ByteSized

Governance and Change Intelligence in SaaS Implementations

This mini episode explores how flexibility without governance leads to unnecessary customization in SaaS implementations. We discuss how to evaluate “my situation is different” requests, set clear scope and prioritization, and use change intelligence to focus teams on business outcomes instead of preferences.
 
Watch the full episode here: https://youtube.com/live/aSP6jCk3twc?feature=share 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/  Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

How to Write Effective SaaS Requirements

This mini episode explains how to write effective requirements for a SaaS solution. We cover how requirement depth should align to purpose, from high level capabilities used in vendor selection to detailed functional requirements needed for configuration and build. The discussion highlights why vague language leads to vendor driven outcomes and how clear, testable requirements create control, alignment, and better implementation results.
 
Watch the full episode here: https://youtube.com/live/aSP6jCk3twc?feature=share 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/  Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Managing Scope Certainty in SaaS Statements of Work

This mini episode explores why SaaS Statements of Work can never fully eliminate ambiguity and how organizations should plan for that reality. We discuss unknown requirements, the inevitability of change orders, and how stronger upfront discovery helps reduce risk, control cost, and evaluate scope changes without losing momentum.
 
Watch the full episode here: https://youtube.com/live/RNuGSva75qo?feature=share 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/  Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Contracting for Probabilistic AI in SaaS Platforms

This mini episode explores why traditional SaaS contracts break down when applied to probabilistic AI systems. We discuss the limits of using generative AI for contract review, how liability and accountability are shifting, and why AI clauses increasingly resemble professional services disclaimers. The conversation centers on risk ownership, decision authority, and why organizations remain responsible for outcomes, even when AI drives the recommendation or action.
 
Watch the full episode here: https://youtube.com/live/RNuGSva75qo?feature=share 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/  Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Establishing Contractual Authority in SaaS Agreements

This mini episode explores why SaaS contract review requires more than a surface read. We discuss the need for experienced authority in interpreting licensing, legal terms, and commercial structures, why legal and financial negotiations must happen together, and how gaps in expertise can lead to excess cost or long-term risk baked into the agreement.
 
Watch the full episode here: https://youtube.com/live/RNuGSva75qo?feature=share 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/  Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Speed vs. Clarity in SaaS Contracting

This mini episode focuses on balancing speed and clarity during high-pressure software contracting. We discuss why rushing increases risk, how vendor pressure shapes timelines, and practical ways leaders can move quickly without making costly mistakes.
 
Watch the full episode here: https://youtube.com/live/RNuGSva75qo?feature=share 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/  Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 
 
 

Can You Really Handle System Ownership in an AI Security Era

This mini episode explores the tradeoffs between system ownership and shared responsibility through SaaS, using cybersecurity as the lens. We discuss how AI driven threats change the risk equation, when owning your technology becomes a liability, and how vendor scale can shift security responsibility. The conversation closes with a practical decision framework focused on pain points, root cause analysis, and solution options that extend beyond software replacement to include process and policy change. The goal is to help leaders make grounded, healthy technology decisions without jumping to predetermined answers.
 
Watch the full episode: https://youtube.com/live/RnKYGv9bdVQ 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/  Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

The True Cost of Modernization Ownership Risk and Security Tradeoffs

This mini episode breaks down what modernization really costs beyond the price tag. We discuss uncovering operational expenses tied to legacy systems, separating business value from sales-driven promises, and why discovery takes time. The conversation also explores ownership versus vendor dependency, business risk, and how AI-driven cyber threats are reshaping security decisions. The focus is on choosing the right path based on capability, control, and long-term risk.
 
Watch the full episode: https://youtube.com/live/RnKYGv9bdVQ 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

The Real Legacy Risk Losing the People Who Know the System

This mini episode looks at why legacy system challenges are often less about technology and more about people. We discuss how over customization, retiring experts, and undocumented knowledge leave organizations unsure of how their systems actually work. The conversation explores workforce lifecycle risk, talent availability, and the tipping point where maintaining legacy expertise becomes unsustainable. The focus is on recognizing when it is time to transition with intention rather than waiting until critical knowledge walks out the door.
 
Watch the full episode: https://youtube.com/live/RnKYGv9bdVQ 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

When Systems “Can’t” Deliver: Product Limits vs Business Priorities

This mini episode breaks down a common claim in technology discussions: “our system can’t do X.” We explore how often this reflects a true product limitation versus a lack of understanding, experience, or prioritization. The conversation looks at how enhancement backlogs form, how unmet requests compound over time, and when rebuilding internally costs more than change. We also examine the tradeoffs of SaaS driven enhancements, security and compliance pressures, and why discovery and honest prioritization matter more than assumptions or vendor-driven narratives.
 
Watch the full episode: https://youtube.com/live/RnKYGv9bdVQ 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial