About the position

Brightwheel is the largest, fastest growing, and most loved platform in early ed, trusted by millions of educators and families every day. This role is for a Director, Training & Enablement who is an operator at their core, driving measurable outcomes with an AI-first mindset. The position involves building and scaling enablement as a system, onboarding and ongoing, tied to revenue, productivity, and retention outcomes. The ideal candidate thinks in systems, can diagnose performance gaps, operates with high agency and ownership, and is comfortable owning key metrics like ramp time, attainment, and productivity. This role requires strong cross-functional partnership and the ability to navigate ambiguity and seasonality. The opportunity is to build and evolve a business-critical function.

Responsibilities

• 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, 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
• Applied AI/automation to redesign enablement workflows and improve speed, consistency, or cost (builder strongly preferred)
• 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

Nice-to-haves

• High-velocity / SMB SaaS sales or post-sale (onboarding/CS) background
• RevOps or enablement-platform/admin depth (LMS, Gong/conversation intelligence, AI coaching tools)

Benefits

• We are a distributed team with remote employees across every US time zone, as well as select offices in the US and internationally.