Director of Sales Enablement & Training, Brightwheel
$213-257k
OTE
Offers equity and commission
Online platform for early education management
Be an early applicant
Online platform for early education management
501-1000 employees
Be an early applicant
$213-257k
OTE
Offers equity and commission
501-1000 employees
Company mission
To improve education for young children, given the vital importance of early education for later life.
Role
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
- 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)
What the job involves
- 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
Our take
Childcare and teaching is a profession fraught with pressures and paperwork and yet it remains relatively ill attended to by advances in tech and software. Brightwheel want to revolutionize this, focusing on facilitating the administrative and communicative relationship between schools, carers and parents or guardians.
As tech enters the classrooms there are various apps focusing on the education itself with fewer actually handling the communications for schools. Brightwheel's platform helps increase parental and teacher engagement with students everyday, while helping small education businesses save money, time, and to grow.
Brightwheel is carving out a name for itself as a service valuable for its exciting and useful new updates. It was quick to adapt to school closures too by offering distance learning capabilities and health testing. And on top of this, it also caters to childcare in lower-income areas with a freemium model. Making its a go-to platform for early education.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-15% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Feb 2021
$55m
SERIES C
Oct 2018
$21m
SERIES B
Total funding: $88.8m
Company HQ
Financial District, San Francisco, CA
Leadership
Dave Vasen
(Founder & CEO)Dave began their career at Morgan Stanley, before spending a year at Cisco and 3 years as a Bain Consultant. They then worked at Amazon for 2 years, and after taking on several Advisory roles they founded Brightwheel in 2014, serving as the CEO since.
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