Sr Director, Revenue Enablement

Smartsheet • Bellevue, WA

1d • Remote

About The Position

Smartsheet is seeking a Sr. Director, Revenue Enablement to lead the company's transformation by ensuring the revenue organization can effectively transition to new AI capabilities. This role will design and operate learning and enablement programs that keep pace with the company's AI roadmap, focusing on value selling, customer value, and AI solutions expertise. Reporting directly to the CMO, this position is crucial for sales productivity, AI adoption, and commercial execution in a high-velocity, PE-backed environment. The ideal candidate will combine operational rigor with creative learning design and strong influencing skills to build a robust 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 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.

Nice To Haves

• MBA or advanced degree preferred.
• 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.

Responsibilities

• Design and operate a modern, AI-augmented enablement system to improve time-to-productivity for new hires and time-to-adoption for new product capabilities.
• Build scalable, role-based learning programs leveraging AI tools for increased throughput.
• Establish a repeatable process for enabling the field on AI product releases, from launch readiness to certified competency.
• Define and own success metrics connecting enablement activity to revenue outcomes (ramp time, win rates, pipeline conversion, expansion rates, forecast accuracy).
• Build dashboards and reporting frameworks to demonstrate the ROI of enablement.
• Translate Smartsheet’s GTM strategy into quarterly enablement priorities with clear owners and accountability.
• Partner with Product Marketing to translate AI feature messaging into field-ready narratives and objection handling frameworks.
• Own the process of taking a product release from launch to seller certification.
• Operationalize Strategic Value Selling methodology with playbooks and AI-assisted tools.
• Define and evolve enterprise B2B selling competencies, including AI fluency.
• Drive consistent execution of sales methodology, deal rigor, and pipeline hygiene.
• Own the enablement content ecosystem, including messaging frameworks, playbooks, and training assets.
• Lead the evaluation, adoption, and optimization of AI-powered enablement tools.
• Partner with Revenue Operations to ensure the enablement and sales technology stack is integrated and driving seller productivity.
• Build, inspire, and scale a high-performing Enablement organization.
• Own and manage the Enablement budget, making strategic investment decisions.
• Shape company-wide strategic direction as a senior leadership stakeholder.
• Define and champion policies, processes, and best practices for the sales and marketing organization.
• Other duties as assigned.

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)

What This Job Offers

• Job Type: Full-time
• Career Level: Director