Sr Director, Revenue Enablement

Role Overview

The Sr. Director, Revenue Enablement will own the enablement of the revenue organization to lead the transition of the company’s AI roadmap. This role requires someone who combines the rigor of a data-driven operator with the creativity of a learning designer and the credibility to influence senior GTM leaders.

What You Will Do

Design and operate a modern, AI-augmented enablement system, build scalable, role-based learning programs, establish a repeatable motion for enabling the field on AI product releases, define and own the success metrics that connect enablement activity to revenue outcomes, and build dashboards and reporting frameworks.

Why It Might Be a Fit

The right candidate thrives in a high-velocity, PE-backed environment where speed, measurability, and ROI are non-negotiable. You are here to build an enablement machine.

Requirements

• 12+ years of progressive experience in sales enablement, sales productivity, or GTM strategy within enterprise B2B SaaS
• Demonstrated track record of building scalable enablement programs that measurably improved ramp time, win rates, or pipeline conversion
• Deep fluency with AI-powered enablement tools and genuine conviction that AI fundamentally changes how sales organizations learn and execute
• Highly analytical: comfortable defining metrics, building dashboards, and using data to diagnose performance gaps and measure program impact
• Strong cross-functional credibility — able to partner with and influence senior leaders across Sales, Marketing, Product, and Customer Success
• Execution-oriented: equally comfortable setting strategy and rolling up sleeves to get programs built and running
• Outstanding communication and executive presence — able to translate complex GTM challenges into clear, compelling recommendations for senior audiences
• Bachelor’s degree required; MBA or advanced degree preferred

Benefits

• Employer subsidized medical/vision and dental coverage for full-time employees
• 401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay)
• Monthly stipend to support your work and productivity
• Flexible Time Away Program, plus Sick Time Off
• US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans
• US employees receive 12 paid holidays per year
• Up to 24 weeks of Parental Leave
• Personal paid Volunteer Day to support our community
• Opportunities for professional growth and development including access to Udemy online courses
• Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account
• Teleworking options from any registered location in the U.S. (role specific)