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 view

Who You Are

• You have 3-6+ years of experience in GTM Engineering, Revenue Operations, Sales Operations, Growth Ops, or a technical GTM role
• You've built workflows and automations end-to-end
• You're comfortable working with APIs, webhooks, CRM architecture, and data integrations. Bonus if you've written Python or JavaScript to solve GTM problems
• You understand the sales funnel deeply - not just the data model, but why stages exist and what moves deals forward
• You're a systems thinker who designs durable, production-ready solutions
• You're scrappy, proactive, and unafraid to get into the weeds. You don't wait for permission to fix broken processes
• You communicate clearly with both sellers and leadership - you can explain what you built and why it matters
• Bonus: You've worked with Salesforce, Gong, Clay (or similar), HubSpot, or n8n. Experience with AI-driven enrichment or outbound automation is a big plus

Compensation:

• The annual salary range for this position is $160,000 - $210,000, subject to standard withholding and applicable taxes
• Job level and actual compensation will be decided on factors including, but not limited to, individual qualifications objectively assessed during the interview process (including skills and prior relevant experience, potential impact, and scope of role), market demands, and specific work location. The listed range is a guideline, and the range for this role may be modified.

What Makes a Great Fit

If you're a hustler who's excited to join a mission-driven, early-stage company with ownership, craft, and empathy at its core - we want to hear from you. The Playground team is fully in-office in Union Square, NYC. Please make sure you are open to a fully in-person role before applying.

Why Join Playground

• Competitive salary + equity
• 3 weeks of PTO
• Health, vision, and dental benefits
• $1200/year education stipend
• 401(k)
• Free lunch daily
• New MacBook and any equipment you need
• Collaborative and supportive work culture with a high level of autonomy and room for growth
• Help accelerate our mission to make excellent child care accessible to all!

How to Apply: If you're a hustler who's excited to join a mission-driven, early-stage company with ownership, craftsmanship, and empathy at the center of what we do, apply now. The Playground Team is fully in-office in Union Square, NYC. Please make sure you are open to a fully in-person role before applying.

Check out: https://www.tryplayground.com/about to learn more about our journey and co-founders Dan, Josh, and Sasha.