Director, Sales Enablement & Training

About the role

Brightwheel is the largest, fastest-growing, and most-loved platform in early education, trusted by millions of educators and families. This role is part of Operations, responsible for the performance of a unified Training & Enablement organization spanning Sales Enablement, Post-Sales Enablement, and Enablement Tech/Systems.

Responsibilities

• Own the performance of a unified Training & Enablement organization (~10–20 people)
• Define and execute an AI-first enablement strategy, embedding AI deeply into onboarding, ongoing coaching, certification, conversation intelligence, and knowledge delivery
• Own the end-to-end new-hire onboarding system and the ongoing programs that uplevel tenured reps and managers
• Own the enablement tech stack (LMS, conversation intelligence, AI coaching/role play, knowledge tools) and the measurement systems that prove enablement impact
• Deliver against key outcomes including ramp time, new-hire and ongoing attainment, productivity, quality/QA, cost-to-train, and contribution to retention
• Operate as a hands-on leader — diagnosing root causes, setting direction, and executing alongside the team
• Partner cross-functionally to ensure enablement is aligned with go-to-market, post-sale, product, and finance priorities
• Build and lead a high-performing, distributed team across all three pillars, setting a high bar for execution and continuous improvement
• Identify opportunities to expand scope and impact over time, contributing to broader operational leadership

Requirements

10+ years of combined go-to-market, operations, and/or enablement experience, including 5+ years leading enablement or training, in high-growth organizations

5+ years leading teams, including managing managers — ideally across more than one function (sales and post-sale)

A track record of quantified results you personally drove (conversion improved, ramp time reduced, attainment improved, productivity or cost gains)

Demonstrated ability to transform a function or system, not just maintain existing programs

Built or improved enablement systems, tooling, and measurement that scaled with business growth

Deep comfort owning business-critical metrics and reporting credibly to senior leadership

Successfully navigated ambiguous, fast-changing, and seasonal environments, bringing structure and results

Partnered cross-functionally to drive outcomes and influence company-level decisions

Qualifications

Nice to have: High-velocity / SMB SaaS sales or post-sale (onboarding/CS) background

Nice to have: RevOps or enablement-platform/admin depth (LMS, Gong/conversation intelligence, AI coaching tools)