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 u
Benefits
Remote work options
Additional Information
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.
Brightwheel · US