From Risk to Reward: How SaskPower Achieved a Smooth S/4HANA Go-Live with Jesse Webb

Insights for IT Negotiations

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:

• Balancing internal and external project resources
• Establishing clear go-live criteria and risk mitigation plans
• The power of co-location and building team trust
• How early alignment and executive communication drive project success

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:

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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