Sr Director, Revenue Enablement

About the role

The Sr. Director, Revenue Enablement is accountable for delivering measurable impact on commercial performance — not just managing programs. The expectation is that this role produces outcomes that are visible to the CMO, CRO, and the board.

Responsibilities

• Enablement Velocity & AI-Driven Sales Motion
• Design and operate a modern, AI-augmented enablement system that dramatically compresses time-to-productivity for new hires and time-to-adoption for new product capabilities.
• Build scalable, role-based learning programs that leverage AI tools — including adaptive learning platforms, AI-assisted coaching, and automated content delivery — to increase throughput without proportional headcount growth.
• Establish a repeatable motion for enabling the field on AI product releases: from launch readiness to certified competency, with measurable adoption milestones.
• Revenue Impact, Metrics & Strategy
• Define and own the success metrics that connect enablement activity to revenue outcomes — ramp time, win rates, pipeline conversion, expansion rates, and forecast accuracy.
• Build dashboards and reporting frameworks that make the ROI of enablement visible to the CMO and CRO, and that inform program decisions.
• Translate Smartsheet’s broader GTM strategy into quarterly enablement priorities with clear owners, milestones, and accountability.
• Field Readiness & Product Marketing Partnership
• Partner closely with Product Marketing to ensure that AI feature messaging is translated into crisp, field-ready narratives, objection handling frameworks, and competitive positioning.
• Own the motion that takes a product release from “launched” to “seller-certified” — designing the programs, content, and inspection cadences that make readiness a standard, not an exception.
• Coaching, Methodology & Execution Discipline
• Operationalize Strategic Value Selling methodology, supported by structured playbooks, AI-assisted call review tools, and inspection cadences.
• Define and continuously evolve the enterprise B2B selling competencies required to win in Smartsheet’s market — including AI fluency as a core selling skill.
• Drive consistent execution of sales methodology, deal rigor, and pipeline hygiene through both programming and data-driven inspection.
• Content, Tools & Technology
• Own the enablement content ecosystem: messaging frameworks, playbooks, competitive battlecards, training assets, and partner materials.
• Lead the evaluation, adoption, and optimization of AI-powered enablement tools — from conversational intelligence platforms to AI content generation and readiness scoring.
• Partner with Revenue Operations to ensure the enablement and sales technology stack is integrated, instrumented, and driving measurable seller productivity.
• Team Leadership
• Build, inspire, and scale a high-performing Enablement organization, fostering a culture of accountability, continuous growth, and measurable impact.
• Own and steward the Enablement budget, making strategic investment decisions that directly accelerate revenue growth and sales productivity.
• Shape company-wide strategic direction as a senior leadership stakeholder, driving program decisions with a focus on operational excellence and measurable business outcomes.
• Define and champion the policies, processes, and best practices that elevate Smartsheet's sales and marketing organization, influencing how the business operates at scale.

Qualifications

• 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)

Pay

• US Base Salary Pay Range: $187,500 - $247,500 USD

Schedule

• Role specific teleworking options from any registered location in the U.S.

Equal Opportunity Employer

Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, India, and Singapore. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.