
Free live events, trainings, and expert sessions, from wherever you are. Let's learn, grow and build together.

The Work Smarter Webinar Series
with
Sasha Reiss
Co-Founder @ Playground
For Directors
Wednesday, May 20th | 5PM EDT
Live 30-Minute Walkthrough of Playground
If you’re exploring new child care management software, this is the fastest, easiest way to see what Playground can actually do for your program.
Join Ryan, one of Playground’s Senior Account Executives, for a live walkthrough of the platform where he’ll show you how centers use Playground to simplify billing, enrollment, communication, attendance, and day-to-day operations
Attend live and you’ll automatically be entered to win $50 toward your classroom essentials.

For Directors
Tuesday, May 19 2026 | 3PM EDT
Meet Playground: The Story Behind Child Care's Purpose-Built Software
Playground was built for child care from day one. In this webinar, our founder walks through why Playground exists, who it's built for, and how it actually runs the operational side of a program: billing, enrollment, family communication, compliance, staff management, and reporting.
You'll leave with:
The story behind Playground
A look at how directors use it day to day, from enrollment through payroll
A live Q&A for you to get your questions answered and discover Playground for your program

For Directors
Friday, May 8 2026 | 1PM EDT
Getting Ready for Summer Camp 2026: Billing, Safety, and Everything in Between
We are giving away 2 $50 gift cards to live webinar attendees. Want bonus entries? Click here
Summer camp changes everything overnight. New schedules, new rosters, new billing structures, new families, new safety considerations. This session walks through how to set up camp the right way from the start, so June isn't spent putting out fires.
You'll leave with:
A summer safety checklist you can actually use (water play, field trips, sunscreen policies, heat protocols)
Operational tips for staffing ratios, late pickups, and camp-specific attendance workflows
Fun camp activity ideas to set your summer up for success

For Directors
Tuesday, April 28th 2026 | 3pm EST
The Staffing & Scheduling System That Prevents Director Burnout
Staffing is often the biggest source of stress for directors, but it doesn't have to be. We want to help you move from constantly putting out fires to running a smooth, predictable operation.
In this session, we will share a proven framework that helps you:
Create flexible schedules that keep your team happy and reduce turnover.
Handle last-minute call-outs without panic.
Set clear boundaries that protect your time and prevent burnout.

Sasha Reiss
Co-Founder @ Playground
For Directors
Monday, April 20th 2026 | 4PM EDT
5 Money Mistakes Child Care Owners Make
Most child care directors are running full programs and still feel uncertain about their finances.
Not because business is bad. Because the data they're looking at isn't giving them the full picture. Payout reports that miss fees and discounts. Billing software that doesn't connect to the bookkeeping. Financials reviewed once a year, at tax time, when it's too late to act on what they find.
This webinar is built for child care directors and program owners who want financial clarity without hiring a full-time accountant or rebuilding their systems from scratch.
Alexis from Little Ledgers walks through 5 of the most common financial mistakes child care directors make, with practical, specific fixes for each one. Every fix is designed to work with systems you likely already use, including Playground.
Email: alexis@littleledgers.com
CPA Firm: Little Ledgers

Alexis Louis
CPA, Founder of Little Ledgers
For Directors
Wednesday, April 15th 2026 | 3pm EST
The Tour + Follow-Up Script That Fills Classrooms
Most childcare centers don’t struggle with marketing. They struggle with conversion.
Tours feel inconsistent
Follow-up gets delayed
Families say “we’ll think about it”
And classrooms stay partially empty.
In this tactical session, we’ll break down the exact tour structure and follow-up system high-performing centers use to turn interest into enrollment. You'll walk away with:
A tour script that highlights your center's unique strengths.
A follow-up system that keeps families engaged after they leave.
Proven strategies to increase your conversion rates and fill empty spots.

Sasha Reiss
Co-Founder @ Playground
For Directors
Wednesday, April 1st 2026 | 4:15PM
AI Workflows That Can Save You Hours of Admin Work a Week
Childcare directors and operators are overwhelmed — not because they lack commitment, but because their workflows are manual, fragmented, and reactive.
In this session, we’ll break down where AI fits inside a childcare center in practical, operational terms.
You’ll leave with:
A clear understanding of which workflows should be automated
A framework for reclaiming 5–10+ hours per week
A roadmap for using AI to improve enrollment, communication, and reporting — without sacrificing quality

Sasha Reiss
Co-Founder @ Playground
For Directors
Friday, January 30, 2026 | 4:15PM EST
Enrollment Strategies for Peak Season
In this session, you’ll learn:
How to fill empty seats during peak enrollment months
Best practices for managing and communicating with waitlists
How to prepare your enrollment process for summer and the year ahead

Sasha Reiss
Co-Founder @ Playground
Load More








