Brightwheel

Training & Enablement

Director,Training&Enablement

$213–257k United States FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Director candidates.

The Brief

“Director, Training & Enablement at Brightwheel. Skills: Training and Enablement, AI-first enablement, Enablement systems, Team leadership. Own performance of Training & Enablement organization. Define AI-first enablement strategy”

What You'll Achieve.

Drive measurable outcomes; Improve ramp time; Improve attainment; Improve productivity; Improve retention; Reduce cost-to-train

Industry & Context.

Training & Enablement
Problems you'll solve

Diagnose performance gaps; Root cause analysis

What They're Looking For.

Must Have

10+ years go-to-market experience, 10+ years operations experience, 10+ years enablement experience, 5+ years leading enablement, 5+ years leading training, 5+ years leading teams, 5+ years managing managers

Nice to Have

High-velocity SaaS sales background, SMB SaaS sales background, High-velocity post-sale background, SMB post-sale background, RevOps depth, Enablement-platform admin depth, LMS admin depth, Gong admin depth, AI coaching tools admin depth

What You'll Do.

Own performance of Training & Enablement organization

Define AI-first enablement strategy

Embed AI into onboarding

Embed AI into ongoing coaching

Embed AI into certification

Embed AI into conversation intelligence

Embed AI into knowledge delivery

Own new-hire onboarding system

Own enablement tech stack

Own measurement systems

Deliver against ramp time

Deliver against attainment

Deliver against productivity

Deliver against quality/QA

Deliver against cost-to-train

Deliver against contribution to retention

Operate as hands-on leader

Partner cross-functionally

Ensure enablement alignment

Build high-performing team

Lead high-performing team

Set high bar for execution

Set high bar for continuous improvement

Identify opportunities to expand scope

Contribute to operational leadership

How You'll Work.

Team & Collaboration

Cross-functional partner; Sales partnership; Customer Success partnership; RevOps partnership; Product partnership; Finance partnership; Go-to-market alignment; Post-sale alignment; Distributed team leadership

Full Job Description

Our Mission and Opportunity Early education is one of the most important determinants of childhood outcomes, a critical support for working families, and a $175B market that remains underserved by modern technology. Brightwheel is the largest, fastest growing, and most loved platform in early ed, trusted by millions of educators and families every day. We are a three-time Cloud 100 company https://www.forbes.com/lists/cloud100/a, backed by top investors including Addition, Bessemer, Emerson Collective, Lowercase Capital, Notable Capital, and Mark Cuban. Our Team Our team is passionate, talented, and customer-focused. We embody our Leadership Principles https://mybrightwheel.com/about/ in our work and culture. We are a distributed team with remote employees across every US time zone, as well as select offices in the US and internationally. 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 func

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