From Survival to Strategy (Matthew Kaisaris and Jamie Schneiderman) episode artwork

EPISODE · Apr 22, 2026 · 21 MIN

From Survival to Strategy (Matthew Kaisaris and Jamie Schneiderman)

from Unstuck Pod · host Jamie Schneiderman

In this episode, Jamie welcomes Matthew, the CEO and founder of Boreal Systems, to discuss the journey of starting a consultancy in the rapidly evolving landscape of work management platforms. Matthew shares the Boreal Systems story, detailing his transition from working in the Monday.com ecosystem to launching his own business. The conversation explores the benefits of optimizing workflows and the impact of AI on project management. Matthew also delves into the challenges of initial growth and the shifting dynamics of client relationships in the digital age. Whether you’re a security professional, team leader, or just curious about the future of work management tools, this episode offers practical insights on navigating the complexities of the industry.🔗 Guest & Resources  Connect with Matthew: https://www.linkedin.com/in/matthewkaisaris/  Check out Boreal Systems: https://www.borealsystems.ca🤝 Connect with Me: https://www.linkedin.com/in/jamieschneiderman/  Unstuck Your Business: www.unstuckyourbusiness.com📌 Chapters  00:00 – Welcome and Introduction to Matthew  00:36 – Understanding Boreal Systems  01:43 – Matthew's Journey and Insights  02:30 – Major Shifts in the Industry  04:11 – Key Technologies and Innovations  05:37 – Market Demands and Challenges  06:54 – Opportunities and Cautions in the Field  09:42 – Real-world Applications  11:13 – The Future of Content and Learning  12:17 – Insights on Collaboration and Teamwork  14:13 – Strategies and Best Practices  15:20 – Balancing Creativity and Growth  16:56 – Lessons Learned  18:24 – Engaging with Boreal Systems  19:56 – Final Thoughts and Key Takeaways  🔑 Keywords  startup finance, investor readiness, due diligence, financial modelling, startup reporting, fundraising preparation, SaaS metrics, tech founders, cash flow management, management accounts, financial operations, startup compliance, data room management, VC expectations, scaling finance systems  👉 Want to be on the podcast? Send an email to [email protected]

Episode metadata supplied by the publisher feed · Published Apr 22, 2026

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From Survival to Strategy (Matthew Kaisaris and Jamie Schneiderman)

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