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PODCAST

ByteSized

Hi, I’m Kyler Cheatham, host of the ByteSized podcast, where we dive into the dynamic world of digital transformation and its impact on businesses today. Each episode features insights from industry experts and thought leaders who share their experiences, challenges, and successes in navigating enterprise tech. From Industry 4.0 to SAP S/4HANA, ERP, artificial intelligence, and beyond, our experts unpack it all! Subscribe now and transform the way you think about technology in your business!

technology

All Episodes

5:19

Disconnected Change Management Undermines ERP and AI...

ByteSized ·

2026/01/15

This mini episode explains how separating change management from project execution creates misalignment in ERP and AI initiatives. We explore why vague AI strategies, language gaps between IT and operations, and uncoordinated execution lead to surprise deployments, duplicated work, and eroded trust. The focus is on aligning delivery and change to prevent technology from amplifying organizational disconnects.Watch the full episode here: https://youtube.com/live/KI-lnkDspKg Connect with me on

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6:05

Domain Expertise and Fit-Gap Analysis in Complex SaaS...

ByteSized ·

2026/01/14

This mini episode explores why domain expertise is critical when selecting partners for complex technology initiatives. We discuss how vendors can unintentionally add complexity, why industry-specific processes are often invisible to outsiders, and how weak fit gap analysis leads to late-stage surprises. The conversation highlights the importance of translating business requirements into technical solutions through deep process understanding, especially in asset-intensive and highly specialized

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4:11

Closing the IT Operations Gap for AI and Data

ByteSized ·

2026/01/13

This mini episode explains why strategic alignment is not enough when complexity rises. We discuss tactical alignment between IT and operations, how interdependencies create disconnects, and why data platforms often expose the problem through inconsistent metrics. The focus is on planning methods that make work visible, surface process disparities, and help teams align at a granular level, so AI and technology initiatives can deliver real outcomes.Watch the full episode here:

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3:13

AI Strategy Drift When IT and Operations Build in...

ByteSized ·

2026/01/12

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:

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12:37

Making Escalation Decisions in SaaS Projects

ByteSized ·

2026/01/09

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

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2:50

When to Pause a SaaS Project and When to Push Forward

ByteSized ·

2026/01/08

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.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

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2:40

Cost and Risk of Late Requirement Discovery in SaaS...

ByteSized ·

2026/01/07

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

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5:03

Governance and Change Intelligence in SaaS...

ByteSized ·

2026/01/06

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

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5:36

How to Write Effective SaaS Requirements

ByteSized ·

2026/01/05

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:

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3:25

Managing Scope Certainty in SaaS Statements of Work

ByteSized ·

2026/01/02

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

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5:26

Contracting for Probabilistic AI in SaaS Platforms

ByteSized ·

2025/12/31

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:

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4:05

Establishing Contractual Authority in SaaS Agreements

ByteSized ·

2025/12/30

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

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2:56

Speed vs. Clarity in SaaS Contracting

ByteSized ·

2025/12/29

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

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5:56

Can You Really Handle System Ownership in an AI...

ByteSized ·

2025/12/19

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

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4:48

The True Cost of Modernization Ownership Risk and...

ByteSized ·

2025/12/18

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:

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4:14

The Real Legacy Risk Losing the People Who Know the...

ByteSized ·

2025/12/18

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

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6:07

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

ByteSized ·

2025/12/16

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

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6:43

When Legacy Systems Outperform Modern Software

ByteSized ·

2025/12/15

This mini episode explores why older systems sometimes deliver more value than newer software and why replacing them should never be an emotional decision. We break down how to assess real pain points, distinguish usability issues from functional limitations, and identify when a system truly can no longer support growth. The conversation also examines the long-term cost of ownership, rising SaaS subscription risk, over-customization, workforce considerations, and licensing constraints. The takeaway

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4:03

Human–AI Workflows and the Reality of Enterprise...

ByteSized ·

2025/12/12

This mini episode examines what low automation rates and increasing autonomous task capability really mean for the next 24 months of human AI workflows. We discuss why full autonomy remains rare, how AI should build organizational capacity rather than simply replace labor, and why prompt training alone is not an AI strategy. The conversation focuses on practical integration, data readiness, and the gap between AI experimentation and real workflow automation in the enterprise.Watch full episode

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3:49

Cutting Through AI Noise with Practical Integration...

ByteSized ·

2025/12/11

This mini episode explains how to navigate AI adoption without getting pulled into market hype. We discuss why simple approaches work, why end user engagement matters, and how to avoid vendor lock-in when building AI capabilities. We outline the importance of owning your strategy and show why effective integration depends on change intelligence working directly with project execution. The episode offers a clear, disciplined approach to adopting technology in a noisy marketplace. Watch full episode

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131 results

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