Uptime Legal Company Culture

With a focus on strategic growth, product development, and innovation, Dennis Dimka has guided Uptime Legal to consistently rank among the Inc. 5000 fastest-growing companies and earn recognition as an Ernst & Young Entrepreneur of the Year Finalist. Dennis Dimka is the founder and CEO of Uptime Legal. Under Dennis’ leadership, Uptime Legal has grown organically and via acquisitions to become the #1 provider of cloud services to law firms, and has since expanded Uptime Legal’s portfolio to cloud-based legal software and digital marketing for law firms. Dennis manages the company’s strategic planning, marketing strategy, product development and manages the company’s Mergers & Acquisitions function. Dennis was named an Ernst & Young Entrepreneur of the Year Finalist, and Uptime Legal has ranked among the Inc. 5000 list of fastest-growing private companies in America for the past eight consecutive years. A Proven Leader in Legal Tech Dennis Dimka’s leadership has been a driving force behind Uptime Legal’s success and growth. With a background in both technology and business, he has consistently demonstrated his ability to navigate the rapidly changing landscape of the legal tech industry. Under his guidance, Uptime Legal has expanded its services from cloud solutions to comprehensive legal software and digital marketing, earning a reputation as the top provider of innovative solutions for law firms. As the founder and CEO, Dennis oversees all strategic initiatives, from product development to mergers and acquisitions, while ensuring that Uptime Legal stays ahead of industry trends. His ability to think long-term and execute on his vision has allowed the company to achieve consistent growth and industry recognition, including multiple listings on the Inc. 5000 and being named an Ernst & Young Entrepreneur of the Year finalist. Dennis’s leadership is characterized by a commitment to innovation and a passion for helping law firms thrive in a digital world. His deep understanding of both business and technology has positioned him as a visionary leader, inspiring the Uptime Legal team to continuously push the boundaries of what’s possible in legal tech.

Aaron Eittreim serves as the VP of Business Development of Uptime Legal Systems. Aaron started at Uptime Legal Systems in May of 2005. Aaron currently resides in Greater Minneapolis-St. Paul Area.

Erin Pickar serves as the Chief Operating Officer of Uptime Legal Systems. Erin started at Uptime Legal Systems in November of 2010. Erin currently resides in Greater Minneapolis-St. Paul Area.

Andrew Cabasso serves as the VP of Web Services of Uptime Legal Systems. Andrew currently resides in the Greater New York City Area.