Skip a step: bring someone technical to the first demo
After noting a pattern of sales reps crying "uncle” at my questions and scheduling a 2nd demo with someone technical, I’ve started requesting that up front. Most salespeople cannot handle me, especially once I steer them off-script into the Setup screens where the interesting bits actually live.
I get it, the technical side of things is not their job, their job is to say whatever makes executives open their wallet. Alright, I’m being harsh, but y'all smell the bulbous grain of truth in there.
A polished front end is part of the equation, but I want to see more than just the parts that are dressed up as AI chatbots. Show me the guts: how things are configured, the properties modals, the API documentation, the DevOps pipeline. Tell me the limitations... I'm so good at hitting limitations in software, you should just fess up now.
What I’m really trying to ascertain is whether your solution actually meets the needs of the organization I’m representing. I want to know if it’s going to be a hassle to configure or integrate, and how much my client will end up relying on me to cover the gaps the sales team never mentions. Bring someone technical who can handle that conversation with integrity, and if your product actually walks the walk, you'll gain a consultant out there singing your praises.
Jessie Grenfell
Jessie has spent 20+ years architecting and delivering software for organizations where complexity is the norm — financial services, insurance, nonprofits, and regulated industries where getting it wrong isn't an option. She specializes in the hard problems: unique operational workflows, cross-system integrations, and the kind of compliance requirements (HIPAA, CCPA, SOC 2) that most developers treat as someone else's job.
At Codality, she leads every principal engagement from discovery through delivery — because she's seen what happens when that thread gets cut.