Product Support Engineer

About Playground

Playground is working to make excellent childcare accessible to all.

We’ve built best-in-class software that powers thousands of childcare providers across the country. We’ve raised millions in funding, secured statewide contracts, and are growing quickly. Our founders were recently recognized by Forbes 30 Under 30, and we’re just getting started.

Playground is a team of owners. We dive into hard problems. We move fast. We care deeply about craftsmanship and empathy both in our product and in how we serve customers.

Support at Playground is not a cost center. It is part of the product.

We’re hiring a Product Support Engineer to help us build support into a core product function.

This role sits at the intersection of customer empathy, product thinking, and systems design. You will deeply understand our product, solve complex customer problems, and build the systems that make support scalable, intelligent, and famously friendly.

You’ll work directly with customers and partner closely with Product and Engineering. You’ll own and improve our support tooling (Intercom + Fin), design automation workflows, surface product insights, and help shape how Playground evolves.

If you love:

• Going deep into a product and mastering its edge cases
• Debugging ambiguous issues and finding root causes
• Building automation that reduces repetitive work
• Turning support feedback into product improvements
• Designing systems that scale cleanly

This role is for you.

• Handle complex, high-impact customer issues end-to-end
• Develop deep expertise across billing, students, attendance, and operational workflows
• Diagnose product issues and determine when something is configuration, education, or a true bug
• Set a high bar for clarity, warmth, and confidence in communication
• Serve as an escalation point for nuanced cases

You are not a ticket router. You are a product expert.

• Design and maintain Intercom workflows (routing logic, SLAs, tags, escalation paths)
• Own Fin implementation: knowledge ingestion, guardrails, automation logic, and quality iteration
• Improve automation rates while maintaining trust and accuracy
• Identify repetitive patterns and build scalable automation solutions
• Debug automation breakdowns and continuously improve system performance

Support systems are product systems and you own their health.

• Translate recurring customer friction into clear product insights
• Partner with Engineering to triage bugs and prioritize fixes
• Surface product gaps backed by real customer context
• Participate in cross-functional conversations informed by live customer signals

You are a bridge between customers and product, not a middleman.

• Write and maintain high-quality Help Center content
• Ensure documentation aligns with product changes
• Design content that Fin can reliably reference
• Reduce ticket volume without reducing customer trust

Self-serve should feel empowering, not deflective.

• Define and track key support metrics (automation rate, SLA adherence, QA standards)
• Build QA processes that improve consistency and tone
• Create internal documentation that prevents knowledge silos
• Continuously refine workflows to reduce friction and prevent dropped balls

We believe that support quality compounds.

• 2–4 years experience in Product Support, Support Engineering, CX Ops, Biz Ops, or a systems-heavy SaaS role
• Hands‑on experience with Intercom or similar support tooling
• Strong systems thinking, technical background is a plus
• Comfortable jumping on video chats with customers
• High degree of ownership

• Direct experience with Fin or AI support agents
• Experience configuring automation tools (Zapier, Make, Workato)
• Comfort with light analytics (spreadsheets, dashboards, basic SQL)
• Experience building QA frameworks or support style guides

The annual salary range for this position is $110,000 - $130,000 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.

• Competitive salary + equity
• 3 weeks PTO
• Health, vision, and dental benefits
• $1200/year education stipend
• 401(k)
• Free lunch daily
• New Mac Book
• Fully in-office team in Denver
• High autonomy and real ownership

We’re building something meaningful. If that excites you, apply.