Founding GTM Engineer

ABOUT PLAYGROUND Playground is working to make excellent child care accessible to all. Playground has built best-in-class software that helps child care providers manage their entire business — billing, enrollment, communication, attendance, payroll, and more — all in one platform trusted by thousands of providers across the country. Playground is at an inflection point — and poised to grow extremely fast. We recently raised millions of dollars from top investors and are scaling our go-to-market engine to match. We are a team of owners, unafraid to dive into large, complex projects. If you're excited about solving real problems, moving fast, and building something that matters — keep reading. ABOUT THE ROLE Playground is hiring our First GTM Engineer to own the technical systems that power our revenue engine. You'll work directly with our team of 20+ sellers and partner with RevOps, Sales, and Marketing to build the automation, enrichment, and infrastructure that makes every activity more effective and help serve child care providers better. This isn't a "manage the CRM" or traditional admin role. You'll architect outbound workflows, build AI-driven enrichment pipelines, design lead routing logic, and automate the manual work that slows our GTM motion down. You'll write the logic that turns raw signals into pipeline and you'll measure what works. This role is AI-first, working directly with our founders and operations leaders to build systems for the future of sales. If you like building systems that directly drive revenue, this is for you. WHAT YOU'LL DO Build and scale the GTM engine - Design and deploy AI agents and automated workflows that power outbound prospecting, lead enrichment, and seller production across the full sales cycle - Build intelligent outbound sequences that use intent signals, account context, and AI-generated personalization to drive pipeline at scale - Orchestrate integrations across Salesforce, Gong, HubSpot, Chili Piper, our Enrichment Platform, n8n, and Intercom — connecting systems so data and actions work as one - Continuously evaluate and deploy new AI tooling and automation patterns to keep Playground's GTM motion at the forefront of internal operations ‘10x’ our sales organization - Identify manual, repetitive processes across the sales org and replace them with automated workflows - Work with team leaders to identify and execute on sales strategies and scale repeatable processes - Leverage Gong call data and CRM activity to surface insights, automate follow-ups, and improve coaching loops - Build and maintain integrations that keep data flowing cleanly between systems without rep intervention Improve inbound performance - Design and operationalize enrichment pipelines that score, route, and contextualize inbound leads before they hit a rep's queue - Build messaging frameworks and personalized automated nurture logic that improve conversion from lead to opportunity - Partner with Marketing to ensure lead handoff is clean and seamless Measure, learn, and ship fast - Build real-time dashboards and automated alerts that surface what's working across outbound, inbound, and seller activity — so the team can double down or pivot fast - Instrument every AI agent and automation with clear metrics: conversion lift, time saved, pipeline generated - Use data from Gong, Salesforce, and enrichment tools to identify new automation opportunities and feed insights back into the system YOU MIGHT WORK ON - Building an enrichment waterfall that auto-populates account intelligence before a sales-person touches a lead - Wiring Gong call outcomes into Salesforce to trigger automated next-step workflows - Designing lead routing logic in Chili Piper that dynamically assigns based on territory, segment, and capacity - Automating inbound/outbound personalization using AI prompts fed by account and contact enrichment data Building a dashboard that tracks enrichment coverage, outbound conversion, and rep efficiency in one