Law firms face no shortage of technology providers. But finding a partner that truly understands their industry — and evolves with their needs — is rare.
That’s exactly what Uptime Legal set out to change.
What began as a solo IT consultancy has grown into one of North America’s leading legal tech companies, serving thousands of law firms with cloud, DMS, IT, and digital marketing solutions. This is the story of how Uptime Legal was built—from humble beginnings to industry leader.
A Simple Idea with Big Potential
Uptime Legal started with a practical vision: do meaningful work, independently, and earn a living doing it. Dennis Dimka, Uptime’s Founder and CEO, launched the company after realizing he could offer the same value as expensive IT consultants — at a fraction of the price and with greater care.
Operating under the name Uptime Systems, Dennis ran a one-man show — supporting businesses, closing deals, handling admin, and delivering service. But when first-year revenue exceeded his projections, the light bulb went off. This wasn’t just a solo consultancy. It had the potential to scale.
From Solo Practice to Growing Team
As the business grew, so did the need for support. Dennis brought on longtime friend Aaron Eittreim — now EVP of Sales — to help with both service delivery and business development. Soon after, Erin Pickar joined as a part-time admin. Over time, she took on more responsibilities, rising through the company to become Uptime’s President & COO.
The first office was modest: 1,500 square feet, glass-walled rooms, and a tech-forward, open-concept vibe. It may have been small, but it held big dreams — and laid the groundwork for a much larger organization.
The Turning Point: Focus and Differentiation
Early on, Dennis faced the same challenge every founder does: wearing every hat. From marketing and tech to bookkeeping and client service, the demand was relentless. Long days were the norm.
The real turning point came when Uptime made a strategic shift to specialize.
Instead of trying to serve everyone, Uptime focused on three key areas:
- Specialization in cloud technology
- Verticalization into the legal industry
- Productization of services to simplify buying and scaling
That SVP strategy — Specialize, Verticalize, Productize — transformed the company. Growth accelerated, and Uptime quickly emerged as a go-to legal tech partner.
Key Milestones That Shaped the Journey
Over the years, Uptime Legal has reached major milestones that redefined its scope and impact:
- 2016 – Acquired JurisPage, expanding into legal website design and digital marketing
- 2017 – Began development of LexWorkplace, Uptime’s proprietary cloud DMS
- 2023 – Signed the first LexWorkplace Early Access client
- 2024 – Completed the largest acquisition to date: LexCloud Canada
- Ongoing – Team growth across three North American hub offices
- Leadership – Erin Pickar promoted to President & COO
Each milestone reflects a broader ambition: to become the all-in-one legal tech hub for modern law firms.
Building Products That Solve Real Problems
Every Uptime business line exists to solve a core challenge law firms face.
Uptime Practice
Traditionally, law firms purchased and maintained their own on-site servers — a model that was expensive, time-consuming, and difficult to scale. Uptime Practice reimagined that approach. Instead of owning hardware, firms access a secure, fully managed private cloud platform.
With Uptime Practice, firms get everything they need — legal software, file storage, remote access, and top-tier IT management — without the headaches of physical infrastructure. It’s scalable, predictable, and purpose-built for the legal industry.
JurisPage
Uptime recognized that most legal tech providers ignore growth strategy. By acquiring JurisPage, a legal-focused website and marketing agency, Uptime expanded its value proposition — helping firms not just manage tech, but also grow their practices online.
LexWorkplace
After years of frustration with clunky, outdated document management systems, Uptime built its own. LexWorkplace offers the power of a traditional DMS with the simplicity of Google Drive— designed for legal professionals, with security, compliance, and usability in mind.
Each product emerged from listening to firms, seeing where the industry fell short, and building something better.
Growing the Right Way: Team and Culture
Uptime’s growth hasn’t been limited to product lines. The team has scaled significantly, with more than 50 employees across two countries. But what stands out is the culture of development.
Dennis believes that a growing company demands growing leaders. Nearly every executive at Uptime has risen through the organization, evolving alongside it. That alignment between personal growth and business growth remains a key strength.
Uptime’s Role in the Legal Tech Ecosystem
The legal industry has undergone massive tech shifts over the past decade—most notably, the migration from on-premise to cloud-based systems.
Uptime Legal has not only kept up — it’s helped lead the change.
What makes Uptime unique is its hybrid structure. It’s part MSP/CSP — delivering service-rich cloud platforms — and part SaaS innovator, developing tools like LexWorkplace from the ground up.
Today, Uptime supports law firms in the U.S. and Canada with:
- Managed cloud IT
- Legal document management
- Software implementation
- Website and digital marketing
No other legal tech provider offers this breadth of support under one roof.
Core Values That Drive the Business
Uptime’s Core Values are more than just words — they’re the principles that shaped the company’s journey and continue to guide its future:
- Think Big
- Do the Right Thing
- Be Accountable
- Innovate Boldly
- Win Together
These values are lived every day — from leadership to frontline support — and help define what Uptime is known for in the legal tech space.
As Dennis puts it:
“We want to be known as the technology hub for modern law firms—the company firms trust to build, run, and scale their entire tech stack.”
Looking Forward: Innovation Without Limits
What excites the team most? The future.
With continued investment in AI, more acquisitions on the horizon, and growing adoption of LexWorkplace, Uptime is positioned to shape the next decade of legal tech.
For Dennis, every line of business holds opportunity — but LexWorkplace, in particular, feels like a game-changer. It’s not just a product; it’s a platform for innovation in legal work.
“We’re just getting started — and the sky’s the limit.”
Final Takeaway: Think Bigger
If Dennis could go back to day one, there’s one piece of advice he’d give himself.
Think bigger.
That mindset shift— from freelancer to founder, from product builder to industry leader — is what powered Uptime’s journey. And it’s what continues to shape the future of legal technology.
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