Head Of Shipping Jobs (NOW HIRING)

Wonderschool builds software and systems that help businesses operate, grow, and generate revenue. We started in childcare and are expanding into adjacent verticals including healthcare, microschools, and other service-based businesses. Our platform combines marketplace, SaaS, and government infrastructure.

We are a Series B company backed by Andreessen Horowitz, Goldman Sachs, Long Journey Ventures, and First Round Capital. The business is cash flow positive and expanding.

A core part of our strategy is using AI systems to increase speed and leverage across the company. We have a dedicated Head of AI Agent Systems role focused on building that capability. The Head of Engineering is responsible for building the high-performing engineering organization that can ship reliable, scalable products and fully leverage these systems.

The Head of Engineering owns product delivery, engineering execution, and team performance.

This role is responsible for ensuring the engineering team consistently ships high-quality, revenue-driving product quickly and reliably. It is a hands-on leadership role: you will manage the team, drive execution, improve development processes, and partner closely with Product and the Head of AI Agent Systems to increase velocity.

This role reports directly to the CEO.

• Ensure the team consistently ships high-quality product on time
• Reduce time from idea to production for core features
• Drive accountability for delivery across the team
• Prioritize and ship features tied to revenue quickly

• Manage, coach, and develop engineers
• Hire strong engineers and raise the bar over time
• Set a high performance standard and enforce it
• Address underperformance quickly and directly

• Improve engineering processes to increase speed without sacrificing quality
• Ensure code quality, testing, and reliability standards are maintained
• Partner with the Head of AI Agent Systems to integrate AI-driven workflows into the development process
• Ensure engineers adopt tools and systems that increase output

• Make and enforce key architectural decisions
• Ensure systems are scalable, maintainable, and aligned with product needs
• Drive simplification and reduce technical debt where it slows the business

• Work closely with the Head of Product to translate priorities into shipped product
• Ensure alignment between product requirements and engineering execution
• Support GTM and operations by delivering the systems needed to drive revenue

• Ensure engineering output directly supports revenue growth
• Improve the speed of shipping features that impact conversion, onboarding, and usage
• Balance speed and reliability to support long-term growth

• Engineering consistently ships high-quality product on time
• Time from idea to production is significantly reduced
• The team is high-performing with clear accountability
• Engineering output is clearly tied to revenue and product usage
• AI systems are fully integrated into engineering workflows

• Strong engineering background with experience building and shipping production systems
• Experience managing and scaling engineering teams
• Track record of delivering product quickly in a high-growth environment
• Strong technical judgment and ability to make architectural decisions
• Experience working closely with product and business teams

• Experience at a high-growth startup
• Experience improving engineering velocity and processes
• Experience integrating AI or automation into development workflows
• Background as a founder or early-stage engineer

• Someone who builds high-performing teams, not just systems
• Someone who drives execution and holds people accountable
• Someone who balances speed and quality effectively
• Someone who partners well with product and leadership
• Someone who is comfortable being hands-on when needed

Compensation is competitive and commensurate with experience. This role is eligible for equity.

Wonderschool offers a competitive benefits package, including:

• 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)

In-person, 5-6 days a week in our office in Rincon Hill, San Francisco.

Wonderschool is an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We plan and structure our interviews to directly assess skills and talent.