Webinars

Learn from the pros who built it.

Live sessions and on-demand replays covering everything from getting started to scaling your service business with WorkBoss.

Coming Up

Upcoming live sessions

Apr 17
Live Thursday, April 17 · 2:00 PM ET

Getting Started with WorkBoss: From Sign-Up to First Invoice

A step-by-step walkthrough covering account setup, adding your first customer, creating an estimate, and sending your first invoice — all in under 45 minutes.

Register Free
May 8
Live Thursday, May 8 · 2:00 PM ET

Scheduling & Dispatch: Keep Your Crew Moving

Learn how to manage your calendar, assign jobs to technicians, handle last-minute changes, and keep everyone in the loop — without a single phone call.

Register Free
May 22
Live Thursday, May 22 · 2:00 PM ET

Estimates That Win: Pricing, Presentations & Follow-Ups

Our most popular session. Learn how top-performing shops use WorkBoss estimates to close more jobs, upsell options, and automate follow-up reminders.

Register Free

Why attend

More than a product demo.

Real-World Workflows

Every session is taught by someone who’s actually run a service business. We show you the exact workflows our best customers use — not theory.

Live Q&A

Ask questions and get answers in real time from our product team. Bring your specific use case — we’ll walk through it together.

45 Minutes, Tops

We respect your time. Sessions are focused, actionable, and recorded so you can watch again later or catch what you missed.

On-demand

Watch anytime, on your schedule.

Missed a live session? Every webinar is recorded and available to watch on demand. No sign-up required.

Replay · 42 min

Invoicing & Payments: Get Paid in Days, Not Weeks

How to set up payment processing, send automatic reminders, and give your customers the option to pay instantly from their phone.

March 2026
Replay · 38 min

CRM Deep Dive: Organize Your Customers Like a Pro

Tags, custom fields, service history, and pipeline views — everything you need to stop losing track of leads and repeat customers.

February 2026
Replay · 44 min

From Pen & Paper to WorkBoss: A Migration Story

A live walkthrough with a real customer who switched from paper-based systems. Learn what to import, what to skip, and how to get your team onboard fast.

January 2026
Professional trade tools arranged on a workbench
“I joined one webinar to learn about invoicing. By the end, I’d completely changed how I run estimates too. These sessions actually save you time.”

— Jake M., Plumbing Contractor, Nashville TN

Don’t just learn about it — try it.

Start your 14-day free trial and follow along with any of our webinars. No credit card required.

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