Senior Director of Technology & Operations (AI-Native Transformation)

About the Opportunity

Early education is one of the most important determinants of childhood outcomes, a critical support for working families, and a $175B market that remains underserved by modern technology. The organization is the largest, fastest growing, and most loved platform in early ed, trusted by millions of educators and families every day. It is a three-time recipient of a prestigious industry award, backed by top investors.

Our Team

The team is passionate, talented, and customer-focused. They embody core leadership principles in their work and culture. The organization is a distributed team with remote employees across every US time zone, as well as select offices in the US and internationally.

Who You Are

This individual takes ownership beyond their remit and does not wait for a clean, fully-scoped mandate before moving. They lead through strong managers, but do not hide behind them: when something needs fixing, they are just as likely to jump in and fix it themselves as they are to coach someone else through it. They think critically and move fast, comfortable making calls with incomplete information and adjusting as they learn more.

This person will thrive in this role if they get energy from operating across multiple different functions, some they know deeply, some they are learning as they go, and they are honest with themselves and others about which is which. They will thrive here if they see an evolving scope as an opportunity rather than a liability.

What You'll Do

• Own the tech stack and teams that run operations at the organization.
• Lead established technical systems architecture and admin teams, redesigning the go-to-market stack for efficiency in an AI-first world.
• Personally own and drive select high-priority workstreams and initiatives directly, not solely through delegation.
• Deliver impactful, company-wide capabilities that improve business outcomes and drive key decisions, while supporting the business’s operating cadence.
• Manage a team of managers and individual contributors across functions, stepping in directly wherever the situation requires it.
• Drive AI-native transformation across every function owned, including hands-on build where appropriate.

What You've Done

• Led a multi-function technical or operational organization, managing managers across domains.
• Owned outcomes, not just outputs. Achieved business impact like growth, efficiency, conversion, retention, not just dashboards or insights. This role will help shape the future of the company.
• Worked closely enough with data engineering, software engineering, or technical systems to troubleshoot issues directly, not just interpret reports from others.
• Operated in a mid-size, high-growth company where building was required without inheriting mature infrastructure.

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• Navigated a role or organization structure that changed shape over time, and adapted their own scope and approach accordingly.
• Built AI-native workflows or tooling that materially changed how a team or company operated, not incremental automation, but real step-function change in how work got done.
• Collaborated closely with C-suite and executive leaders to shape strategy using data, including creating structure in ambiguity.

This role is not a fit if...

• You prefer a role with a fully-defined, static scope; this organization and mandate are still being shaped, and will continue to shift based on where strengths land.
• You lead primarily through delegation and expect managers to fully own execution; this role requires you to personally step in and drive work directly, not just direct others.
• You rely on authority to get things done; success in this role requires influencing across teams with competing priorities, not just managing within your organization.

The hiring organization is committed to creating a diverse and inclusive work environment and is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, genetics, disability, age, or veteran status.