Synapse SF brought together a room of senior tax and finance leaders who were willing to do something that doesn't happen often enough: stop and reflect honestly on where their functions actually sit today. Given the pace of change in the external environment, new e-invoicing mandates, countries revising how they tax cross-border services, AI moving faster than most teams have planned for, that kind of honest conversation has real value.

We ran a live tax technology maturity assessment during the session. Twenty-one respondents answered eleven scored questions across data foundation, tax determination, e-invoicing compliance, operational reality, and strategic positioning. The results were more revealing than I expected.

1. Nobody in the room had a single source of truth for tax data

Every respondent was working with fragmented data spread across multiple systems, each with its own format and owner. When that many people in one room share the same infrastructure picture, it stops being an individual problem and starts being a market condition.

The month-end fire drill that tax teams typically describe as a resourcing problem is almost always a data infrastructure problem that has never been clearly named as one. The downstream effect was consistent with the data picture: 91% found tax data errors at close or later, some during reconciliation and some during audit. Name the real problem first and everything else follows from it. 

2. 76% of respondents had invoicing compliance gaps

These were gaps where tax was being collected but compliant invoices weren't fully in place. Two-thirds of the room had launched in a new market in the last year, and almost none had invoicing compliance ready on day one.

The pattern is familiar: go-live pressure wins, compliance infrastructure follows later. The gap between launch and compliance readiness is where audit exposure accumulates quietly over time, and it rarely surfaces until a tax authority makes it urgent.

3. 94% of leaders expected their tax function to become advisory-led within five years

On the question of how much time goes to execution versus advising the business, not one person out of 17 respondents scored the top option. Everyone was spending the majority of their time on execution work.

Set against that, 94% said they expected their function to look fundamentally different in five years, with less execution, more strategy, and more direct involvement in business decisions. Both answers came from the same room, within 20 minutes of each other. The gap between those two data points is the most instructive thing in the dataset, and it isn't primarily a skills gap or an ambition gap. The teams that close it fastest are the ones that build infrastructure capable of running compliance execution without constant human intervention.

4. 88% had already had the AI conversation with their CFO

That conversation had happened in the last 90 days for the vast majority of the room, which tracks with what I hear across most of the organisations I work with. What surprised me was that a third of respondents hadn't yet worked out where their line was on AI autonomy. The pressure from leadership had arrived before the position had been formed.

That gap is worth closing before the next conversation. Agentic AI is moving from concept to reality: systems that don’t just answer questions but act, make sequential decisions, and execute tasks autonomously. As this happens, the teams without a clear position will find that position gets set for them. 

5. One business in the room had already achieved full end-to-end automation

This was the detail that stayed with me after the session. One organisation had reached full automation from extraction through to filing. What made it possible wasn't simply access to better technology. Their tax team had developed the technical skill set to own the infrastructure themselves, without dependency on engineering or a backlog. They built it, they run it, and they trust the output.

It was a simpler business model than most in the room, and it's worth being honest about that. But the more instructive point was what the blockers looked like for everyone else. For most of the organisations in that room, the gap wasn't ambition or budget. It was fragmented data and a team that hadn't been set up to own the infrastructure directly.

The common thread running through all five findings 

Look at findings one, two, three and five together, and a single pattern emerges. Fragmented data creates invoicing gaps. Invoicing gaps create compliance risk. Both keep teams stuck in execution mode. And the one business that achieved full automation did so because it solved the data layer first. The infrastructure problem and capacity problem are the same problem. Fixing one is how you fix the other. 

The honest baseline of tax technology maturity today

Nobody scored Aspirational. The bulk of respondents sat in the Progressing–Established band, which reflects the honest baseline of the mid-to-large enterprise tax function right now. The external environment has moved faster than the infrastructure most teams are running on, and that gap shows up clearly in the data

The first step to closing it is understanding precisely where you are and what the path forward looks like for your specific tech stack and jurisdictions.

Assess your own tax maturity 

Take the online tax technology maturity assessment to benchmark your own operations. It takes around six minutes and covers the core areas explored at Synapse SF, a shorter version of the full assessment that goes considerably deeper. Simply answer six questions to receive a customized report to help you understand where you currently stand and how to improve.