Q&A With Uptime Legal Systems Founder & CEO Dennis Dimka

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Dennis Dimka

Dennis Dimka, Founder & CEO, Uptime Legal Systems

If you’re not familiar with Dennis Dimka and his Eden Prairie “Law Firm as a Service” Uptime Legal Systems, you should be now. They were ranked #2,010 on the 2014 Inc. 5,000 list with $2.7m revenue and again #2,033 in 2015 with $4.15m top line revenue.

With consistent double-digit year over year growth, healthy margins and profitability — the company just acquired New York-based JurisPage while Dimka was also recently nominated as a 2016 EY Upper-Midwest Entrepreneur of the Year Finalist.  Let’s learn more about Uptime’s success in the making:


When, how, and why did you startup Uptime Legal Systems?

I started the company by myself just over ten years ago. Initially known simply as Uptime Systems, we began as a classic managed services provider (MSP) consulting firm in 2005. Four years later we got into the hosting business, and after four years of doing that, we decided to throw down the gauntlet into one arena: the legal sector.

In around 2012 we went through a top to bottom remodel of the company — the name, the brand, the software, the team — everything became new again under the name Uptime Legal Systems.

What were you doing before this that lead to Uptime?

I was an IT/Network administrator for a local company in Eagan.  It was through that experience that I was exposed to outsourced IT and took a close look at that model as a way for me to start doing my own thing more independently.

Why did you decide to move Uptime specifically into the legal industry?

I think before I can answer why legal, how about why verticalized? The answer there is that it’s the best way to stand out and grow as IT services become more and more commoditized.

It was both exciting and scary to think about going all in on any one industry because you’re essentially closing the door on the rest, that is the trade-off of specialization.  But in doing so, the conversation is focused more around value than around price.

So why legal as the direction? Because we had a lot of clients already in the industry and experience in hosting and supporting specific applications often used in the space. That was naturally a core demographic we already served. From a technical perspective, they are always on the go, their need for data security is arguably higher than other industries and lastly, they don’t have time for IT issues.

So when we looked at our current customer segment and strengths in mobility, security and reliability, it all just added up!

So what did you start to offer them beyond hosting?

Uptime Practice, was and remains our core product — a securely hosted, private IT environment. We knew that would eventually become highly competitive and commoditized so we developed our own true IP, LegalWorks, a SaaS solution for lawyers to manage their email and documents.  And now, as you know, we purchased JurisPage earlier this month which we are in the middle of integrating into the business.

How and why JurisPage?

We met JurisPage a number of years ago and immediately respected their work.  Their team of five will stay in Manhattan and we plan to grow the team and footprint there.  The two founders will stay on, and Andrew Cabasso will transition into the head of marketing for Uptime across the board. We’ll essentially keep our headquarters here in Eden Prairie and that will be our second location.

How many in Eden Prairie and what roles?

We have 18 employees now; three executives including myself, two account managers, one admin, and everyone else is technical in nature.

How do you hire?

We’ve tried everything — from Monster and Dice to Craigslist. Our vetting is constantly being refined but we have created a streamlined process that seems to be working for us.

Did you bootstrap to where you are today or are there other investors/partner(s)?

I am the only company owner, and have not taken any outside investments, self funded to date. Of course we wouldn’t be here today without our team and would like to recocgnize my number 2 — Aaron Eittreim, Chief Business Development Officer, and Erin Pickar, who joined as an admin/assistant and is now our Chief Operating Officer.

How do you market and sell the products?

The number one means is online advertising, believe it or not. We’ve spent years perfecting our formula for AdWords, which is very effective now. Second would be relationships with leading software publishers like LexusNexus, WestLaw, similar companies that make practice management software.

What is your big picture goal with the company?

To be the market leader in cloud services to law firms.

How do you plan to achieve that?

Organic growth is strong for us and we’ll continue to focus on that, while I wouldn’t rule out further acquisitions.

What other services or products do you see as part of that?

We’ll continue to look for ways to enrich our portfolio, but I need to be aware of the drawbacks of business ADD.  What do law firms need and where is there tonnage from our perspective? That’s our guiding criteria.

Why did you trade mark “Law Practice as a Service”?

There’s so much talk about ‘as a service’, I thought that would click…the jury is still out.

What do you attribute your success to so far?

Going vertical, without a doubt, had a huge positive impact on us. From there, starting to think and act nationally.

About how many customers do you have?

Close to 400 law firms that range in size from a couple employees to 50+ in North America, that’s our sweet spot where we demonstrate the most value.

What does the remainder of 2016 look like for you?

The big thing is integrating with JurisPage, beyond that growing the JurisPage offering and team with our current customer base.

Is there anything else you would like to add?

Thank you for the conversation and coverage!

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