Navigating Government Procurement and the Future of CAMA Software with Tony Henderson

Tony Henderson has been in the property tax assessment industry for 33 years and attending IAAO conferences for 43 — since his father took office as a county assessor in Kentucky in 1978. He started as a field appraiser for CLT, moved into sales with CLT and Tyler, and has now launched Baseline Advisory Consulting to help jurisdictions navigate the full lifecycle of CAMA and tax software procurement. In this conversation recorded at IAAO 2026, Tony makes a deceptively simple argument: most jurisdictions are making generational technology decisions with inadequate preparation, and the way RFPs are currently structured almost guarantees mediocre outcomes.

The Generational Buy Problem

Tony frames CAMA and tax system purchases as "generational buys" — decisions that will shape how a jurisdiction collects revenue for 15 years or more. And yet the people making these decisions often have almost no experience doing so. An assessor might purchase one enterprise system in their entire career. Two, at most. The price they paid for their legacy system is from a different era entirely — it's not comparable to what the market looks like today.

This inexperience creates a gravitational pull toward the familiar. Institutional knowledge gets deeply embedded in existing systems. Staff develop workarounds rather than demanding better tools. The risk of switching feels enormous, especially when conversion costs loom large. The result is a cycle of vendor lock-in that doesn't serve the taxpayer particularly well. Tony doesn't say this with any malice toward the vendors — he spent decades on that side of the table. He simply observes that the structure of procurement itself tends to reinforce the status quo.

The Feature Function Trap

One of Tony's sharpest observations is what he calls the "feature function trap." Most RFPs are structured so vendors can check yes to hundreds or even thousands of line items. Many of those RFPs are borrowed drafts from other jurisdictions, with requirements that may not even be applicable. The weighting across features tends to be flat — core functions that actually drive success aren't prioritized over minor capabilities that rarely matter in practice.

The result is predictable: every vendor scores similarly, and the jurisdiction hasn't actually learned what it needs to know. Tony argues that the real insights come from asking harder, scenario-based questions. What happens when significant legislative changes hit two years into implementation? How does that affect your timeline, your conversion, your training plan? Pressing vendors on real-world contingencies reveals far more about their actual capabilities than a thousand yes/no checkboxes ever will.

Start Early or Get Surprised

When asked what's most underrated in CAMA procurement, Tony's answer is straightforward: doing your homework early. If you're planning a 2028 or 2029 implementation, you should already be meeting with the vendor community in late 2026 and 2027. Not in a formal procurement context — informally, to understand the playing field.

This pre-RFP period is where jurisdictions can actually learn what's available without being bound by strict procurement rules that limit conversation. They can check references, see demonstrations, and understand what's changed in the market since their last purchase. Tony sees too many offices doing this work late or not at all, then getting blindsided when proposals come in. The RFP itself is not the process — it's just one artifact within a much longer journey that should start with a genuine needs analysis.

AI Changes the Equation

The conversation takes an interesting turn when the discussion shifts to large language models and what they mean for the future of CAMA software. Tony acknowledges he doesn't personally use these tools for building solutions, but he recognizes the implications. Software development is getting dramatically cheaper and faster. The traditional heavy lift of modifications, support channels, and configuration could be radically simplified.

Tony sees the real challenge not as a technology problem but as a description problem. Can a jurisdiction clearly articulate what it needs? That's where institutional knowledge — deep, applicable experience in assessment and taxation — becomes irreplaceable. The models can build whatever you need, but only if someone who truly understands the domain can describe the problem with precision. This is actually a strong argument for Tony's own consulting model: smaller teams with deep domain expertise, positioned between the jurisdiction and the technology, translating real operational needs into actionable specifications.

Vendor Presentations Need to Evolve

Tony also takes aim at how vendor presentations have stagnated. In his experience, they haven't meaningfully changed in 20 years. Vendors get a script, walk through the same checkboxes from their proposal, and the jurisdiction doesn't learn much beyond what was already on paper. If procurement rules are interpreted too strictly, the presentations become performative rather than informative. Tony advocates for working with jurisdictions to design presentations that actually surface useful information — not just confirm what's already been submitted.

Key Takeaway

The biggest risk in CAMA procurement isn't choosing the wrong vendor — it's never giving yourself the chance to make a truly informed choice. Tony Henderson's core message is that the real work happens before the RFP drops, and jurisdictions that treat procurement as a months-long learning process rather than a document exercise will make decisions that serve their communities for the next generation.