Building Employee Retention Through Systems With Dean Matthews

Dean Matthews

Dean Matthews is the Founder and CEO of OnTheClock, an employee scheduling, time tracking, payroll, and HR platform serving more than 16,000 businesses across the United States. A software developer and entrepreneur at heart, Dean built OnTheClock with a focus on simplicity, transparency, and customer experience. His people-first leadership philosophy has helped him scale both a successful technology company and a strong internal culture built around trust and alignment.

Here’s a glimpse of what you’ll learn:

[03:10] How Dean identified the need for a simple, reliable online time tracking solution.
[06:10] Why intuitive systems and excellent customer support create long-term success.
[07:30] The biggest mistakes businesses make when managing employee time tracking.
[09:00] Why employee turnover creates major operational and knowledge-transfer challenges.
[13:20] How values-based hiring helped Dean build a strong company culture

In this episode:

Processes are only as strong as the people executing them—and Dean Matthews believes great systems should make life easier for both employers and employees.

In this episode, Adi Klevit interviews Dean Matthews, Founder and CEO of OnTheClock, about the relationship between systems, employee experience, and company culture. Dean shares how he started OnTheClock over two decades ago after noticing that business owners were struggling to find a simple, reliable way to track employee time and schedules.

Adi and Dean explore one of the biggest challenges entrepreneurs face: managing people effectively while maintaining operational consistency. Dean explains how many businesses still rely on manual systems, spreadsheets, or verbal communication, which often leads to errors, confusion, and employee frustration. By implementing transparent systems, businesses can improve accuracy, accountability, and trust across the organization.

The conversation also highlights the importance of culture and retention. Dean shares how intentionally building a people-first workplace helped him scale beyond being a solo entrepreneur into leading a growing team. Through values-based hiring, clear processes, and strong leadership, he has created an environment where employees feel supported and empowered to succeed.

Perhaps the biggest takeaway is that systems do more than improve efficiency—they create stability, clarity, and a better overall employee experience.

Resources mentioned in this episode:

Quotable Moments:

“People are the ones actually executing the processes.”
“No instructions required—that was our design philosophy.”
“Transparency creates happier employees.”
“Tribal knowledge walks out the door when employees leave.”
“Culture starts with values alignment.

Action Steps:

Evaluate whether your current systems create transparency and clarity for employees.
Replace manual tracking methods with standardized digital systems where possible.
Document tribal knowledge before key employees leave the organization.
Build onboarding and training systems that help employees succeed faster.
Hire team members who align with your company values and culture

Sponsor for this episode:

This episode is brought to you by Business Success Consulting Group.

At Business Success Consulting Group, we create custom processes and tailor-made management systems so businesses can thrive.

Businesses simply can’t survive without workable systems and well-documented processes. That’s why our team of experienced professionals takes care of it for you.

We provide business owners, entrepreneurs, and key executives with six phases to success, along with the long-lasting systems necessary to support business expansion.

So, what are you waiting for? Do yourself a favor and cut the chaos out of your business.

Visit bizsuccesscg.com today or email info@bizsuccesscg.com to schedule a free consultation.