Customer & Marketplace Operations Leader

Wonderschool is transforming childcare by helping families find high-quality care and helping childcare providers start, operate, and grow successful businesses.

Our marketplace connects parents with childcare providers. Our software and services help providers reach families, manage their programs, and operate more effectively. We also work with employers that want to help their employees find childcare.

Wonderschool is a Series B company backed by Andreessen Horowitz (a16z), Goldman Sachs, and First Round Capital. We are cash flow positive and growing.

We believe childcare providers should be able to build sustainable businesses and that every family should be able to find care that meets their needs.

Customer operations at Wonderschool is about much more than answering questions. It is how we help families find care, help providers grow, retain customers, and create revenue.

We are looking for someone we can trust to own customer and marketplace operations across parents, childcare providers, and employers: how families find and enroll in care, how providers grow and stay on the platform, and how employers access childcare benefits for their teams. This person will lead support across phone, chat, email, and AI while building solutions that improve the customer experience and grow the business.

They do not need to have held this exact role before. We care more about their ability to learn quickly, exercise strong judgment, earn trust, take ownership, and build solutions.

This is a hands-on role. The person will answer calls, handle difficult situations, investigate problems, make financial and operational decisions, and build systems that allow the work to scale. They will have real authority over escalations, customer decisions, and how the team operates.

• Own support across phone, chat, email, and AI.
• Personally handle difficult calls and sophisticated customer situations.
• Establish high standards for response time, resolution, accuracy, tone, and follow-through.
• Make sure customers feel heard and their problems are actually resolved.
• Build a customer-obsessed team that takes complete ownership of outcomes.

• Learn how parents, providers, and employers use Wonderschool.
• Identify what is preventing customers from succeeding.
• Build practical solutions instead of repeatedly working around the same problems.
• Turn recurring failures into better tools, workflows, policies, training, and product experiences.
• Work with product and engineering to address underlying causes and verify that solutions work.

• Help more families successfully connect with childcare providers.
• Work with the parent and provider teams to identify and remove friction between searching for care and enrolling in it.
• Understand why families cannot find care and why providers cannot fill openings.
• Build operational solutions that improve outcomes for parents, providers, and employers.

• Treat customer operations as an important part of Wonderschool's growth.
• Identify opportunities to retain customers, increase adoption, and grow revenue.
• Recover customers at risk of leaving and identify expansion and cross-sell opportunities.
• Turn customer conversations into insights that improve the business.
• Learn the metrics and financial tradeoffs needed to make good decisions.

• Own the quality, tone, accuracy, and coverage of our AI support agent.
• Decide which situations AI should handle and when a person should take over.
• Audit conversations and build reliable escalation, handoff, and recovery systems.
• Use AI and automation to increase quality and capacity while preserving customer trust.

• Own the portfolio of services that help providers operate and grow: insurance, compliance, equipment, loans, payroll, photography, and more.
• Manage the vendor relationships and third-party partners that deliver most of these programs.
• Make careful financial, insurance, risk, and customer exception decisions.
• Build repeatable systems for complicated work.

• Hire, coach, and manage a lean, accountable team.
• Establish clear goals, ownership, service standards, and quality controls.
• Automate repeat work and make the team more effective.
• Surface important customer, revenue, retention, and operating trends to leadership.
• Move comfortably between strategy and detailed execution.

• More families successfully connect with childcare providers.
• Revenue and customer retention improve.
• Parents, providers, and employers receive fast, thoughtful support across every channel.
• Sophisticated situations are handled with sound judgment and complete ownership.
• The team builds solutions that eliminate recurring problems.
• AI resolves the right work, with seamless human handoffs.
• Provider programs operate reliably and help providers grow.
• The team consistently hits ambitious goals.

• Someone people can trust with important, ambiguous work.
• You take responsibility and follow through without constant direction.
• You have owned a customer-facing operation or program end to end and can point to a metric you were accountable for moving: retention, resolution, conversion, or revenue.
• You learn new customers, businesses, systems, and metrics quickly.
• You are willing to answer calls and work directly with customers.
• You stay calm and make good decisions in complicated situations.
• You build solutions, processes, and tools instead of simply identifying problems.
• You pull and interrogate your own numbers (spreadsheets at minimum, SQL a plus) rather than waiting for someone else's report.
• You care about revenue, retention, and business outcomes.
• You are comfortable making financial and operational decisions.
• You are excited to use AI and rethink customer operations.
• You can move between strategy, people management, and detailed execution.
• You are entrepreneurial, hungry, collaborative, and comfortable in a fast-moving environment.

We care more about evidence that you can do the work than your previous title or whether you have held this exact position before.

This role is based in our office in Rincon Hill, San Francisco, five to six days a week. That is by design: this is a hands-on role and the team is in the room.

We offer competitive market compensation, meaningful equity, and a full benefits package.

• Health benefits with up to 100% coverage for employee premiums and up to 80% for dependents
• Wifi and employee wellness stipends
• Flexible PTO, paid holidays, and mental wellness days
• Competitive parental leave (eligible after 6 months of employment)
• A highly collaborative, mission-driven workplace environment