By Colby Cabral, VP of Accounting, Degreed
If you work in finance or procurement, you know the feeling: A major software renewal is coming up, and the platform is deeply embedded in the business. Everyone knows switching would be painful.
That dynamic can make renewals feel almost predetermined.
You review the terms, push back where you can, trying to limit increases. Maybe you get a little movement. Maybe you don’t. Either way, the process can start to feel more like a formality than a true evaluation of what the business needs and how well the technology is delivering it.
You’re not alone. Approximately 71% of businesses will stay with the same tech, software, or SaaS vendor even if they are dissatisfied, according to TechTarget.
Over the past year, as my role has become more connected to how finance supports procurement, I have started using Degreed Maestro (our AI that’s built for learning) differently. I had already used it for coaching, communication planning, and leadership situations. But as our vendor renewals loomed, I began using Maestro as a preparation partner for the procurement cycle itself. AI isn’t a replacement for human judgment and doesn’t do the work for me. It’s more like a coach sitting beside me, helping me think through the process before I have the renewal conversation.
Using Maestro Before the Vendor Conversation
In procurement, the first conversation with the vendor can set the tone for everything that follows. If you sound casual, the vendor may assume the renewal is routine and there’s no reason to adjust much. If you sound overly aggressive, you risk damaging a relationship that still matters. The balance is hard to strike, especially when you are not a professional negotiator and you also need to preserve a productive working relationship.
That is where Maestro helped. It didn’t give me the perfect script. It did something better: It helped me slow down and prepare before the conversation. I could explain the situation, describe the vendor relationship, share the business context, and ask it to help me shape the right message.
I could also use Maestro to help set the tone and narrative of the conversation. For example, I could ask it to think through the discussion using principles from negotiation and influence experts like Chris Voss, Robert Cialdini, or Robert Greene.
The point was not to turn the conversation into a negotiation seminar or make it feel overly tactical. It was to be more intentional about the psychology of the discussion, how the message would land, and where I needed to be firm without sounding combative. From there, I could ask Maestro both about what tone I should use and what to avoid saying, in addition to how I could make the conversation feel serious without making it feel hostile.
Practicing the Real Negotiation Conversation
If Maestro had just given me a script (like a generic LLM), it would have been too rigid and wouldn’t account for the other side of the conversation. Coaching and roleplays with Maestro gave me a place to practice more flexibly.
One of the biggest differences with Maestro was the ability to rehearse a full conversation. I used voice mode to talk through the scenario in a way that felt natural. I could pause, interrupt, restart and try different versions of the message. Maestro would respond, pause, and give me the space to make it feel like a real conversation with a manager.
Maestro helped me practice that rhythm. It helped me refine my speaking cadence, think about where to pause, and consider how my tone might land. I even asked it to add pause cues into a script, then used that script as a guide while I rehearsed again.
That made the real conversations feel more familiar. I hadn’t memorized every word, but I had already worked through the hard parts. I had heard myself speak the message out loud. I had pressure-tested the language and gotten direct feedback on how it was received. I had a clearer sense of what I wanted the vendor to hear and understand.
Aligning Finance and Procurement Priorities
We were trying to make sure each renewal started with the right question: What does the business need now and does the current agreement still match that value?
Procurement cycles usually involve several internal stakeholders. Finance may be focused on cost discipline. Business owners may be focused on continuity and service. Executives may be thinking about broader priorities like measurable business outcomes and AI transformation. IT is considering integration, data security, and how things fit into the tech stack. All are valid, but you need these priorities to show up as one consistent message to the vendor.
Maestro gave me a way to organize that message. I worked through the business rationale, the tone of the outreach, and the internal talking points before the conversation moved forward. It helped translate a complex situation into a clearer narrative that finance and procurement could use consistently.
This ensured every renewal didn’t feel like a confrontation.
Creating Better Renewal Outcomes
I’d used Maestro before for development plans, coaching, and career guidance, but this was the first time I’d used it to help create a real financial impact.
Across our broader procurement work, preparation with Maestro has contributed to meaningful savings. In some cases, those savings came from better pricing. In others, they came from improved terms, better use of services, or a clearer understanding of whether a vendor still fits what the business needs.
The common thread was not a single negotiation tactic. It was preparation.
Why this matters
I do not consider myself a master negotiator. I work in finance. I care about the business, the numbers and maintaining productive relationships with partners we may continue working with for a long time.
Maestro made this procurement cycle feel more thoughtful, instead of automated. It ensured the real negotiation conversation was not my first negotiation conversation.
For anyone in finance, procurement, or any function that works with vendor management, that is a big deal.
You may not need a dramatic negotiation strategy to improve procurement. You may just need a better way to prepare for the next important conversation. Maestro gave me that.
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