Director, Sales Enablement & Training

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.

- 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

- 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)

- 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