Senior Director, Revenue Enablement

This is a fully remote position, open to applicants in United States.

📋 Description

• Design and manage a cutting-edge, AI-enhanced enablement system that significantly reduces the time it takes for new hires to reach productivity and for new product capabilities to be adopted.

• Develop scalable, role-specific learning programs that utilize AI tools — such as adaptive learning platforms, AI-assisted coaching, and automated content delivery — to boost throughput without a corresponding increase in headcount.

• Create a consistent process for enabling the field on AI product launches: from readiness for launch to certified proficiency, with quantifiable adoption milestones.

• Define and take ownership of the success metrics that link enablement activities to revenue results — including ramp time, win rates, pipeline conversion, expansion rates, and forecast accuracy.

• Develop dashboards and reporting systems that clearly demonstrate the ROI of enablement to the CMO and CRO, guiding program-related decisions.

• Translate Smartsheet’s broader go-to-market strategy into quarterly enablement priorities with designated owners, milestones, and accountability.

• Collaborate closely with Product Marketing to ensure that AI feature messaging is converted into clear, field-ready narratives, objection handling frameworks, and competitive positioning.

• Manage the process that transitions a product release from “launched” to “seller-certified” — creating the programs, content, and inspection schedules that make readiness the norm, not the exception.

• Operationalize the Strategic Value Selling methodology, supported by structured playbooks, AI-assisted call review tools, and regular inspection schedules.

• Define and continuously refine the enterprise B2B selling competencies needed to succeed in Smartsheet’s market — with AI fluency as a fundamental selling skill.

• Ensure consistent execution of sales methodology, deal rigor, and pipeline hygiene through both programming initiatives and data-driven inspections.

• Oversee the enablement content ecosystem: messaging frameworks, playbooks, competitive battlecards, training materials, and partner resources.

• Lead the assessment, adoption, and enhancement of AI-driven enablement tools — including conversational intelligence platforms and AI content generation and readiness scoring.

• Work closely with Revenue Operations to ensure that the enablement and sales technology stack is well-integrated, instrumented, and driving measurable productivity for sellers.

• Build, motivate, and expand a high-performing Enablement organization, nurturing a culture of accountability, continuous improvement, and measurable impact.

• Manage and oversee the Enablement budget, making strategic investment choices that directly facilitate revenue growth and sales productivity.

• Influence company-wide strategic direction as a senior leadership stakeholder, guiding program decisions with a focus on operational excellence and measurable business outcomes.

⛳️ Requirements

• A minimum of 12 years of progressive experience in sales enablement, sales productivity, or go-to-market strategy within the enterprise B2B SaaS sector.

• Proven track record of developing scalable enablement programs that have measurably enhanced ramp time, win rates, or pipeline conversion.

• Deep understanding of AI-powered enablement tools and a firm belief that AI fundamentally transforms how sales organizations learn and operate.

• Highly analytical: adept at defining metrics, creating dashboards, and utilizing data to identify performance gaps and evaluate program effectiveness.

• Strong cross-functional credibility — capable of collaborating with and influencing senior leaders across Sales, Marketing, Product, and Customer Success.

• Execution-focused: equally comfortable with strategic planning and hands-on implementation to get programs developed and operational.

• Exceptional communication skills and executive presence — able to distill complex go-to-market challenges into clear, persuasive recommendations for senior audiences.

• Bachelor’s degree required; an MBA or advanced degree is preferred.

🏝️ Benefits

• Employer-subsidized medical, vision, and dental coverage for full-time employees.

• 401k Match to assist you in saving for your future (50% of your contribution up to the first 6% of your eligible pay).

• Monthly stipend to support your work and enhance productivity.

• Flexible Time Away Program, along with Sick Time Off.

• U.S. employees are automatically enrolled in Smartsheet-sponsored life insurance, short-term, and long-term disability plans.

• U.S. employees receive 12 paid holidays each year.

• Up to 24 weeks of Parental Leave.

• Personal paid Volunteer Day to contribute to our community.

• Opportunities for professional growth and development, including access to Udemy online courses.

• Company-funded perks, which include a counseling membership, local retail discounts, and your own personal Smartsheet account.

• Teleworking options available from any registered location in the U.S. (role-specific).