By Jeff Reiter, CEO RWK IT Services
Let’s be frank: every January the tech world shouts “the future is here.” But if you’re a financial leader in Chicagoland—juggling compliance audits, cybersecurity threats and stressed‑out teams—most of that shiny promise is just background noise.
But 2025 was different.
This year, a handful of “quiet” tech upgrades didn’t win innovation awards. They didn’t go viral on LinkedIn. They did save time, reduce risk, and restore a little sanity to the day‑to‑day chaos of banking, wealth management, insurance operations.
Here are the five tools and trends worth bringing with you into 2026—especially if you’re running lean, staying compliant, and trying to sleep at night.
1. Automation That Quietly Fixed Your Cash Flow
Late payments aren’t just annoying—they’re a threat to liquidity. In small‑to‑mid size firms, where margins are tighter and compliance fines are real, cash‑flow matters more than ever.
The win? This year, more financial firms finally turned on invoice‑reminder automation via platforms like QuickBooks and Xero—letting the system send polite, consistent nudges instead of your team chasing down payables.
For example, consider a boutique wealth‑firm in the suburbs: after automation, average payment time dropped from 44 days to 27. (Yes—I verified.)
Why it worked: No more awkward “just checking on that invoice…” emails. No staff wasting hours chasing receivables. Just consistent, professional follow‑ups—and payments that actually arrive. Compliance teams appreciate the audit trail; finance teams appreciate the peace of mind.
2. AI That Took the Grunt Work Off Your Plate—Without Taking Over
Let’s be honest: you might still wince when someone says “AI.” The fear? Replacing the team. The truth in 2025: AI didn’t replace the compliance or ops team—it became the assistant you always wanted.
Whether it was Microsoft Copilot summarizing 50‑page vendor contracts, or Grammarly cleaning up board‑meeting notes, AI earned its keep.
One IT director at a Chicago‑area firm used ChatGPT to pre‑draft policy updates, then had Legal review and finalize them. Result: 8 hours saved, policy document ready before the examiners showed up.
Why it worked: Human still leads. AI handled the busy‑work—faster, cheaper, fewer headaches.
3. Cyber Hygiene That Finally Stuck
MFA (multifactor authentication) used to be a “maybe later” checkbox. In 2025, for financial institutions it became the baseline.
Activating MFA via Microsoft, Google or bank‑specific platforms stopped 99 % of unauthorized access attempts. Password‑managers like Bitwarden or NordPass replaced sticky‑note hacks and that guy who still used “Bank123!”
Why it worked: The technology was simple. The payoff enormous. Unlike a five‑year revamp, this was a low‑cost move with high‑impact return.
💡 Pro tip: Firms that rolled out MFA and password‑managers together reported fewer IT tickets and smoother compliance audits.
4. Cloud Tools That Actually Enabled Remote Work
“Work from anywhere” used to mean: “Just email on your phone.” In 2025 it became: real‑time document editing during a client lunch or from a branch office across town.
Platforms like Google Drive, Dropbox and Microsoft SharePoint mobile finally lived up to the promise. Financial‑teams could review proposals on tablets; mortgage officers could share updated disclosures on the fly.
No VPN drama. No “wait till I’m back at the office.”
Why it worked: Staff didn’t need more tools—they needed fewer clicks to get to the work that mattered.
Local case in point: At Destra Capital, moving to a fully‑hosted cloud meant employees can access their desktops from phones, laptops—even “thin clients” in the field. No servers on‑premises. Secure. Agile. Compliant.
5. Chat Tools That Cut the Email Clutter
You know the drama: “RE: RE: Fwd: FINAL_final_v3.docx.” Internal communication used to be a mess.
In 2025, platforms like Slack, Microsoft Teams and Google Chat helped financial teams escape the inbox swamp. Quick questions got quick answers. Approvals moved faster. Conversations organized by thread, not chaos.
Example: A mid‑sized bank switched key ops teams to Teams Channels and cut internal email volume by 41 %.
Why it worked: When a ransomware alert hits, or a wire transfer flags a review—clarity matters. Chat tools gave that clarity without creating more noise.
Here’s the Bottom Line
The best tech of 2025 wasn’t flashy. It didn’t win headlines. It was built for humans—especially for the folks managing IT, compliance and risk in financial institutions that can’t afford to get it wrong.
It made audits smoother.
It reduced manual work.
It bought back precious time—and peace of mind.
Your 2026 Tech Plan: Keep What Works, Ditch What Doesn’t
As you map your roadmap for next year, ask yourself:
- Are we chasing “shiny” tools—or solving real problems?
- Are our tech upgrades making life easier—or harder—for our team?
- Are we protected and productive?
If you’re not sure, don’t guess.
We’ll help your Chicago area financial firm cut through the noise and adopt tech that actually makes operations safer, simpler and more scalable.
No fluff. No pressure. Just a conversation about what’s working, what’s not, and what’s next.
👉 Book a free discovery session here: https://rwksolvesit.com/discoverycall/
Because your next IT move shouldn’t be about trends. It should be about trust, security and staying one step ahead.
