Deep Dive: Launching and Selling Payroll with OnTheClock

OnTheClock helps small businesses simplify time tracking so they can focus on growing their teams. But as those businesses expanded, managing their workforce became more complex — and payroll quickly emerged as the missing piece. To meet that need, OnTheClock partnered with Check to embed payroll directly into their platform.

To hear how the launch came together, Dylan from Check sat down with Jeff Hughes, Customer Success Director at OnTheClock. In this conversation, Jeff shares why payroll was critical for customer retention and growth, how Check helped the team go to market faster, and what’s fueling their early success.

Dylan: If you don’t mind introducing yourself as well—because I know you.

Jeff: I’m Jeff Hughes, Customer Success Director here at OnTheClock. I’ve been with the company almost two years.  I’ve spent most of my career in customer success organizations selling SaaS across cybersecurity, workforce management, and customer experience analytics.

Dylan: What do you love most about OnTheClock?

Jeff: There’s a couple things, Dylan. First and foremost, we’re a small but scrappy and mighty team here at OnTheClock, and we really focus on helping small businesses become successful. If I think about the biggest cost to a small business, it’s their team and their workforce. We make it really easy for them to modernize their time tracking.

Then, it's how do we help small businesses stay successful? Because keeping them as a customer means keeping them in business. I really enjoy that mission. And the team here is amazing—super collaborative, really focused on helping our customers and providing the best experience for small business owners.

Dylan: What triggered you to look at bringing payroll internal? And why did you select Check?

Jeff: One of the things we know is, as you grow, managing your workforce becomes more complicated. Tracking time is what you start with, but then you need workers’ comp, benefits, all of that. As our customers' businesses grew, it became easier for them to move to their payroll provider and use their time tracking—because we didn’t have a payroll solution to offer them. So, for retention and growth, payroll was essential to add into our product suite. Then, we started looking for partners with the expertise to help us build it, implement it, and sell it.

I wasn’t involved in the vendor evaluation—I came in after selection—but what stood out was Check's reputation. We had a robust list of requirements and functionality. It came down to having a trusted partner who would be with us throughout the process—a company that has the industry expertise, something we could embed in the product, and a team to help us be successful in the go-to-market strategy. Check stood out there. Plus, some of the other names out there could be viewed as competitors and it would be difficult to get into business and partnership with a competitor.

Dylan: How is selling payroll different from your other OnTheClock products and from your broader career?

Jeff: It’s really complicated and really important, right? I came from cybersecurity: you don’t want to get hacked. Same idea: your team needs to get paid. It’s probably the largest line item in your P&L. It has to be accurate and timely. Payroll is the lifeblood of any business.

For OnTheClock, this was our first new product for existing customers, so it was an exploration. How do we identify, segment, and upsell our base to a new offering with a new pricing structure—something not part of their initial engagement? We had to figure that out.

Dylan: We did a few in-person sales trainings during onboarding. Was it helpful?

Jeff: We’re not payroll experts, so partnering with someone who has the history, breadth of knowledge, and expertise was critical so we could learn from our partner.

The way we've grown, our business has been very organic. It's word of mouth. Somebody who might have used us at a previous company that goes somewhere else and brings OnTheClock in because it's easy to use, it's easy to set up. You track your time for your workforce.

When you start talking about selling payroll on top of that, you have to convince a customer of your reputation. The ease of that migration, the cost transparency. There's a whole lot of decisions and variables that come into play when you're making a decision to switch. Having you and the Go-to-Market team helping guide our activities and give us feedback and encouragement has been really critical to our growth in selling payroll.

If you wanted to know what has resonated the most with us, it was the feedback to our sales team. How to hone their craft, how to approach cold calling, how to handle demos, and how to close a sale was really important. Also, the webinars on how to get exposure to our base and prospects, capitalize on leads, and follow up were big for our sales.

Dylan: What more could we have done to shorten rep ramp or get more top-of-funnel faster? And if you were telling “Jeff in Jan 2025,” what would you say?

Jeff: I think we spent a disproportionate amount of time on technical implementation and not as much on go-to-market, so we scrambled at the end. Before you first came onsite, we were scratching our heads on how to make the most productive use of the time.

We didn’t truly have someone owning go-to-market. I stepped in because it aligned with selling to our base, but it required me, Chad  from marketing, Noah from support, and later Crystal (implementation). There were lots of cooks. It would have helped if we were told, “You need an owner. Here’s how they should come to weekly/monthly touch bases and report what’s happening.”

But when you came onsite more recently, one of the things that I was really proud of is that when you went through the list of the go-to-market things that we should be doing, and we were hitting most of them.

Dylan: Could you speak to the change you’ve seen in the reps? How they started, what we did to polish techniques, and where they’re at now?

Jeff: Their trajectory started with a lot of enthusiasm and no success. Over the last few months, we’ve learned to have meaningful conversations, show benefits, and enroll. In the last 60 days, it’s morphed to confidence in the product, proper discovery, position to the use case, and then close, or at least, set the exact next step.

We brought on Jamie, a seasoned sales leader. He’s continuing the coaching. Demos and leads are coming in frequently now. Selling is repetition. More at-bats equals more hits. And they’ve really improved their swing.

Dylan: Any specific ways Check helped in that journey?

Jeff: You did individual coaching with each rep—which was really helpful to highlight opportunity areas for each. Collectively, you pushed focus on the demo script and what to walk through in a payroll demonstration. Then, pushing us to measure the right metrics thatput our performance in context, and showed us where to improve.

Initial coaching and guidance, setting the stage, and then helping us understand whether we were actually succeeding in those metrics.

Dylan: What's the biggest lesson or insight at each stage of the sales cycle?

Jeff: Top of funnel is where we’ve had the most success. Awareness, the multiple ways we brought attention to payroll, generated a lot of leads. With webinars, the lesson was “just do them.” We worried about appearing polished or professional, but the feedback was that our authenticity matched our culture and resonated.

Then mid funnel, the demo evolved the most. It’s less about the exact clicks and more about confidence that we understand your needs, and we’ll handle them. More discovery, reassurance, less “show you every step.”

And bottom of funnel, it’s getting the business out of the demos. Right decision-makers involved, clear next step, when they’ll enroll. That’s where we’re focusing now.

Dylan: Would you recommend the embedded experience with Check to other platforms?

Jeff: From ease of execution perspective, taking an already industry-proven enrollment process and embedding it into our product was the easiest and quickest way to get to market. The flow makes sense. Once you’re interested in payroll, you start with eligibility and enrollment, then migrate seamlessly through Check’s setup components. If we had to build each component individually, it would have taken a lot longer. With Check, we launched last December, versus potentially still talking about it today.