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Director, Sales Enablement & Training

BrightwheelUnited StatesTraining & Enablement
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Salary
$213K - $235K USD
Job type
Full-time
Work mode
Remote
Posted
3 Jun 2026
Status
Open · checked 9d ago

About this role

Brightwheel seeks a strategic Director of Sales Enablement & Training to lead a unified training and operations organization across the United States. This remote role is tailored for an analytical and high-agency operator ready to redesign enablement systems using modern technology and artificial intelligence.

Role Overview

In this position, the Director owns the performance of a unified Training and Enablement organization consisting of approximately ten to twenty team members. Reporting directly into Operations, the leader oversees sales enablement, post-sales enablement, and enablement technology while driving measurable business outcomes. The individual shapes the future of professional growth by embedding artificial intelligence deeply into onboarding, coaching, and knowledge delivery workflows.

Key Responsibilities

Direct and execute an artificial intelligence-first enablement strategy that transforms how onboarding and continuous coaching operate.
Own end-to-end new hire onboarding systems alongside ongoing development initiatives for tenured representatives and managers.
Manage the entire enablement technology stack, including learning management systems, conversation intelligence platforms, and artificial intelligence coaching tools.
Track and report on critical business outcomes such as ramp time, attainment, productivity, quality assurance, and cost-to-train.
Collaborate across go-to-market, customer success, product, and finance departments to align strategies with broader corporate goals.
Lead, scale, and mentor a distributed team across multiple pillars while establishing high execution standards.

Requirements

Ten or more years of combined experience spanning go-to-market, operations, or enablement functions.
At least five years of specialized leadership experience managing enablement or training departments within high-growth organizations.
Minimum of five years managing teams, including supervising managers across sales and post-sale functions.
Proven track record of delivering quantified results, such as accelerated ramp times and improved quota attainment.
Demonstrated success in transforming organizational systems rather than merely maintaining existing training programs.
Hands-on experience applying artificial intelligence and automation to redesign enablement workflows.

Nice to Have

Background in high-velocity or small-to-medium business software-as-a-service sales and customer onboarding.
Revenue operations or enablement platform administrative depth with learning management systems and conversation intelligence software.

Skills and Tools

Artificial intelligence-driven enablement tools and workflows.
Learning Management Systems (LMS) administration.
Conversation intelligence and AI coaching or role-play software.
Data analytics for measuring business metrics like ramp time, attainment, and cost-to-train.
Cross-functional partnership and leadership across operations, finance, and product.

Salary and Benefits

Annual Salary: $213,000 to $235,000 USD.

About the Company

Brightwheel provides the leading platform for early education, supporting millions of families and educators every day across a substantial market. Recognized as a Cloud 100 company, the organization is backed by prominent investors including Mark Cuban, Bessemer, and Addition. The distributed team operates remotely across all United States time zones alongside select regional offices.

How to Apply

Interested candidates should visit the official Brightwheel careers page to submit their application. Ensure all communications originate from official company email addresses ending in @mybrightwheel.com.

Questions candidates ask

What is the salary range for the Director, Sales Enablement & Training role?

The annual salary for this position ranges from $213,000 to $235,000 USD.

Is this position remote?

Yes, this is a distributed remote role with employees located across every United States time zone.

How many years of experience are required for this job?

Candidates must have 10+ years of combined go-to-market, operations, or enablement experience, including at least 5 years leading enablement or training in high-growth companies and 5 years managing teams.

What department does this role report into?

This position reports directly into the Operations department.

What kind of mindset is Brightwheel looking for in this enablement leader?

Brightwheel requires a strong artificial intelligence-first mindset, looking for an operator who wants to fundamentally redesign enablement using AI rather than just generating content faster.

Ready to apply?

The application is on the official Brightwheel careers page.

Apply on company site