The art of the right tools at the right time

This might be the most written-about topic by any software vendor. I get it. You can look up “best practices” in seconds and write blog posts about it in minutes (or maybe less… hello ChatGPT). The column will inevitably boil down to some variation of: define clear objectives, research, scope, implement, train, etc.

But honestly? Building the right tech stack is more art than project management. And yes, this is your role.

Without naming names, I’ve seen it a lot. Some particular examples:

I was promised offline/online syncing from a major ERP vendor, a critical feature for a multinational company operating in rural Africa. After three sleepless nights of data migrations and a big launch fanfare, we discovered it didn’t work. Lightning storms in Rwanda kept disrupting local servers. The solution? Relocating entire teams across eight countries to places with better internet (and fewer storms).
I rolled out a billing system that I fought for, only to find that receivables didn’t balance with revenue when the accounting team closed the books. It took hours of spreadsheets to fix. They would never trust it.
I watched three HRIS systems get implemented and pulled within three years, each abandoned because candidates kept getting lost in byzantine hiring requirements.
I’ve been in screaming matches on both sides, both as a vendor and as a user, where threats were tossed around like grenades even though everyone knew they were stuck with each other.
And many, many byzantine CRMs…

But I’ve also seen plenty of wins: ERPs that aren’t hated, billing systems that actually improved customer experience, budgeting systems that worked, FP&A tools that provided true visibility, quick implementations that added immediate value.

This article isn’t about generic best practices; it’s about the art of building your tech stack. The tech stack that will enable you to become the 10x CFO. The tech stack that will enable your great operational model and continuous use of scenarios.

The Bullets

Don’t upgrade your tech stack without fully understanding your bottlenecks across the company, else you risk creating a dysfunctional “Tower of Babel”
Choose the right tech stack for the moment, not necessarily the most robust. Scaling doesn’t demand heavy systems, complicated processes do.
Dive in when you're ready. Leverage your peer networks to see what systems they use, dive into the weeds of the scoping calls to examine edge cases.

The specifics:

1. Know your own processes

Recognize why you are even looking for new software? Either your current system is a disaster, or you’ve hit a scaling wall. If you don’t have a specific reason… don’t do it. Choose your battles. Adding expensive software to a broken system only builds an expensive Tower of Babel. Before making any decisions:

Map out your systems. What tools are in place, and where are the gaps? Is the issue process-related or a true system limitation? How do these tools connect? Do you have a data warehouse, and how does it stitch everything together?
Look for small wins first. Can you fix the process without replacing the entire system?
Assess bottlenecks based on time. Where is your team losing the most hours? That’s where tech should step in.
Prioritize one major need at a time. Fixing everything at once leads to integration mismatches that are hard to diagnose.
Clean up your data. A messy dataset will wreck even the best system. Fix it before transitioning tools as you’ll gain valuable insights into your current processes.
Decide where key data should live. What belongs in the ERP vs. the CRM? Should data be stored line by line or as summaries? Define what must be pulled into each system.

Every “upgrade” creates tension between implementation effort and business value. Ensure you’re prioritizing the needs of the entire company, not just finance.

Tip: Before changing core processes, consider tools that aggregate and display data from multiple systems. These high-impact solutions provide visibility without requiring front-line retraining.

2. Know a good tech stack for the moment

You don’t need Netsuite for a five-person startup or an HRIS system for a team of three. However, if you're the only one in a 100 person company who can pull together a basic financial overview, it’s time for a change. To make the right call, assess:

Your team’s strengths. Do you need something simple, or does your team have the skill and desire to add onto their normal workloads for a far-off payout?
The company culture. Some tools are rigid but take an army to run them, while others are customizable but require higher levels of training. Which do you need?
Implementation time. A great tool that takes a year to roll out might be worse than a decent one that’s live in a month.
Need for scale. Will this tool scale with you, or will you be shopping for another one in two years? Sometimes shopping for another in two years is completely reasonable depending on the implementation.
Solutions, not perfection. No system is flawless. The goal is to solve your key pain points, not check every box.

It’s not about getting the best tool, it’s about getting the right tool for your business at this moment.

Tip: Companies can scale without complex tech. Before investing, look at ways to simplify your processes by adjusting pricing models, streamlining marketing, or switching to standardized billing cycles. Better operations can lead to less need for tech.

3. Talk to peers

Your LinkedIn network is incredibly valuable. Someone has gone through whatever upgrade you want to make recently, so ask them how they did it. Key questions to ask:

What do you wish worked better? No tool is perfect and what are the pain points you are currently facing?
What was the biggest surprise post-implementation? User complexity? Missing features? Irreconcilable numbers?
Who actually uses it daily and how? This will help establish the structure of their team and how it might highly differ from your own.
How painful are manual workarounds? If the workaround takes hours per week, the system isn’t really saving time.
Who runs the system day-to-day? Some tools require a dedicated admin, find out before you buy.
Do you need an external consultant? Ideally not for anything that is a mid-sized implementation. You want to get up and running quickly and a third party can slow things down.

People are ready to talk about their experience as it often provides a release valve for things gone wrong.

Tip: Just ask anyone else you know in Finance. Somebody knows somebody. These networks are incredibly useful to see real-world impacts.

4. Get dirty in the scoping call

Yes, you can skip the initial meetings filled with PowerPoints and ‘mission control dashboards’. But you need to spend time having an in-detailed scoping call with your team and theirs to make sure it really works. Some tips:

Give the vendor a list of complicated transactions. Have them perform the transaction on the call. Imagine a new customer upsell that has to be reversed and seeing its impact on this month’s current deferred revenue recognition.
Have them set up a test version of your company. A real-world demo, not a generic walkthrough that uses as close to your data as possible.
Ideally, play around with it. Push buttons, see what breaks, see how well you truly understand how they imagine that you do things.
Bring in the actual users. The finance team, accounting, operations, sales, people, or whoever will touch this tool daily needs to be involved in the calls and/or demos. They will imagine edge cases you would miss.
Edge cases are everything. These are the hold-ups that will cause you to have complicated workarounds. Don’t ignore or sweep under the rug. Know what you are getting into.

Yes, this can be tedious but this is what matters, not just on the buying stage, but for knowing how you will implement it and how it will improve the company.

Tip: When you have a scenario, make sure that you are ready with audibles in the call so that you can see how the software can deal with real-world messiness.

5. Buy and implement

A system is only as good as you set it up to be. This is the time you get the most interaction and leverage with the vendor. So, use it! Get things as perfect as you can before going live.

Fix your processes before implementation. Software can’t clean up broken workflows.

Actively monitor implementation. Don’t assume the vendor will handle everything correctly, track progress closely, and engage as much of your team as possible in the process of setting things up.
Sanity-check full reports from both systems before go-live. Compare outputs between old and new systems to catch discrepancies that could need vendor support.
Train, test, repeat. If your team isn’t comfortable using the tool, they’ll find ways to work around it.

There is a lot more to this, but again, a lot of articles address this. Take time to ensure that your team is truly bought in before go-live.

Tip: People love being part of building something and stepping outside of their comfort zones. So, use that excitement to ensure later buy-in.

In conclusion

A best-in-class tech stack isn’t just for back-office teams; it sets the tone for how the entire company operates. If finance’s solution to everything is spreadsheet hell, the rest of the business suffers. If finance sets up best-in-class tools, decision-making speeds up and trust in the numbers improves.