Director, Sales Enablement & Training

Who You Are

You are an operator at your core, you don't just design programs, you drive measurable outcomes and can prove it with numbers. You bring a strong AI-first mindset and are excited to fundamentally redesign how enablement works using AI, not just generate content faster. You have a track record of building and scaling enablement as a system, onboarding and ongoing, tied to revenue, productivity, and retention outcomes, and you think in systems, able to diagnose whether a performance gap is a program, tooling, talent, or measurement problem.

You operate with high agency and ownership, proactively identifying opportunities and driving change without waiting for direction. Analytically, you're comfortable owning ramp time, attainment, productivity, quality/QA, and cost-to-train, and you're a strong cross-functional partner across Sales, Customer Success, RevOps, Product, and Finance. You navigate ambiguity and seasonality well, making high-quality, high judgement decisions quickly, and you're not limited by traditional definitions of enablement. You're motivated by the opportunity to build and evolve a business-critical function.

What You'll Do

• 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

What You Bring

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

This role isn't a fit if

• You're primarily a program manager or content owner who measures success by what you shipped rather than what results moved
• You prefer steady, defined scope and stable environments over ambiguity, evolving mandates, and seasonal surges. You're looking to run a well-defined, well-oiled enablement function rather than rebuild and redesign one from first principles
• You think of enablement as a content-and-training service to optimize incrementally, rather than a system to fundamentally redesign with AI. You've used AI tools for personal productivity, but haven't applied AI to redesign workflows or deliver step-function improvements
• You optimize for polish over speed, or prefer long planning cycles over rapid iteration

Brightwheel is committed to creating a diverse and inclusive work environment and is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

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