

Following the performance, Michele Romanow—“Dragon” on CBC’s Dragons’ Den and Co-founder of Clearco took the stage for her keynote, Your Roots Are Not Your Limits: Why Where You Begin Doesn’t Define Where You End Up. Drawing from her journey from Saskatchewan to becoming one of Canada’s most prominent technology entrepreneurs and investors, Michele offered an honest and inspiring perspective on ambition, resilience and challenging the stories we tell ourselves about what is possible.

A serial entrepreneur who launched six companies before turning 35, Michele has built and invested in businesses with global reach. Through Clearco, she helped create the world’s largest e-commerce investor, which has invested more than $5 billion in 10,000 entrepreneurs across 13 countries. During her keynote, Michele reminded attendees that a local idea can have a global impact and that where you begin should never determine how far you can go.

Throughout the day, companies from our early-stage START and BUILD programs were on-site showcasing what they’re building, connecting with attendees and sharing their stories. It was a great opportunity to see the ideas and businesses coming out of our programs firsthand and have conversations with the founders behind them.

Nicole Parmar Co-founder and CEO of Gunkii, AI Business Analyst and GTM Specialist at Colibri Group, and Founder of JNJ Business Strategies – joined Michele Romanow for The Boat, the Caviar, and Everything in Between at the Women in Tech Breakfast.

Having built, sold and invested in companies – and advised founders from both sides of the table – Nicole brought an honest perspective to a candid conversation about ambition, setbacks, sacrifice and building a life and company on your own terms.

Together, Nicole and Michele reflected on their journeys through business and technology, including the realities of entrepreneurship that are rarely discussed on stage. They also spoke candidly about Regina and Michele’s experience returning to the city where her entrepreneurial journey began. Over a hot breakfast and coffee, attendees gained new perspectives while connecting with entrepreneurs, professionals, students and community builders from across Saskatchewan.

Alison Anderson, Founder of SuccessionMatching, moderated a candid conversation about how building a startup has changed in the age of AI. Having grown her Moose-Jaw launched company into a private equity-backed marketplace and now leading its U.S. expansion from New York City, Alison brought firsthand knowledge of the highs and lows of “Startupland.” She returned for Startup Summit because she believes Saskatchewan companies have a genuine market advantage, and need to give themselves permission to dream bigger.

She was joined by Andrew Wahba, President of Silk Logic, who helps organizations navigate AI-driven digital transformation, and Greg Sutton, CEO and Co-founder of TinyEYE Therapy Services, a Saskatchewan startup that has delivered more than one million online therapy sessions worldwide.

Together, the panel explored how AI is reshaping fundraising, hiring, product development and scaling. The speakers challenged founders to reconsider outdated approaches, offering practical perspectives on what entrepreneurs need to stop doing—and what they should start doing—to build and grow in today’s rapidly changing environment.

Tanner Goetz, Co-founder of HomeTeam Network (HTN), shared his experience building for national and global audiences while remaining connected to Saskatchewan. HTN is creating AI-powered infrastructure that brings professional-quality live broadcasting to underserved sports, including independent baseball, flag football and curling. His story demonstrated how Saskatchewan founders can build ambitious companies with reach far beyond the province.

Katrina German and Jordan McFarlen examined the funding options available to Prairie founders—and what actually makes sense when building an ambitious company in a smaller market.

Katrina, Founder of Ethical Digital, is a three-time tech co-founder, Forbes-signed author and one of Canada’s Top 25 Women in Tech. Jordan is the Managing Director of Conexus Venture Capital, where he oversees more than $60 million in assets and investments in high-growth Prairie technology companies, including 7shifts, Coconut and Vendasta.

Drawing on their experience building, advising and investing in companies, Katrina and Jordan compared bootstrapping, angel investment, venture capital and revenue financing. The session offered founders a practical perspective on choosing the right capital for their goals while building from the Prairies for a global market.

Matt Fahlman, Co-founder and CEO of Offstreet, shared practical customer acquisition lessons from his experience building and scaling a Saskatchewan startup. Under his leadership, the parking permit management software company has grown to a team of 40 and now serves more than 100 campuses. His founder story offered an honest look at what it takes to find customers, build momentum and turn an early-stage idea into a growing company.

Matt even had is own hype squad cheering him on!

Romeo Iula, CTO and Co-founder of Coconut Software, shared the real story of selling into large organizations when nobody knows who you are. A web developer and lifelong student of technology, Romeo is guided by data, creative problem-solving and a belief that even complex challenges can be solved simply. His founder story offered a practical look at earning trust, navigating enterprise sales and building credibility from the ground up.

Charlyne Fothergill and Dean Clark came together for a fireside chat on building scalable companies through focus, disciplined execution and lean teams.

Charlyne, Founder of Sova Operations, brought 15 years of experience supporting Canada’s technology ecosystem through business strategy, talent and people operations. Dean, Founder and CEO of Regina-based Greenwave Innovations, shared lessons from building technology companies and leading Greenwave’s data-driven approach to energy and asset management.

Together, they explored how founders can scale sustainably by setting clear priorities, executing consistently and building effective teams without unnecessary complexity.

Jon Giambattista, co-founder of Limbus AI, moderated a fireside chat with iOrders co-founders Rakesh Pillai and Dhanesh Udayan about building a rapidly growing company, entering new markets and continuing to think bigger while remaining rooted in Saskatchewan.

A 2023 Cultivator graduate, Limbus AI scaled to support hundreds of cancer centres worldwide before being acquired by Radformation in 2024. Drawing from that experience, Jon guided a conversation with Rakesh and Dhanesh about how they grew iOrders from two founders in Regina into a restaurant technology platform serving thousands of restaurants across Canada.

The conversation explored the journey behind iOrders and its mission to give independent restaurants commission-free online ordering, AI-powered websites, loyalty tools and automated marketing—helping operators retain ownership of their customers and revenue.

Jason Tennenhouse closed Startup Summit with The Can’t Not, a powerful keynote centred on the people who help founders endure the most difficult stages of building something new.

An eight-time founder and three-time author, Jason has spent more than 25 years building and coaching ventures across the United States and Europe. His experience includes senior strategy roles with Google, Cummins, Purdue University and the Obama White House, along with supporting more than 500 ventures that have collectively raised over $300 million and generated more than $1 billion.

Jason reminded attendees that no founder survives the trough alone. His closing message emphasized commitment, resilience and the importance of finding a community that can help illuminate the way forward.

Modern GTM: How Startups Win Attention in 2026

Nicole Parmar delivered a tactical breakdown of how startups are approaching go-to-market strategy today. From founder-led growth and AI-assisted outreach to practical customer acquisition tactics, the workshop gave founders actionable ideas for earning attention and reaching the right customers.

Ready to Raise? How Investors Really Make Decisions

Chetan Srivastava, Principal at TELUS Global Ventures, took founders beyond simply polishing another pitch deck. Drawing from his investment experience, Chetan explored how to approach fundraising strategically, build meaningful investor relationships and position a company for a successful raise.

Aliens vs. Robots: Why Your Weird, Human, Unscalable Advantages Still Win – Workshop powered by Growclass

Talitha McCloskey of Growclass challenged founders to see being small as an advantage. Through an interactive workshop, she explored how staying close to customers, building genuine relationships and doing intentionally unscalable things can turn early customers into collaborators and advocates.

Distilling 20 Years of Experience into an AGENTS.md File

JavaScript and front-end consultant Adam Barrett distilled two decades of coding experience into practical lessons for the age of agentic development. The session explored how developers can keep code organized and simple while applying proven fundamentals to new AI-assisted workflows.

Don’t Replace Yourself: Polishing Your Authentic Career Story with AI

Technology leader and AI practitioner Kate Nimegeers demonstrated how job seekers can use AI to build stronger, more accurate resumes and communicate their value more clearly. Drawing from her experience in AI adoption and talent recruitment, Kate showed attendees how to enhance their personal brands without sacrificing authenticity.

The Sniff Test for Dirty Data

Educator and Founder of Janice Cotcher Data & Design, Janice Cotcher explored how to clean, transform and extract value from raw data ethically. Attendees learned the importance of maintaining a clear “chain of custody” while turning complex information into reliable, usable insights.

The Dev Track was powered by Hack Regina, helping bring together developers and technology professionals for practical conversations about coding, AI, careers and data. A huge thank you to Hack Regina for supporting a space where Saskatchewan’s developer community could learn, connect and grow.