Customer Operations Automation Lead

About Playground
Playground is working to make excellent child care accessible to all. Playground has built best in class software to manage all aspects of running a child care business. Playground has raised millions of dollars in funding, has several Statewide contracts, and is working with thousands of schools across the country. Our founders were recently recognized by Forbes as 30 under 30, and our work has been recognized across the country.
Playground is at an inflection point, growing at a quick pace. Playground is compromised of a team of owners who are not afraid to dive into large, complex projects.
About the Role

We’re hiring a Customer Operations Automation Lead to help us build a customer support experience that becomes part of our identity: famously friendly, deeply helpful, and scaled through high-quality AI automation.

We see support becoming a product function, and in this role you are becoming a product leader. This role sits at the intersection of support craft + operational rigor + AI enablement. We see support becoming a product function, and in this role you are becoming a product leader. You’ll design and implement the workflows, playbooks, and automation systems that allow customers to get fast answers while still feeling like they’re being supported by real humans who care.

You’ll work directly with our Support team as a player/coach. You will answer tickets, develop expertise and opinions, then partner with Product and Engineering to build a world-class support experience powered by Intercom + Fin.

If you love:

• making support feel warm, confident, and high-trust

• building systems and processes that scale cleanly

• using AI to reduce repetitive work (without sacrificing quality)

• designing workflows that make customers feel taken care of
  …this is the role.

What You'll Own:

• Design and document the support experience: tone, voice, macro style, service principles, and escalation standards

• Build and maintain high-quality response templates, macros, and playbooks that feel human and consistent

• Improve customer experience across channels, ensuring every interaction is clear, kind, and effective

• Partner with Support leadership to make support feel like Playground rather than generic.

• Configure and optimize workflows in Intercom: routing, assignment rules, ticket taxonomy, tags, SLAs, and escalation paths

• Own and continuously improve our Fin implementation: knowledge sources, automation logic, guardrails, and response quality

• Build processes for AI-assisted support and ensure our automation stays accurate, helpful, and on-brand

• Identify repetitive patterns and implement automation to handle them at scale

• Develop continuous feedback and evaluation loops so Fin improves month over month

• Build and maintain a high-quality help center that Fin can reliably reference

• Create support content that reduces ticket volume while maintaining a great experience

• Ensure content is discoverable, correct, and aligned with product changes

• Establish an ongoing cadence for documentation improvements based on ticket trends

• Build and refine workflows that reduce support friction and prevent issues from falling through the cracks

• Implement QA checks, response standards, and internal documentation that improve consistency

• Track key support metrics and translate insights into clear process improvements

• Own cross-functional feedback loops with Product and Engineering (bugs, product gaps, repeated issues)

What You Need:

• Have 2–3 years of experience in BizOps, CX Ops, Support Ops, Consulting, or an operational role at a tech/SaaS startup

• Have hands-on experience with Intercom (or similar tools) and enjoy building workflows and automation

• Care deeply about tone, clarity, and human-centered support

• Are excited about AI support automation and comfortable iterating systems to improve quality

• Can own projects end-to-end: diagnose problems, design solutions, implement changes, and measure results

• Are highly organized and detail-oriented — support systems depend on it

• Communicate well and enjoy cross-functional collaboration

• Direct experience with Fin or other AI support agents

• Experience building workflows with Zapier/Make/Workato or internal tooling

• Experience designing support QA programs or style guides

• Comfortable with light analytics (spreadsheets, dashboards, SQL)

Support is not an afterthought here, it’s a product. You’ll help build a support experience that customers remember and want to tell their friends about. You’ll also get to work on one of the most modern parts of customer support: using AI (Fin) to scale support while making it feel even more human.

This role is ideal for someone who wants to shape the future of support — not just operate within it.

Compensation

• The annual salary range for this position is $70,000 - $120,000 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.

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

• Collaborative and supportive work culture with a high level of autonomy and room for growth

• Help accelerate our mission to make excellent childcare 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 Denver, CO. 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.