Ollie Roby

Founder of Digitus Rain
SaaS Software - Legally Connected (Legal Firms)
SaaS Software - Flink (Training Software)

[Ollie Roby @ollieroby_]

Claude Fable seems like a big step forward - only after initial testing

[Ollie Roby @ollieroby_]

Everyone is asking how AI will replace jobs.
I think the better question is:
What repetitive tasks can AI remove so people can focus on more valuable work?

[Ollie Roby @ollieroby_]

In the software we build we always see process as the problem.

I’ll be using this account to share what I’m learning while building software companies, working with clients and implementing AI in the real world.

Just lessons, wins and mistakes.

[Ollie Roby @ollieroby_]

One thing I’ve learned from building software

The people closest to the problem often have the best solution.

Not the directors.

Not the consultants.

The person doing the task every single day.

That’s who we try to speak to before writing a single line of code.

[Ollie Roby @ollieroby_]

Most software projects don’t fail because of bad code.

They fail because nobody agreed what success looked like before development started.

The best developers I’ve worked with spend less time coding and more time understanding the problem.

[Ollie Roby @ollieroby_]

Every month spent building the wrong thing is a month not selling.

[Ollie Roby @ollieroby_]

Agencies need to stay flexible.

A spec written on day one rarely survives real-world usage unchanged. The best results come from working closely together and quick adaptation

[Ollie Roby @ollieroby_]

5 Signs Your Law Firm Has Outgrown Its Current Case Management System

https://t.co/HRp1DonxTL

[Ollie Roby @ollieroby_]

A lot of law/case firms are still running 1000's of cases on tools designed in 2005.

Case management software should be:
- simple
- auditable
- automated

https://t.co/Cs5XaveBHR

[Ollie Roby @ollieroby_]

@hunterhammonds Is it better to use than 2 displays?

[Ollie Roby @ollieroby_]

Most legal CRMs are bloated and ugly.
I am so excited building one that people actually like using.

[Ollie Roby @ollieroby_]

Just pushed:

- WhatsApp → CRM sync
- Triggers outbound replies
- Adds notes + files to case record

[Ollie Roby @ollieroby_]

An amazing use of AI through our software is to make it feel simple, yet behind the UI it is so complex, removing stress for users and freeing up real time!

[Ollie Roby @ollieroby_]

Payments now running smooth with

Stripe
Opayo
GoCardless
PayPal
Braintree

Next up @whop payments

[Ollie Roby @ollieroby_]

If your law or case management firm is still managing cases in Excel or an old-school CRM…

You’re losing days every week.

→ No audit trails
→ No RAG tracking
→ No automation

We built a system that fixes all of it.

[Ollie Roby @ollieroby_]

I can't believe it's taken me this long to add dark mode to our case management system

[Ollie Roby @ollieroby_]

We’re building something special for case management teams:

→ Track every case lifecycle
→ Custom workflows
→ Email/SMS/WhatsApp triggers
→ Full audit trail

It’s SaaS, but with real operational DNA

[Ollie Roby @ollieroby_]

If you are in the Legal sector, we are building Legally Connected to make managing cases feel so effortless!

[Ollie Roby @ollieroby_]

Building software is the most enjoyable and frustrating thing you can do!

[Ollie Roby @ollieroby_]

@hunterhammonds I'm in