Matt Strippelhoff

Managing Fear of Automation: A Guide for Midmarket CEOs

Mid-market CEOs: Turning Job Fear Into Workforce Momentum

TL;DRMid-market CEOs are navigating a dual challenge: adopting transformative technologies like automation and AI while addressing employee fears of job loss. The most effective leaders don't dismiss these fears-they acknowledge them, reframe technology as an enabler, invest in reskilling, and lead with empathy and transparency. This approach not only reduces...
Build vs Buy

Build vs Buy: The Big Software Disruption

TL:DRMid-market companies face a unique challenge: enterprise ERP and CRM systems are too heavy, while lightweight SaaS tools are too shallow. This "fit gap" forces leaders to make tough build vs. buy decisions. Buying delivers speed and vendor support but can be rigid and costly to customize. Building enables differentiation...
Education and Upskilling: Preparing the Workforce for an AI Future

Education and Upskilling: Preparing the Workforce for an AI Future

TL:DRArtificial intelligence isn't coming - it's here, and it's reshaping the way we work. The winners in the AI economy won't be the companies with the flashiest tools, but those with the most adaptable people. Shift from Automation to Augmentation: AI isn't replacing humans - it's amplifying creativity, judgment, and...
Streamline and Scale Issue 3 - The AI Advantage: Faster Flow, Sharper Decisions, Stronger Teams

The AI Advantage: Faster Flow, Sharper Decisions, Stronger Teams

Vol. 1, Issue 3 A Message from Matt AI isn't replacing teams - it's empowering them to move faster, build smarter, and focus on what matters most. Over the past two issues of Streamline & Scale, we've been laying the groundwork for scaling intentionally. In Issue #1, we focused on...