Director, Training & Enablement

Role Description

Brightwheel is seeking an operator at your core, who can drive measurable outcomes and prove it with numbers. You will bring a strong AI-first mindset and redesign how enablement works using AI. Your experience includes:

• Building and scaling enablement as a system, tied to revenue, productivity, and retention outcomes.
• Diagnosing performance gaps related to programs, tooling, talent, or measurement.
• Owning ramp time, attainment, productivity, quality/QA, and cost-to-train.
• Partnering cross-functionally across Sales, Customer Success, RevOps, Product, and Finance.
• Navigating ambiguity and making high-quality decisions quickly.
• Motivated to build and evolve a business-critical function.

What You'll Do

• Own the performance of a unified Training & Enablement organization (~10–20 people).
• Define and execute an AI-first enablement strategy.
• Own the end-to-end new-hire onboarding system and ongoing programs.
• Manage the enablement tech stack and measurement systems.
• Deliver against key outcomes including ramp time, attainment, productivity, and retention.
• Operate as a hands-on leader, diagnosing root causes and executing alongside the team.
• Partner cross-functionally to align enablement with company priorities.
• Build and lead a high-performing, distributed team.
• Identify opportunities to expand scope and impact over time.

Qualifications

• 10+ years of combined go-to-market, operations, and/or enablement experience.
• 5+ years leading enablement or training in high-growth organizations.
• 5+ years leading teams, including managing managers.
• A track record of quantified results you personally drove.
• Demonstrated ability to transform a function or system.
• Applied AI/automation to redesign enablement workflows.
• Built or improved enablement systems, tooling, and measurement.
• Deep comfort owning business-critical metrics and reporting to senior leadership.
• Successfully navigated ambiguous, fast-changing environments.
• Partnered cross-functionally to drive outcomes.

Requirements

• Nice to have: High-velocity / SMB SaaS sales or post-sale background.
• Nice to have: RevOps or enablement-platform/admin depth.

This role isn't a fit if:

• You're primarily a program manager or content owner focused on what you shipped rather than results.
• You prefer steady, defined scope over ambiguity and evolving mandates.
• You think of enablement as a content-and-training service rather than a system to redesign with AI.
• You optimize for polish over speed or prefer long planning cycles over rapid iteration.

Benefits

• Brightwheel is committed to creating a diverse and inclusive work environment.
• Equal opportunity employer.

Company Description

Brightwheel is the largest, fastest growing, and most loved platform in early education, trusted by millions of educators and families every day. We are backed by top investors including Addition, Bessemer, Emerson Collective, Lowercase Capital, Notable Capital, and Mark Cuban.