Questions to Ask Yourself Before Buying Your Next Licensing Solution
Introduction
It can’t be stressed enough how much the Customer Experience matters when it comes to Software Licensing.
We constantly talk with companies who have seen up to 60% of their Support Tickets be down to Licensing issues, difficulties and misunderstandings. ALL of these represent frustrated customers - you want happy customers not frustrated ones, right?
So…
Ask: What takes end users more than 10 seconds today?
Does an end user have to perform licensing tasks all over again when license rights change due to a renewal of a subscription, purchase of add-on features or additional seats?
Licensing Strategy and Implementation
Do they have to take a license file and stick it in an obscure location in the file system?
Are customers having to be pointlessly exposed to complicated and arcane concepts — MAC addresses, “Host IDs” or server names?
Ask: What advantages does the latest licensing technology bring?
Does it support friction-free licensing that gets you and your customers up and running quickly?
Licensing Strategy and Implementation and Next Steps
Will it eliminate users dealing with excessive details and confusing jargon?
Will it enable you to build customer-centric licensing focused on a great end user experience?
Does it make it far easier for customers to upgrade, renew, rehost and view their entitlements, resulting in less customer support overhead and higher customer satisfaction?
→Conclusion
Ask: How easy would it be to migrate to a new system?
How does a new solution support mass migration of your existing entitlements?
Is silent activation functionality offered so a change requires “zero touch” for customers?
Does the vendor have success with transitioning clients from legacy environments to a new system?
About the Author
Jon Gillespie-Brown is the Founder and CEO of Nalpeiron, a leader in cloud-based software licensing, entitlement management, software monetization, and analytics. With over 20 years of expertise, he works with enterprise B2B SaaS and IoT companies to optimize revenue models, accelerate go-to-market strategies, and scale with confidence. Jon is recognized as an authority in software licensing, software monetization, and software analytics, holds two issued U.S. patents, and is the author of five books. He also serves as a strategic guide to customers, helping them navigate and capitalize on the once-in-a-generation shift driven by AI, redefining how software is built, delivered, and monetized. For over 20 years, Jon has been a Professor at University of Colorado Boulder, a lecturer at University of California, Berkeley and Stanford University, and an Entrepreneur in Residence at London Business School.
Nalpeiron: A Long-Term Partner for the AI Era
At Nalpeiron, we go beyond technology — we act as a strategic partner in licensing, monetization, and growth. For over twenty years, enterprise and IoT companies have trusted us to guide and evolve their business models.
As AI shifts software from seats to usage, outcomes, and agent-driven activity, legacy approaches fall short. Nalpeiron enables this transition through entitlements as the control plane — a centralized system of record across SaaS, on-prem, IoT, and offline environments.
From strategy to execution, we help companies adapt faster, launch new models, and stay in control — making Nalpeiron a partner for the AI-driven future of software monetization.
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