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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

6:28

What Canada’s IT Failures Reveal About Vendor...

ByteSized ·

2026/04/09

Massive public sector IT failures are not just about technology. This episode unpacks how vendor dependency, poor contracts, and lack of accountability have led to billions in taxpayer losses and repeated breakdowns. It also highlights the real-world consequences and what organizations can learn to avoid the same costly patterns.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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2:27

How AI Agents Are Disrupting SaaS Revenue Models

ByteSized ·

2026/04/08

AI agents are changing how work gets done, from automating customer support to reducing the need for traditional SaaS seats. This episode breaks down how these shifts are impacting platforms like Salesforce and why vendors are racing to layer AI into their offerings. It also explores the risk of adopting AI reactively instead of aligning it to real business needs.Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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3:56

Are You Wasting Millions on Microsoft Copilot?

ByteSized ·

2026/04/08

Many organizations are rushing to buy Copilot licenses without a clear plan, assuming security and value come built in. This episode breaks down the real numbers, low adoption rates, and hidden risks behind AI “check-the-box” decisions. It also highlights why governance, strategy, and actual usage matter far more than the logo on the tool. 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

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5:21

Is the SaaS Apocalypse Real or Just Market Hype?

ByteSized ·

2026/04/06

The so-called SaaS Apocalypse is forcing organizations to rethink how they invest in software and prove real ROI. This episode explores how AI agents, tool sprawl, and shifting market expectations are changing the value of traditional SaaS platforms. It also breaks down what operators and leaders need to understand before jumping into the next wave of technology. Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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2:00

Who’s Really Responsible for Shadow IT in Your...

ByteSized ·

2026/04/03

Shadow systems are not created by bad employees. They are a symptom of leadership gaps, unclear communication, and tools that fail to meet real business needs. This episode explores why accountability starts at the top and how modern IT teams must evolve into true business partners to prevent risk and regain control.Watch the full episode here: https://www.youtube.com/live/Gv4vefu_yfo Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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7:35

Why There’s No Accountability in Failed ERP...

ByteSized ·

2026/04/02

Failed implementations are rarely accidents. This episode breaks down how rushed contracts, misaligned incentives, and lack of legal diligence leave organizations exposed while vendors avoid accountability. It also explores real-world cases and why slowing down upfront is the only way to protect your business long term.Watch the full episode here: https://www.youtube.com/live/Gv4vefu_yfo Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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2:11

Organizations Keep Making the Same Technology Mistakes

ByteSized ·

2026/04/01

Technology failures are rarely just about systems. This episode explores how leadership decisions, lack of communication, and poor alignment create repeated breakdowns across organizations. It also dives into the real risks behind ERP investments, shadow systems, and why discipline and clarity matter more than chasing the next big solution.Watch the full episode here: https://www.youtube.com/live/Gv4vefu_yfo Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on

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4:11

How Do You Justify the Cost of an ERP Investment?

ByteSized ·

2026/03/31

Large technology investments rarely deliver immediate returns, which makes them difficult to justify. This episode explores how to frame long-term value, communicate ROI, and align leadership around the bigger picture. It also breaks down the real risks of ERP implementations, from cost and disruption to ongoing SaaS expenses.Watch the full episode here: https://www.youtube.com/live/Gv4vefu_yfo Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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4:27

How Much Should Executives Really Know About Technology?

ByteSized ·

2026/03/30

Technical expertise isn’t what makes executives effective in technology decisions. This episode explores why listening to internal teams and staying aligned with business needs matters far more than trying to be the expert. Strong leadership comes from balancing strategic priorities with trust in the people closest to the work. Watch the full episode here: https://www.youtube.com/live/Gv4vefu_yfo Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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4:07

Why Your Reporting Is Broken Even If Your System Isn’t

ByteSized ·

2026/03/27

Many organizations rely on Excel workarounds and disconnected reporting without realizing the root issue isn’t the system. This episode explores ownership of data, reporting responsibility, and the risks of over-relying on vendors or integrators. The focus is on creating a single source of truth and building reporting processes that actually support the business.Watch the full episode here: https://youtu.be/RZnuL2aEU1Y Connect with me on LinkedIn

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3:17

Should You Build or Buy AI Agents for Your Business?

ByteSized ·

2026/03/26

The build versus buy decision is becoming more critical as AI agents enter the enterprise. This episode explores why understanding what you’re buying, how it integrates, and who owns it is essential before making a commitment. The focus is on maintaining control, reducing risk, and making informed decisions that actually support the business. Watch the full episode here: https://youtu.be/RZnuL2aEU1Y Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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4:55

Should You Invest in AI Agents?

ByteSized ·

2026/03/25

Many organizations rush into AI without defining what they actually need it to do. This episode explores why starting with the problem leads to better outcomes than chasing trends. The focus is on making disciplined, value-driven technology decisions.Watch the full episode here: https://youtu.be/RZnuL2aEU1Y 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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2:50

New Systems Don’t Fix Broken Processes

ByteSized ·

2026/03/24

Many organizations blame their technology when the real issue is how they operate. This episode explores why poor processes, lack of structure, and unclear ownership are often the root problem. Fix the foundation before investing in something new.Watch the full episode here: https://youtube.com/live/EJ03W5KNxh0 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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4:20

Are You Replacing Systems Before Understanding the...

ByteSized ·

2026/03/23

Many organizations rush into new systems without fully understanding what’s actually broken. This episode explores why slowing down, involving frontline teams, and evaluating current tools often leads to better outcomes. Before replacing anything, the focus should be on solving the right problem and getting more value from what already exists. Watch the full episode here: https://youtube.com/live/EJ03W5KNxh0 Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on

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4:20

Are You Solving the Right Problem Before Replacing...

ByteSized ·

2026/03/20

Too many organizations rush into new systems without fully understanding the root problem. This episode explores why slowing down, listening to frontline users, and evaluating existing tools often leads to better outcomes. Before replacing anything, the focus should be on using what already works more effectively and aligning solutions to real business needs.Watch the full episode here: https://youtube.com/live/EJ03W5KNxh0 Connect with me on LinkedIn

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4:22

What Value Should You Actually Expect from AI?

ByteSized ·

2026/03/19

AI does not create value on its own. It should enable a clear strategic objective defined by the business. This episode explores how to set expectations for AI investments, what outcomes should be contractually aligned, and why vendor roadmaps and legacy system sunsetting have more to do with their business model than your success.Watch the full episode here: https://youtube.com/live/EJ03W5KNxh0 Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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1:45

Are You Blaming the Wrong Thing in Your Legacy System?

ByteSized ·

2026/03/18

One of the biggest mistakes organizations make when evaluating legacy systems is assuming the technology is the limitation. This episode explores how people, processes, and policies often create the real constraints, and why replacing software without addressing those issues leads to the same problems in a new system.Watch the full episode here: https://youtube.com/live/EJ03W5KNxh0 Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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5:22

What Are the True Costs of Replacing Your Legacy...

ByteSized ·

2026/03/17

Infrastructure is only one piece of the cost equation. This episode breaks down how operational complexity and people impact the true cost of system decisions, from internal resource strain and burnout to the risks of replacing systems that already work. The focus is on evaluating tradeoffs realistically and understanding what your organization can sustain before making a change.Watch the full episode here: https://youtube.com/live/EJ03W5KNxh0 Connect with me on LinkedIn

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2:41

When Is It Time to Move On From a Legacy System?

ByteSized ·

2026/03/16

Companies often hold on to legacy systems longer than they should, but the real question is not age. It is capability. This episode explores how to recognize when a system is preventing strategic growth, why the software itself is not always the problem, and how to evaluate when adding or changing systems becomes necessary. Watch the full episode here: https://youtube.com/live/EJ03W5KNxh0 Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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2:41

How Should Maintenance Data Shape Production Planning?

ByteSized ·

2026/03/13

Maintenance data can dramatically improve production planning, but only if the data is trustworthy. This episode explores how predictive maintenance, machine sensors, and operational expertise should inform reliability decisions, while emphasizing the importance of validating data before relying on it to guide production strategy.Watch the full episode here: https://youtube.com/live/V64qoIrPdAQ Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram

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131 results

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