Calendely / Calendar Best Practices
Automate demo scheduling to increase show rates and strengthen payroll sales conversations.
Using a Calendar Booking Tool to Improve Demo Quality & Show Rates
A simple, well-configured calendar booking tool—like Calendly, SavvyCal, or Chili Piper—can dramatically increase the volume, quality, and reliability of your payroll demo pipeline. By capturing key context before the meeting and following a disciplined reminder cadence, your team will hold more demos, have deeper conversations, and convert more employers into payroll customers.
This guide outlines how the Check GTM team should set up and use a calendar booking tool to accelerate your payroll go-to-market motion.
Why Calendar Booking Tools Matter for Payroll Sales
A great booking experience supports your GTM motion by:
- Reducing friction for employers to schedule a payroll demo.
- Gathering key qualification details upfront, so you enter demos prepared and confident.
- Boosting show-up rates with automated reminders.
- Creating consistency across sales reps and partners.
- Reinforcing your value proposition, especially around time savings, cost savings, and better support for employers switching to your payroll platform.
Done well, your booking workflow becomes a quiet but powerful engine driving more closed-won deals.
How to Set Up Your Calendar Booking Flow
1. Create a “Payroll Demo” Event Type
Use your booking tool to create a dedicated event specifically for payroll demos (20–30 minutes).
Key settings to enable:
- Buffer times between meetings
- Time zone detection
- Automatic confirmation email
- Limits on daily bookings so reps stay effective
2. Add Required Questions to Capture Employer Context
These questions ensure every demo begins with meaningful insight into the employer’s current situation. Add them as required fields in your calendar booking form:
- “Which payroll provider are you currently using?”
- “How many employees do you currently pay?”
- “What is prompting you to explore a new payroll platform?”
- “Are there any specific topics or challenges you want to discuss during the demo?”
- “Is there anything we should review in advance (e.g., pay schedules, contractor needs, benefits)?”
These inputs help the sales team tailor each conversation and connect Check’s payroll value—especially time and cost savings—to the employer’s real pain points.
3. Add Optional Questions to Warm the Sales Conversation
Consider including optional prompts like:
- “What’s most important to you when evaluating payroll platforms?”
- “Have you recently experienced issues with payroll accuracy or support?”
- “Do you prefer a fast overview demo or a detailed walkthrough?”
These create natural openings for your reps during the call.
4. Include Clear Messaging About Time & Money Savings
Your event description should reinforce your core value proposition. Example:
During this demo, we’ll show how our payroll platform can save you hours each month, reduce manual admin work, and lower your total payroll costs compared to your current provider.
This frames expectations and strengthens the motivation to attend.
Recommended 3-Touch Reminder Cadence
A consistent reminder sequence is critical to improving show rates, especially in payroll where employers are busy and interruptions are constant.
Enable the following automated reminders:
1. Calendar Invite (Immediately after booking)
Include:
- Meeting link
- Agenda
- What they will learn (time savings, cost savings, better support)
- What to prepare (e.g., current provider and pay schedule)
2. 24-Hour Reminder
Reinforce:
- What to expect
- How the platform helps them save time and money
- A quick “reschedule link” to avoid no-shows
3. 2-Hour Reminder
Short, direct:
- Meeting link
- Bullet list of top benefits
- Encouragement to bring any payroll challenges they want to solve
4. 10-Minute Reminder
Simple and actionable:
- Direct join link
- “We’re looking forward to helping you save time and payroll costs.”
This cadence significantly increases attendance and builds momentum toward the call.
Best Practices for the Sales Team
- Review booking details before every demo. Come prepared with a POV on how you will save them time and money.
- Tailor your intro to their provider. A customer coming from ADP expects something different than a customer on Gusto.
- Reference the issues they listed. This builds trust and shortens the discovery process.
- Send follow-up materials. Include a recap of time and cost savings, next steps, and a shared link to reschedule or book additional meetings.
Summary
A well-implemented calendar booking flow is a high-ROI GTM asset. By capturing key employer context early, reinforcing your value proposition, and following a structured reminder cadence, your sales team will run better demos, reduce no-shows, and consistently convert more employers into payroll customers.
Last updated on December 16, 2025