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]
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From Survival to Strategy (Matthew Kaisaris and Jamie Schneiderman)
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