In this episode of Strategy Shift, hosts Adam Levin and Tom Freedman sit down with Lance Keene — founder of Keene Systems and a master of custom software development — to talk about the tech challenges facing small businesses and how tailored web applications can streamline operations and unlock growth. From humble spreadsheet beginnings to $200 million transformations, Lance shares stories from the field and breaks down why customization matters. Plus, we take a detour to the mountains of New Hampshire to hear about Lance’s off-grid, 25-year quest to build his dream medieval castle by hand.

In Episode 3 of the Strategy Shift Podcast, Adam Levin and Tom Freedman talk with Matt Ruck, Founder & CEO of xop.ai, an automation and AI consultancy transforming IT services. Matt, formerly the CEO of designDATA, shares his expertise in building secure IT infrastructures and developing AI-powered solutions like self-help IT and HR chatbots that empower end-users to resolve issues independently. He discusses how AI and automation are reshaping IT services, enhancing knowledge management, and boosting business efficiency, while emphasizing the importance of implementing safe and trustworthy AI solutions.

In this episode, we dive deep into the unique challenges and strategies involved in hiring for small businesses. Our guests, Robyn Grable, Founder and CEO of Talents ASCEND, and Tobey Wyatt, Founder of Motherlode, share their insights on how small businesses can overcome the reactive hiring process and build a team that truly supports their long-term goals. From creating effective job descriptions to ensuring new hires align with your company’s vision, we explore the importance of strategic planning in recruitment. The conversation also touches on skills-based hiring, setting clear expectations, and finding candidates who thrive in lean, high-pressure environments. Whether you’re a small business owner or involved in recruitment, this episode offers practical advice to build a strong, purpose-driven team.