Responsibilities
- Lead the performance of a unified Training & Enablement team of approximately 10 to 20 people, covering Sales Enablement, Post-Sales Enablement, and Enablement Tech/Systems, reporting into Operations.
- Develop and implement an AI-first enablement strategy, integrating AI deeply into onboarding, ongoing coaching, certification, conversation intelligence, and knowledge delivery.
- Manage the complete new-hire onboarding system and ongoing programs that enhance the skills of tenured representatives and managers.
- Oversee the enablement technology stack, including LMS, conversation intelligence, AI coaching and role play, and knowledge tools, along with measurement systems to demonstrate enablement impact.
- Achieve key outcomes such as reduced ramp time, improved new-hire and ongoing attainment, increased productivity, enhanced quality and QA, lower cost-to-train, and contributions to retention.
- Act as a hands-on leader by diagnosing root causes, setting direction, and executing tasks alongside the team.
- Collaborate across functions to align enablement with go-to-market, post-sale, product, and finance priorities.
- Build and lead a high-performing, distributed team across all three pillars, setting high standards for execution and continuous improvement.
- Identify opportunities to expand scope and impact over time, contributing to broader operational leadership.
Requirements
- At least 10 years of combined go-to-market, operations, or enablement experience, including 5 or more years leading enablement or training in high-growth organizations.
- At least 5 years of team leadership experience, including managing managers, ideally across sales and post-sale functions.
- A proven record of quantified results personally driven, such as improved conversion, reduced ramp time, improved attainment, or productivity or cost gains.
- Demonstrated ability to transform a function or system, not just maintain existing programs.
- Applied AI or automation to redesign enablement workflows and improve speed, consistency, or cost; builder experience 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
- Background in high-velocity or SMB SaaS sales or post-sale functions such as onboarding or customer success.
- Depth in RevOps or enablement platform administration, including LMS, Gong or conversation intelligence, and AI coaching tools.
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 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.
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.
Other
- 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.
- Protecting Our Applicants: Please be aware of recruiting scams impersonating Brightwheel. All legitimate communications come from @mybrightwheel.com addresses, and we never ask for payment or sensitive personal data as part of our hiring process. If you suspect fraudulent contact, reach out to security@mybrightwheel.com.
