The prairies are home to exceptionally resilient founders, and sometimes Saskatchewan doesn’t receive the recognition it deserves. That’s why we position Startup Summit as a unique opportunity to spotlight our talented founders and introduce them to top-tier investors. We aim to foster more connections, increase capital raised, and ultimately create more success stories originating from Saskatchewan.
Click to expand the following sections as we look back at Startup Summit 2023…
To kick things off, Jordan Boesch, the CEO of 7shifts, led a locked-down session for founders only. With a background that includes founding and leading 7shifts, the premier restaurant team management platform, Jordan’s journey began as a simple solution to aid his father’s Quiznos franchises in work schedule management. Today, 7shifts serves over 40,000 restaurants, earning the trust of esteemed brands like Danny Meyer’s Union Square Hospitality, Bartaco, Halal Guys, and Boka Restaurant Group. With over 1 million restaurant professionals relying on the platform, Jordan Boesch’s workshop provided exclusive insights and lessons from his remarkable entrepreneurial journey in the tech industry, making it an invaluable experience for founders to ask burning questions under Chatham House rules.
An action-packed day one of the conference saw an abundance of support, resources and content geared specifically towards founders and startup team members. The afternoon unfolded with a series of curated one-on-one meetings between founders and investors. These strategic meetings allowed each founder the access and unique opportunity to engage with multiple investors from across the country, presenting their startups and passionately pitching their visions.
The resounding success of these meetings was evident through the overwhelmingly positive feedback received, from both founders and investors, underscoring the Summit’s role as a catalyst for meaningful, curated connections. Investors gained valuable exposure into new and exciting startups, while founders acquired crucial insights into potential investment opportunities.
This year we decided to bring back the heat with another DevJam – hosted with Amazon Web Services (AWS).
Coders and developers from far and wide came together to chat all things tech right here in Regina at Startup Summit.
Kicking off the workshop, Regina’s very own Patrick Ullrich hit the stage to take us on a journey through the web’s transformative developer and user experience. He journeyed us from the early days of Multi-Page Applications using PHP, to the era of Single Page Applications, culminating with next-gen tech such as React Server Components.
With a room full of technical founders and developers from the community, Patrick brought his expertise as the Principal Software Developer at Offstreet, laying it all out on the stage for them. With a lot of jokes, hard truths, and insightful demonstrations – you just had to be there.
Next to hit the DevJam stage was Gustavo Fernandez, Senior Startup Solutions Architect at AWS. Gustavo brought value to the forefront, focusing on optimizing AWS as a startup. Attendees were enlightened with all the tips and tricks someone could need when it comes to working with AWS and account managers, and how to grow effectively and efficiently with AWS.
Talk the Talk: Mastering the Art of PR
Lauren shared her extensive expertise in various communication fields, including PR, thought leadership, social media, digital marketing, influencer relations, and branding. With a portfolio of prominent tech companies, Lauren’s commitment to industry advancement was evident in her role as Vice Chair of PR and Marketing for the #Tech4SickKids advisory council for SickKids. In the workshop, she offered valuable insights into media and storytelling’s importance in PR, providing attendees with enlightening strategies and knowledge.
Designing Great Places to Work: A Hands-On Roadmap for Founders
Nora Jenkins Townson, founder of Bright + Early, is well-known for transforming startups like Wealthsimple and Freshbooks. With a passion for creating exceptional workplaces, she founded Bright + Early, a consultancy that’s made its mark on companies like Mozilla, Mejuri, Endy, and Kotn, fostering inclusive and people-centric environments. Nora’s approach prioritizes people, data, and design thinking in HR strategies.
Selling Success: 5 Ways to Attract Investors
In a highly informative workshop, Craig Elias took the stage in his bright orange shirt (a classic staple in Craig’s wardrobe) to share his wealth of knowledge and experience in the world of startups and investment attraction.
Craig engaged the crowd, constantly asking questions and looking for answers to some of his hard-hitting questions.
Craig, who holds the prestigious LinkedIn user number 3,956 out of over 950 million users, boasts an impressive 10,000+ unsolicited endorsements, with more than 1,000 specifically acknowledging his expertise in lead generation. His expertise has earned him recognition as Canada’s #1 B2B Sales Expert by LinkedIn in both 2018 and 2019, a title he also holds on a global scale at #15.
McKercher Patio Party
McKercher LLP partnered with Cultivator to host an unforgettable patio party at Blanco Cantina that brought together a dynamic mix of founders, investors, and community members. With rain clouding the chances to soak up the rays on the patio, the venue was overflowing with attendees spilled out from both floors of the venue looking for the opportunity to connect and build meaningful relationships amidst the lively atmosphere.
With a day full of incredible content and speakers the patio party served as an ideal pit stop to relax, recharge and continue building a network.
The patio party gave guests the chance to explore the new, Mexican-inspired restaurant Blanco Cantina as they kept the tacos and drinks flowing. As the event came to a close guests made their way back to the Cultivator HQ to meet and mingle with founders in the Startup Showcase.
SK Startup Showcase - Presented by Innovation Saskatchewan
Cultivating Community Night successfully united the tech community at Cultivator’s HQ! The evening commenced with the Startup Showcase, where over 20 tech startups transformed the space with vibrant booths, banners, and balloons to promote their ventures and engage with curious attendees. It was akin to a startup-themed tradeshow, and the room buzzed with dynamic energy as founders and their teams proudly presented their companies to the community.
Cultivating Community is a night of celebration and community as guests visit the company booths at the Startup Showcase and listen to the founders’ stories.
The event began by welcoming the Yellow Creek Singers (lead singer Terrance Whitehead) to the stage, followed by three talented dancers: Patience Benjoe, who performed the women’s Jingle Dress dance known for its healing origins; Nadine Obey, dancing the Women’s Fancy Shawl, an athletic dance inspired by butterfly movements; and Vince Obey, performing the Men’s Fancy Bustle Dance, a fast-paced, competitive dance originating from Oklahoma with elements of style and footwork.
Indigenous representation and involvement at events like Startup Summit are not just important; they are essential to recognize and respect the rich cultural diversity that Indigenous communities bring to the table. Indigenous peoples have a deep connection to the land, traditional knowledge, and unique perspectives that can inspire innovation and creative problem-solving within the startup ecosystem. We are committed to working together with Indigenous peoples as we take important steps forward on the pathway of collaboration, reconciliation, and change.
Travis Keisig, MLA for Last Mountain Touchwood, representing the Government of Saskatchewan and Innovation Saskatchewan presented a warm welcome to the crowd. His presence underscored the government’s commitment to supporting innovation and entrepreneurship in the province.
Additionally, recognition was given to Conexus Credit Union for its pivotal role in nurturing Saskatchewan’s entrepreneurial ecosystem through the launch of Cultivator five years ago. Their dedication to the province and Cultivator’s mission was evident through the words of Chief Growth Officer, and Cultivator Advisory Council Member, Maggie Sinclair, who set the tone for an evening of collaboration and growth.
Catherine Metrycki‘s path exemplifies the transformative potential of entrepreneurship and community engagement making her a standout speaker at the event. She first graced the Startup Summit stage in 2019, where she pitched her innovative venture, Callia. Since then, her startup has not only received investment from Conexus Venture Capital but has also become a notable portfolio company.
Catherine’s story revolves around Callia, an enterprise she founded in 2017, aiming to revolutionize the flower and gift delivery experience across Canada. Under her leadership, Callia has flourished into a venture capital-backed business serving over 55 cities. Their recipe for success includes a focus on high-touch online ordering, limited yet high-quality seasonal offerings, flawless delivery, and their distinctive blue box.
Callia’s achievements have been widely recognized, including appearances on CBC Dragons’ Den and rankings as one of Canada’s fastest-growing companies. Catherine’s commitment to fostering a positive workplace culture is evident in Callia’s recognition as one of the Best Workplaces in Canada by the Great Place to Work certification program.
Beyond her entrepreneurial endeavors, Catherine actively contributes to the business community as a mentor and board member, reflecting her passion for coaching and development. Her multifaceted journey, which now includes the role of a proud mother, embodies the spirit of founder journeys and the sense of community they bring to life. Catherine Metrycki’s success story is an inspiration to all aspiring entrepreneurs and a testament to the power of innovation and dedication.
Tanner Goetz’s founder journey is a testament to the growth and innovation fostered by platforms like Cultivator. As an integral part of Cultivator from its inception and a winner of START Cohort 5’s demo day on the Startup Summit stage in 2021, Tanner’s story continues to inspire the entrepreneurial community in Regina.
Tanner initiated HomeTeam Live by live-streaming local minor sports events, often broadcasting from parking lots, showcasing the grassroots origins of his venture. Yet, his vision quickly transcended local boundaries, propelling him to international recognition.
Tanner’s journey epitomizes the innovative and adaptive spirit of the tech and streaming industry. His narrative serves as an inspirational illustration of how startups can evolve and prosper within a dynamic landscape. Tanner’s unwavering dedication to advancing live-streaming technology undoubtedly conveyed valuable insights to aspiring entrepreneurs in the audience, emphasizing the importance of persistence in the face of challenges.
The evening concluded with Dan Simair, a renowned founder hailing from the prairies. His journey began in 1999 with a Computer Science program at UofS, followed by a decade in enterprise software consulting. Notably, he played a pivotal role in founding SkipTheDishes, culminating in a $200 million exit in four years.
Dan’s entrepreneurial spirit extended to founding Pivot, where he reimagined how consumers furnish their homes. His dedication to social change through entrepreneurship left a lasting impact on the event, underscoring the potential for entrepreneurs to drive meaningful change and inspire others.
Women in Tech Breakfast
The second day of Startup Summit kicked off with a SOLD OUT Women in Tech Breakfast hosted at Hotel Saskatchewan. This gathering aimed to promote and celebrate women’s leadership in the tech industry. It welcomed a diverse audience, inviting all to come together to unlock the potential of women in technology.
Attendees had the opportunity to enjoy a hot breakfast, coffee, and engaging conversations in a beautiful setting. The event emphasized the importance of collaboration and networking, bringing together advocates and change-makers who are dedicated to advancing education and inclusion within the tech sector.
Women in Tech Breakfast: Laura Gabor + Juanita Lee-Garcia
Notably, the event received support from the National Angel Capital Organization (NACO Canada), underscoring the significance of their mission.
Laura Gabor, a seasoned operations specialist and passionate advocate for community building and women’s empowerment, joined forces with Juanita Lee-Garcia, Executive Director at the Upside Foundation of Canada, in a powerful collaboration. Together, they orchestrated an emotional and empowering conversation about women in tech. Laura’s extensive experience in operations and her role as Summit Content lead, combined with Juanita’s background in tech, philanthropy, and large-scale systems change, created a dynamic duo dedicated to spotlighting the challenges and successes of women in the technology industry.
Rapid Fire Stories
Up next, we had the opportunity to hear from 5 rapid-fire keynotes inspiring women in the tech ecosystem sharing their experiences, stories of resilience, collaboration and advice to the audience…
In essence, this gathering served as a vital initiative to empower and elevate women in technology, fostering a sense of unity and collaboration within the industry – further sparking the conversation with allies in the room on how we can create a more inclusive path forward.
Elder Dennis Omeasoo
After the breakfast, guests made their way back to Cultivator HQ to take in a jam packed schedule of content!
Our conference opened with a traditional land blessing and opening prayer from Elder Dennis Omeasoo.
Canada’s Investment Landscape: Opportunities, Trends, and Beyond
Matt Roberts, a seasoned expert in Canada’s investment landscape, delivered a compelling keynote during the first session of Day 2.
As a co-founder and General Partner at CMD Capital, with a particular focus on Seed opportunities in AI, Matt brought a wealth of knowledge and experience to the stage. His impressive track record, including his roles at ScaleUP Ventures and leadership in various startups, showcased his deep involvement in the tech and investment ecosystem. Matt’s extensive portfolio of investments in companies like Unsplash, Sonder, and Hubdoc made his perspective particularly impactful.
Building Brand Confidence: How to Bring Clarity to Your Startup Story
As the head of a brand strategy and design studio, Jared’s insatiable curiosity and dedication to helping clients tell their stories in a clear and compelling manner shone through in his presentation. Jared emphasized the pivotal role that strong brands play in shaping the future and highlighted the importance of collaboration for positive change.
Dollars and $ense: You’ve Raised Some Capital, Now What?
Catherine’s extensive experience in the entrepreneurial landscape, especially in the context of raising capital, offered valuable perspectives to the audience. Claudio’s role as a moderator added a layer of expertise to the conversation, guiding critical questions throughout.
Together, they delved into the intricacies of what comes after securing investment, providing a wealth of practical insights and knowledge that were invaluable to those looking to navigate the complexities of post-capital-raising strategies. This fireside chat showcased the importance of such discussions in empowering entrepreneurs and fostering a deeper understanding of the financial aspects of running a successful startup and what it means for their team.
Day two featured a dynamic event called Raise Room, where founders seized the opportunity to pitch their ventures to a room filled with eager investors. In just three minutes, each founder presented the core components of their business and advocated why they were the perfect match for potential investors. With a total of five companies stepping up to the plate (chosen through registration criteria), the room was lively with innovation and potential partnerships. The Raise Room not only provided a platform for startups to shine but also facilitated meaningful connections between founders and investors in a confidential and casual environment.
Chaos to Control: Unlocking the Secrets to Productivity and Balance
Tarra Stubbins, Founder and CEO of Take It Easy Group, shared a wealth of experience as a certified lifestyle manager, accountability and time management coach, and celebrity concierge. Tarra’s insights into productivity and balance were both enlightening and practical as guests had many “ah-ha” moments. She shared her passion for helping time-strapped executives and entrepreneurs achieve their personal and professional goals. Drawing from her years of managing demanding schedules for rock star celebrities (like Mick Jagger) and high-profile CEOs, Tarra offered a treasure trove of hands-on experience and real-time management strategies.
Exit on the Prairies: Second Time Founders Back For More
The panel discussion featuring Saskatchewan’s accomplished entrepreneurs un doubtably a highlight of the event. These exceptional founders shared their experiences and insights on successfully exiting their companies and entering the exciting ventures they are currently involved in. This particular panel underscored the importance of learning from those who have walked the path before and showcased the thriving entrepreneurial spirit within Saskatchewan.
Getting Back Up: Building a Competitor Mindset
Jenessa Olson, drew a captivating parallel between launching a startup and becoming a high-performance athlete. With her experience as a two-time founder and former professional athlete, Jenessa shared invaluable lessons learned through failures, discipline, and the guidance of the right mentors. She emphasized the qualities of tenacity, resilience, and an unwavering determination to never give up, which are essential both in the world of sports and in entrepreneurship. Her personal journey served as a motivating example of how the lessons learned in one field can be applied to excel in another, leaving the audience with a renewed sense of determination and a toolkit for success to drawn on their own personal backstories.
Show Me the Money: How to Get the Answer You Want From Investors
Rob Russell – Principal, Conexus Venture Capital & Emmertech
Cultivator’s commitment to facilitating investor connections and resources for founders was highlighted in this session. The panelists shared invaluable insights and advice on how entrepreneurs can create compelling pitches and strategies that make it easy for investors to say “yes” to their companies. Their expertise and diverse backgrounds in investment provided attendees with a comprehensive understanding of the investor landscape, empowering them to navigate the challenging terrain of raising capital more effectively.
Startup Social - Hosted by Conexus Venture Capital
To conclude Startup Summit 2023, Conexus Venture Capital hosted a Startup Social. The event celebrated the invaluable connection of Conexus Venture Capital and Emmertech, which has played a pivotal role in providing Saskatchewan and Canadian tech founders with access to capital. Attendees were welcome to close the conference casually over drinks and ensure that they wrapped up any outstanding conversations with potential business connections.
Over the span of two days, we had the pleasure of hosting some of North America’s most accomplished tech leaders in Saskatchewan. It was an exciting opportunity for us to serve as the central hub for investors and funds from all corners of the country. Our core mission was to foster valuable connections between founders and investors, which is especially vital in these challenging fundraising times. We are filled with anticipation as we wait for the positive outcomes that emerge from this event as attendees apply their newfound knowledge to their startups, scaling to new heights!