Scaling Up Business with Bill Gallagher

People First, And Then Profits Follow with Dean Mathews

14 snips
Oct 1, 2025
Dean Mathews, founder of OnTheClock, shares his journey of building a bootstrapped time-tracking SaaS that supports over 200,000 users monthly. He emphasizes creating a people-first culture, viewing his team as the backbone of success. Dean discusses how rapid learning and adaptation fueled growth, the myth of work-life balance, and the importance of trust in delegation. He highlights the shift towards a sales motion while maintaining a family-like work environment, underscoring his commitment to what truly matters in business.
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ANECDOTE

Kitchen-Table Start Turned Real Product

  • Dean discovered the market need on accounting forums and built OnTheClock in a few months.
  • That scrappy start grew into a product used by ~16,000 customers and ~200,000 people monthly.
ANECDOTE

Early Users Shaped The Product

  • Early customers like a hair replacement shop became beta users and guided development.
  • Dean personally reached out to every early signup and iterated the product from customer feedback.
INSIGHT

People-First Company As A Strategic Choice

  • Dean built a people-first company because he hated the divide between front and back office roles.
  • He now considers building and leveling up his team his primary CEO job.
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