
Dean Mathews, OnTheClock
From Side Project to $5M+ ARR as a Self-Funded SaaS
Dean Mathews is the founder and CEO of OnTheClock, a time tracking software that helps small businesses manage their employees' hours. In 2004, Dean was sitting at his kitchen table with his laptop, browsing through small business and accounting forums. He noticed a pattern: people were constantly complaining about not being able to find a reliable, easy-to-use time tracking system for their companies. Dean, who was working as a software consultant at the time, had a lightbulb moment. He thought, "I can build that for them." He spent the next few months building the first version of OnTheClock and launched it in June 2004 while still maintaining his consulting work. For the next decade, OnTheClock remained Dean's passion project. He dedicated about 20 hours a week to it, squeezing in time between client projects to improve the product and learn about marketing. He never talked directly to prospective customers to validate the idea - instead he relied on forum research, competitor analysis, and simple logic: small businesses with hourly employees have to track time. Despite the limited attention, the self-funded SaaS grew steadily through SEO and word-of-mouth referrals. By 2015, OnTheClock had hit a major milestone - $1 million in annual recurring revenue. The following year, Dean took the plunge. He handed off his consulting clients and brought his brother Mark on board to develop a mobile app. Focusing full-time on the business accelerated growth, but it also brought new challenges. Dean had to shift from being a hands-on developer to leading a team - something he was initially reluctant to do after seeing toxic management dynamics at consulting clients. Along the way, Dean faced other hurdles. Paid advertising failed repeatedly - even with an outside agency and significant budget, clicks never translated to signups. He had to learn how to be an effective leader and build a culture he could be proud of. Today, OnTheClock serves about 18,000 customers. The company generates well beyond $5M in annual recurring revenue as a fully self-funded SaaS with a team of 22 people and zero outside funding.






















