Director, Sales Enablement & Training

Brightwheel is the largest, fastest growing, and most loved platform in early education, trusted by millions of educators and families every day. It is a three-time Cloud 100 company, backed by top investors including Addition, Bessemer, Emerson Collective, Lowercase Capital, Notable Capital, and Mark Cuban. The team is distributed with remote employees across every US time zone, as well as select offices in the US and internationally.

As Director, Sales Enablement & Training, you will 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. You will define and execute an AI-first enablement strategy, embedding AI deeply into onboarding, ongoing coaching, certification, conversation intelligence, and knowledge delivery. You will own the end-to-end new-hire onboarding system and ongoing programs that uplevel tenured reps and managers, as well as the enablement tech stack (LMS, conversation intelligence, AI coaching/role play, knowledge tools) and the measurement systems that prove enablement impact. You will deliver against key outcomes including ramp time, new-hire and ongoing attainment, productivity, quality/QA, cost-to-train, and contribution to retention. You will operate as a hands-on leader, partner cross-functionally to align enablement with go-to-market, post-sale, product, and finance priorities, and build and lead a high-performing, distributed team across all three pillars.

You are an operator at your core, driving measurable outcomes and proving them with numbers. You bring a strong AI-first mindset and are excited to fundamentally redesign how enablement works using AI. You have a track record of building and scaling enablement as a system, tied to revenue, productivity, and retention outcomes. You think in systems, diagnose performance gaps, and operate with high agency and ownership. You are analytically comfortable owning ramp time, attainment, productivity, quality/QA, and cost-to-train, and you are a strong cross-functional partner across Sales, Customer Success, RevOps, Product, and Finance.

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

On Target Earnings $213K – $235K, offers equity.

Apply via the provided application link.