Brightwheel
Training & Enablement
Director,Training&Enablement
Neural analysis suggests this role is
optimal for Director candidates.
“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.
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
Applying for this Director, Training & Enablement role?
Most applicants get filtered before a human reads their resume. See if yours makes the cut.
How to Apply on Ashby
- Ashby is a fast modern ATS — most applications take under 3 minutes.
- The resume parser is strong; verify parsed experience dates and job titles.
- Custom screening questions are often scored algorithmically — answer completely.
- Location field affects geo-based screening; use your actual metro area.
ANONYMOUS · UNFILTERED
What do employees actually say about Brightwheel?
Real rants from real employees. Read before you apply.