In this episode of Insights for IT Negotiations, hosts John Belden and Kylie Chisholm sit down with Jesse Webb, IT Director at SaskPower, to explore the story behind the utility’s highly successful SAP S/4HANA transformation.
Jesse shares the lessons learned from SaskPower’s multi-year modernization journey, from managing vendor costs and internal resource capacity to building a cohesive cross-functional team that ensured go-live readiness. She reveals how deliberate planning, risk mitigation, and strong collaboration between IT, business, and implementation partners helped the organization overcome early project hurdles and achieve a seamless go-live weekend.
Tune in to hear practical insights on:
Whether you’re preparing for your own SAP modernization or navigating a complex IT transformation, this conversation is packed with real-world lessons on what it takes to deliver results confidently and collaboratively.
Resources:
BLOG - Thriving Amid Uncertainty: How to Move Your Digital Transformation Forward While Others Freeze
BLOG - Rethinking Transformation Strategy in an AI-First World: AI is Changing SAP Strategy. Is Your Busin…
About the Show:
Welcome to Insights for IT Negotiations, a podcast by UpperEdge, a leading IT sourcing, negotiation, and project-execution advisory firm. Join John Belden, UpperEdge’s Chief Research & Strategy Officer, and Kylie Chisholm, UpperEdge’s Marketing Manager, every other week as they share high-impact insights to help you maximize the value of your key IT relationships.
Timestamps:03:05 — Overview of SaskPower and Its SAP Background
04:35 — The SAP Modernization Program
05:23 — From ECC to S/4HANA: Scope and Approach
07:03 — Modernizing Custom Applications and Risk Mitigation
08:33 — Lessons Learned from Earlier Projects
10:33 — Managing Internal Resource Capacity
13:20 — IT vs. Business Resource Constraints
14:05 — Business Integration and Dedicated Resources
14:39 — Sponsor Message (UpperEdge Subscription Advisory Services)
14:59 — Go-Live Readiness: Planning and Criteria
16:01 — Testing Strategy and Success Criteria
19:01 — Practice Conversions and Dress Rehearsals
20:04 — The Go-Live Weekend Experience
21:10 — Risk Management and Business Continuity Plans
22:53 — Lessons from Backup Planning
24:04 — Key Decisions That Drove Success
25:21 — Co-Location and Building Team Cohesion
27:08 — Value of Personal Relationships in Project Success
28:13 — What Jesse Would Do Differently
29:03 — The Importance of Context in Decision-Making
In this episode of Insights for IT Negotiations, host Kylie Chisholm is joined by Adam Mansfield, UpperEdge’s Salesforce Practice Leader, to unpack everything from Dreamforce 2025. They dive into how Salesforce’s Agentic Enterprise Licensing Agreement (AELA) is reshaping enterprise licensing, the emphasis on AI and “Agentforce,” and what all this means for you as a Salesforce customer approaching renewal.
Listeners will learn how to:
If you’re a Salesforce customer heading into renewal season, this episode offers timely, tactical advice to help you protect value and improve outcomes.
Resources:
VIDEO - Salesforce’s New Agentic Enterprise Licensing Agreement (AELA) – What Customers Need to Know
BLOG - Salesforce Increasing Pricing and Adding Agentforce Options: What Customers Need to Know Now
About the Show:
Welcome to Insights for IT Negotiations, a podcast by UpperEdge, a leading IT sourcing, negotiation, and project-execution advisory firm. Join John Belden, UpperEdge’s Chief Research & Strategy Officer, and Kylie Chisholm, UpperEdge’s Marketing Manager, every other week as they share high-impact insights to help you maximize the value of your key IT relationships.
In this episode of Insights for IT Negotiations, host Kylie Chisholm talks with Adam Mansfield, UpperEdge’s Salesforce Practice Advisory Leader, about how customers can successfully prepare for upcoming Salesforce renewals.
Adam discusses why many organizations are frustrated with Salesforce’s current direction, particularly its heavy focus on Agentforce and AI, while overlooking existing customer needs and product value. He explains what this means for enterprise buyers and how they can strengthen their negotiation position.
Listeners will learn how to:
If you’re a Salesforce customer heading into renewal season, this episode offers timely, practical advice to help you protect value and improve outcomes.
Resources:
BLOG – Salesforce’s New Agentforce Pricing: What Customers Should Know
VIDEO – Salesforce Q2 FY26 Earnings: Agentforce Hype vs. Reality
About the Show:
Welcome to Insights for IT Negotiations, a podcast by UpperEdge, a leading IT sourcing, negotiation, and project execution advisory firm. Join Adam Mansfield, UpperEdge’s Salesforce Practice Leader and Kylie Chisholm, UpperEdge’s Marketing Manager, every other week as they share valuable insights to help you maximize the value of your key IT relationships.
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
Oracle just named two co-CEOs and doubled down on an AI-first future. Jeff Lazarto explains how OCI’s gigawatt-scale GPU superclusters, Oracle’s vectorized “AI database,” and application-layer AI agents could make Oracle the standard for AI training and—soon—enterprise inferencing. He also highlights what this means for customers evaluating Oracle today: timing, deal leverage, and a practical path from on-prem to cloud/Fusion.
Key Points:
Episode Chapters
00:00:23 AI and OCI are driving Oracle’s momentum - Oracle’s earnings buzz is fueled by AI demand and OCI’s gigawatt-scale GPU superclusters selected by top AI players.
00:01:11 Why big tech is choosing OCI - Oracle claims faster/cheaper model training; efficiency and cost are key factors behind marquee customer selection.
00:02:04 Training now, inferencing next (the much bigger market) - Ellison frames inferencing—AI agents embedded in business processes—as the wave that will dwarf training.
00:02:46 From “college” to work: enterprise-tuned AI agents - Publicly trained models get fine-tuned on company data so AI agents can actually do tasks for the business.
00:03:05 Oracle’s AI Database and vector search - Oracle pitches a vectorized, privacy-preserving database that works across ~25+ models while keeping enterprise data secure.
00:03:41 Endorsement loop that benefits Oracle - If leading AI builders rely on OCI, enterprises may follow suit for hosting their own AI workloads.
00:04:24 OCI growth projections that shocked Wall Street - Oracle reiterated aggressive OCI revenue targets through FY30, a key driver of the stock’s surge.
00:05:12 Oracle’s stack: training → inferencing → data → apps - Strategy spans AI training/inferencing, the AI database layer, and SaaS built on AI application generators.
00:05:50 App generators = networks of AI agents - Oracle describes SaaS evolving from hand-coded software to AI agents linked by workflows.
00:07:07 Multicloud and “Cloud@Customer” options - Run Oracle in public regions, behind your firewall, or access Oracle Database from Azure/AWS/GCP via reseller arrangements.
00:07:28 Leadership shift: two new co-CEOs - Clay Magouyrk (OCI/engineering) and Mike Sicilia (industries/apps) step in; tech-first leaders for infra and apps.
00:08:05 Clay McGuirk’s remit (Gen2 OCI & AI DCs) - Architect behind high-performance OCI powering gigawatt-scale AI training is elevated.
00:08:30 Mike Sicilia’s remit (vertical apps & AI) - Industry SaaS leader focuses on applying AI within Oracle’s application portfolio.
00:09:12 Why tech visionaries at the top matters - Oracle follows the big-tech pattern: product-minded leaders setting direction vs. sales-led stewardship.
00:10:01 Co-CEO model returns; wider exec moves - Safra Catz shifts to executive vice chair; additional sales/finance leadership changes are in motion.
00:11:30 Two-engine company, two tech CEOs - Structure mirrors Oracle’s dual identity: infrastructure and applications led by AI-savvy chiefs.
00:11:57 Customer takeaway: leverage the moment - High expectations on Oracle create room to negotiate strong terms and strategic commitments.
00:12:44 Installed base path to AI value - Benefits of AI live in the cloud: Fusion for apps and OCI for tech; BYOL eases the move.
00:13:24 Expect harder Oracle push to cloud - Stronger GTM motions will highlight concrete AI/business value to drive migrations.
00:14:09 Start with your Oracle strategy, then engage - Define the enterprise roadmap first; invite Oracle to align capabilities and structure the right deal.
SaaS vendors often push programmatic renewal price increases—whether you used the product’s features (new or existing) or not. Here’s a fairer, customer-focused approach: only permit price hikes at renewal when (1) the SaaS vendor enhanced the production being subscribed to since your last renewal and (2) you’re actually using those enhancements. That aligns spend to delivered value and incentivizes vendors add enhancements of value and put in effort to help drive adoption.
Key points
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
In this episode of Insights for IT Negotiations, UpperEdge’s Adam Mansfield joins to break down Microsoft’s recent announcement to eliminate Enterprise Agreement (EA) volume discounts starting November 1st. Adam explains what this change means for enterprise customers, how executives are reacting, and the strategies organizations can use to prepare. From executive-level conversations to utilization analysis, alternative solutions, and the role of Cloud Solution Providers (CSPs), this discussion provides practical guidance for navigating Microsoft’s evolving pricing model.
Resources:
UPCOMING WEBINAR - Breaking the Microsoft Mold: How to Negotiate on Your Terms
BLOG - Microsoft Ends EA Volume Discounts: What It Means and How to Respond
VIDEO - Microsoft Ends EA Volume Discounts – What It Means for You
About the Show:Welcome to Insights for IT Negotiations, a podcast by UpperEdge, a leading IT sourcing, negotiation, and project execution advisory firm. Join John Belden, UpperEdge’s Chief Research and Strategy Officer, and Kylie Chisholm, UpperEdge’s Marketing Manager, every other week as they share valuable insights to help you maximize the value of your key IT relationships.
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
In this episode, Adam Mansfield, Salesforce Practice Leader at UpperEdge and industry expect, explains what the new Pay-As-You-Go and Pre-Commit, and Pre-Purchase pricing models mean for enterprise customers and why Salesforce is providing them.
Key takeaways and what will be covered:
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
Effective November 1, 2025, Microsoft will eliminate EA volume-based discounts for online services like Microsoft 365 and Dynamics 365. Adam Mansfield, Microsoft Practice Leader at UpperEdge, breaks down the impact, why Microsoft is making this change, and how enterprise customers can push back. Learn how this move ties to Microsoft’s motivation to accelerate ARPU growth, increased product adoption and upgrades (Microsoft 365 Copilot, E5), and shift more customers towards an MCA-E or CSP contracting model—and what actions need to be take right now.
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
Microsoft closed FY25 with strong revenue growth, fueled by Copilot adoption, E5 momentum, and Azure’s breakout 39% growth. Adam Mansfield, Microsoft Practice Leader at UpperEdge, breaks down the key takeaways from the earnings call, including what the numbers mean for enterprise customers with upcoming renewals or considering in-term purchases. Learn how Microsoft’s focus on moving customers to E5, AI (M365 Copilot, GitHub Copilot, Copilot Studio…etc.) will shape pricing, commitments, and negotiation leverage in the year ahead.
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
In this episode of Insights for IT Negotiations, UpperEdge’s Ryan McGhee joins John Belden and Kylie Chisholm to explore how generative AI is influencing SAP S/4HANA brownfield transformations. From productivity claims and risk mitigation to transparency challenges and use case development, the conversation uncovers what IT leaders need to know before engaging their system integrators. Learn how to separate hype from value, ask the right questions, and prepare your environment to fully leverage AI’s potential without sacrificing control or incurring hidden costs.
Resources
BLOG - Brownfield and the AI Gap: What Your SI Isn’t Telling You and Why It’s More Complex Than It Looks
Want to go deeper? Contact us to discuss how we can support your transformation strategy.
Salesforce is making bold changes that every customer needs to pay attention to. In this episode of Insights for IT Negotiations, UpperEdge’s Adam Mansfield joins Kylie Chisholm to unpack the upcoming 6% price increase, the evolving AgentForce pricing models, and Slack’s shift toward higher-cost enterprise editions.
They explore what’s really driving these updates, how they impact your current agreements, and what actions you should take now to maintain leverage, especially with Dreamforce around the corner.
Key Topics:
Resources
PODCAST – Salesforce Announces August Price Hikes & New AgentForce & Slack Plans: Here’s What You Must Do Now
BLOG - Salesforce Increasing Pricing and Adding Agentforce Options: What Customers Need to Know Now
If you’re a Salesforce customer, these changes are coming. This episode will help you get ahead of them. Learn more about how UpperEdge can help here.
Salesforce just announced a 6% price increase effective August 1st (20% for Slack Business+), alongside new Agentforce and Slack plans. This includes a staggering $125/user/month Agentforce add-on and an Agenforce 1 Edition for $550/user/month.
In this episode, Adam Mansfield, Salesforce Practice Leader at UpperEdge, breaks down the real strategy behind these moves and what Salesforce customers must do now to prepare before they get locked into higher costs without the right protections.
Key Takeaways:
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
In this episode of Insights for IT Negotiations, UpperEdge’s Adam Mansfield joins Kylie Chisholm to unpack the evolving reality of vendor lock-in in the cloud era and how AI is deepening that entrenchment. From the long-standing SaaS model to today’s rapidly spreading AI offerings from Microsoft, Salesforce, and others, organizations are finding themselves more tightly bound to vendors than ever before. But does that mean you're powerless? Hardly. Learn actionable strategies to mitigate the risks of cloud and AI lock-in, reframe your negotiation mindset, and hold vendors accountable for delivering long-term value.
Resources:
BLOG: How to Avoid Vendor Lock-in with Cloud Subscription Agreements
BLOG: Key Trends Disrupting Your Cloud Vendor Relationships
About the Show:
Welcome to Insights for IT Negotiations, a podcast by UpperEdge, a leading IT sourcing, negotiation, and project execution advisory firm. Join John Belden, UpperEdge’s Chief Research and Strategy Officer, and Kylie Chisholm, UpperEdge’s Marketing Manager, every other week as they share valuable insights to help you maximize the value of your key IT relationships.
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
Jeff Lazarto, Oracle Practice Leader at UpperEdge, breaks down Oracle’s explosive FY25 earnings, the role of AI in their growth, and strategic guidance for existing and prospective Oracle customers. From cloud infrastructure to database demand and Oracle’s aggressive sales posture, this episode unpacks what buyers need to know now to negotiate smartly and plan for the future.For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
Microsoft’s mega deal is raising big questions. A report suggests Microsoft is working on a 1 million-seat Microsoft 365 Copilot deal, but what does that actually mean for customers?
In this episode, Adam Mansfield, Advisory Practice Leader at UpperEdge, dissects the potential Microsoft 365 Copilot mega-deal and raises critical questions about possible and likely “over licensing,” the adequacy of discounting and pricing protections, and the potential shift toward consumption-based pricing.
If you’re evaluating Microsoft’s AI offering “Microsoft 365Copilot,” to any degree and magnitude, this is a must-watch.
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
Topics include:
There has been speculation that Microsoft is going to one day introduce a Microsoft 365 E7 plan. Adam Mansfield, Advisory Practice Leader at UpperEdge, shares his take on whether Microsoft 365 E7 is coming and why customers shouldn’t wait around for it. He breaks down the math behind M365 E3, M365 E5, and M365 Copilot pricing, the pitfalls of bundling, and why now is the time to focus on getting the right protections, flexibility, and pricing for your current Microsoft stack.
In this episode, learn:
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
In this episode of Insights for IT Negotiations, Jeff Lazarto and Shane Griffin pull back the curtain on a recent Oracle ERP transformation engagement. They share how a client secured over $11 million in savings and achieved long-term pricing protections without turning negotiations adversarial. Tune in to learn how UpperEdge’s relationship-based approach, proven negotiation strategy, and commercial term frameworks enabled an impactful outcome, and what other organizations can take away as they evaluate enterprise applications like Oracle and Workday.
Resources:
PODCAST - Mastering Oracle Negotiations: Insights from UpperEdge’s Expert Advisors
BLOG - Oracle’s Data Breach Response: A Crisis Management Playbook
About the Show:
Welcome to Insights for IT Negotiations, a podcast by UpperEdge, a leading IT sourcing, negotiation, and project execution advisory firm. Join John Belden, UpperEdge’s Chief Research and Strategy Officer, and Kylie Chisholm, UpperEdge’s Marketing Manager, every other week as they share valuable insights to help you maximize the value of your key IT relationships.
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
In this episode, Jeff Lazarto, Workday Practice Leader at UpperEdge, breaks down Workday’s Q1 FY26 earnings and what they reveal about the company’s direction—and how enterprise customers should respond.
With 13% YoY growth, major investments in AI agents, and the rollout of Workday Go for rapid deployments, Workday is pushing innovation and reach across sectors and geographies. But Jeff cautions: if you're expanding your Workday footprint, use this as an inflection point to revisit your contracts and pricing.
Topics include:
Salesforce just released its Q1 FY26 earnings, and it’s clear: Agentforce (Salesforce’s AI offering), and Data Cloud are at the heart of its future growth strategy. In this episode, Adam Mansfield, Advisory Practice Leader at UpperEdge, unpacks the financials and the implications for current and future Salesforce customers.
From 8000 Agentforce customers (1/2 paying customers) to CEO, Marc Benioff’s vision to make all customers AI + DATA + CRM” customers, Adam explains what you need to do now to lock down pricing, define terms, and protect against the coming consumption push.
Highlights include:
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.
In this episode, Adam Mansfield, Advisory Practice Leader at UpperEdge, analyzes key messages from ServiceNow’s recent Financial Analyst Day and what has been revealed to ServiceNow customers, including ServiceNow’s clear focus on accelerating AI revenue growth and getting customers to upgrade. He also discusses what that means for customers moving forward.
ServiceNow is aiming to grow its AI-related revenue from $250M to $1B by FY26, largely by pushing customers to upgrade to Pro Plus (Pro+) through “low cost” starter packs, steep uplifts, and vendor friendly hybrid pricing models that include a consumption based pricing component.
Adam outlines:
For more innovative IT sourcing and risk mitigation insights, subscribe to the UpperEdge newsletter and follow UpperEdge on LinkedIn and Twitter.