Remote Director, Training & Enablement

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

, 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

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 dont 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, youre comfortable owning ramp time, attainment, productivity, quality/QA, and cost-to-train, and youre 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 youre not limited by traditional definitions of enablement. Youre motivated by the opportunity to build and evolve a business-critical function.

What Youll 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 isnt a fit if:
Youre 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. Youre 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. Youve used AI tools for personal productivity, but havent 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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