This mini episode unpacks how misalignment between leadership, IT, and operations turns AI initiatives into duplicated work and surprise deployments. We discuss what happens when IT builds “for the business” without shared requirements, when the business buys tools without IT, and how a vague mandate to “go use AI” creates competing solutions. The focus is on rebuilding communication, trust, and tactical alignment so AI workstreams stay coordinated and outcome-driven.

Watch the full episode here: https://youtube.com/live/KI-lnkDspKg 

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This mini episode breaks down one of the hardest leadership challenges in SaaS delivery: knowing the difference between work that is difficult and work that is broken. We explore how poor governance turns normal project friction into unnecessary escalations, why not every disagreement should move up the chain, and how disciplined decision structures prevent credibility loss, rework, and wasted spend. The focus is on building escalation paths that surface real issues without rewarding preference-driven overrides.

Watch the full episode here: https://youtube.com/live/aSP6jCk3twc?feature=share 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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This mini episode explores when rework is a normal part of SaaS delivery and when it signals a deeper discipline problem. We discuss how to distinguish fixable issues from systemic risk, why testing always includes rework, and how strong leadership and transparency prevent small problems from becoming project failures.

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/  

This mini episode examines the cost of discovering missing requirements late in SaaS projects. We discuss how gaps in requirements and weak governance drive scope, timeline, and delivery risk, and why discipline must be structural rather than punitive. The key takeaway is that addressing missed requirements during implementation is far less costly than absorbing the impact after go-live.

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/  

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/  

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/  

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/  

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 

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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/  

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/