Senior Director of Revenue Enablement

Join Smartsheet, a company undergoing a significant transformation driven by AI innovation. As the Senior Director of Revenue Enablement, you will design and operate systems, programs, and tools that align the go-to-market (GTM) team with key principles in value selling, customer value, and AI solutions expertise. You will report directly to the CMO and play a crucial role in driving commercial execution and sales productivity.

• Design and operate a modern, AI-augmented enablement system that compresses time-to-productivity for new hires and time-to-adoption for new product capabilities.
• Define and own the success metrics that connect enablement activity to revenue outcomes, and build dashboards and reporting frameworks that make the ROI of enablement visible to the CMO and CRO.
• Partner closely with Product Marketing to ensure that AI feature messaging is translated into crisp, field-ready narratives, objection handling frameworks, and competitive positioning.
• 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
• Bachelor’s degree required; MBA or advanced degree preferred
• Demonstrated track record of building scalable enablement programs that measurably improved ramp time, win rates, or pipeline conversion
• 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
• Deep fluency with AI-powered enablement tools and genuine conviction that AI fundamentally changes how sales organizations learn and execute
• 12+ years of progressive experience in sales enablement, sales productivity, or GTM strategy within enterprise B2B SaaS
• Experience in a PE-backed or sponsor-backed environment, with familiarity operating at the pace, rigor, and accountability PE ownership demands
• Background in AI enablement or future-of-work strategy, particularly in organizations actively deploying AI/ML into core products or go-to-market motions
• Prior experience at SaaS or enterprise software companies that have undergone significant product or GTM transitions
• Familiarity with enterprise sales methodologies (Value Selling, Challenger, or equivalent) and how to operationalize them at scale