
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
Join our April Webinar Series
Wed
1st
AI Workflows That Can Save You Hours of Admin Work a Week
Discover easy workflows to automate admin tasks and parent updates.
Wed
15th
The Tour + Follow-Up Script That Fills Classrooms
Get the script and follow-up steps to boost tour enrollments.
Tue
28th
The Staffing & Scheduling System That Prevents Director Burnout
Create schedules that support your team and reduce burnout.
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
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
Join Sasha Reiss, Co-Founder of Playground, for a free live webinar focused on practical enrollment strategies you can use right now to fill seats, manage waitlists, and plan ahead.
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
Whether you’re planning for summer camp or next year’s enrollment cycle, this webinar will give you clear, actionable steps to stay ahead.

Sasha Reiss
Co-Founder @ Playground
For Directors
Wednesday February 25th, 2026 | 4PM EST
The Future of Child Care: 2026 Trends to Watch
The child care landscape is evolving — and 2026 is set to bring meaningful shifts for early education providers.
Join Dr. Tamar Andrews, ECE professor and author, for a forward-looking conversation on the trends shaping the next chapter of child care. From policy developments and workforce changes to technology adoption and shifting family expectations, this session will help directors and operators understand what’s coming — and how to prepare.
Whether you’re planning for expansion, navigating staffing challenges, or simply trying to stay ahead of industry change, this session will provide insight to help you make informed decisions for the year ahead.

Dr. Tamar Andrews
ECE Professor & Author
For Directors
Friday February 13th, 2026 | 4:15PM EST
Optimize How Your Program Shows Up on Google
When families search for child care, Google decides which programs they see first and which ones they never see at all.
In this practical webinar, we’ll walk through how child care programs can improve their online visibility so more families can find them, recognize their program, and feel confident reaching out.
This session is designed for child care owners and directors who want clear, realistic guidance on improving their presence in search results without needing technical expertise or a marketing background.
In this webinar, you’ll learn:
How Google search results and AI-powered answers decide which child care programs to show
How to set up and optimize your Google presence so families can easily find and trust you
Simple website and content updates that can improve rankings and visibility
How small changes can lead to more tour requests and stronger enrollment over time
Whether you attend live or watch the recording later, you’ll walk away with practical tools and next steps you can apply right away.

Sasha Reiss
Co-Founder @ Playground
For Directors
Thursday, March 13 2025 | 2PM EST
Power to the Parents: Why You Need a Parent Advisory Committee
Imagine a child care center where parents aren’t just dropping off their children—they’re actively shaping the program and strengthening the community.
In this webinar, discover how a Parent Advisory Committee (PAC) can enhance family engagement, bridge communication gaps, and create a more collaborative environment between staff and guardians. Whether you’re a seasoned provider or just starting out, implementing a PAC is a powerful way to foster meaningful partnerships and gather valuable parent input
Join us to learn how to establish your own PAC, engage families effectively, and implement best practices for ongoing success.

Dr. Tamar Andrews
ECE Professor and Author
For Directors
Wednesday, February 26 2025 | 1PM EST
Automate, Engage, Grow: Marketing Strategies for Child Care Success
In today’s competitive child care landscape, guiding prospective families to your 'doorstep'—both literally and figuratively—takes more than just a couple of social media posts. Converting families from just interested to enrolled requires a strategic, technology-driven approach to marketing your child care program.
Join us as we explore top strategies to help you attract new families, nurture them with consistent communication, and enroll them—without adding more to your plate.
What you’ll learn:
The secrets to building a strong online presence that wins families over
How to automate every touchpoint to keep families engaged
How to nurture families from inquiry to enrollment without losing them
Ways to leverage technology to make marketing and enrollment effortless

Molly Farber
Product Manager, Playground
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