Director, Training & Enablement

brightwheel

Director of Training & Enablement at Brightwheel leading AI-first strategies and team performance for education technology sector.

Posted 6/4/2026full-timeRemote • 🇺🇸 United StatesLead💰 $213,000 - $257,000 per yearWebsite

About the role

Key responsibilities & impact

Own the performance of a unified Training & Enablement organization (~10–20 people) spanning Sales Enablement, Post-Sales Enablement, and Enablement Tech/Systems, reporting into Operations
Define and execute an AI-first enablement strategy
Own the end-to-end new-hire onboarding system
Own the enablement tech stack and the measurement systems
Deliver against key outcomes including ramp time, new-hire and ongoing attainment
Operate as a hands-on leader
Partner cross-functionally to ensure enablement is aligned
Build and lead a high-performing, distributed team
Identify opportunities to expand scope and impact over time

Requirements

What you’ll need

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

Benefits

Comp & perks

Comprehensive medical, dental, and vision coverage
Generous paid parental leave
Flexible PTO so you can recharge when you need it
Local retirement or savings plans (e.g., 401(k) in the U.S.)

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI-first enablement strategynew-hire onboarding systemenablement tech stackmeasurement systemsenablement systemsautomationworkflowsbusiness-critical metricsreportingquantified results

Soft Skills

hands-on leadercross-functional collaborationteam buildingleadershipnavigating ambiguityinfluencing decisionsoperational excellencestrategic thinkingperformance managementadaptability