Sr Director, Revenue Enablement

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day.About Smartsheet Smartsheet is a leading enterprise platform for dynamic work, empowering organizations to plan, execute, and report on work at scale. Backed by multiple private equity firms, Smartsheet operates with the rigor, discipline, and growth orientation of a world-class PE-backed SaaS company. We are at a pivotal moment — accelerating our AI capabilities, evolving our operating model, and building the organizational infrastructure to scale intelligently. The Opportunity Smartsheet is in the midst of a significant transformation. The company’s AI roadmap is fundamentally changing what our platform can do — and the pace of that innovation is accelerating. The opportunity in front of us is clear. The challenge is execution: how do we ensure that our revenue organization can lead the transition? As Sr. Director, Revenue Enablement, you will own that answer. This role is built around the need to deliver learning and enablement that keeps pace with our roadmap, and aligns every member of the GTM to key principles in value selling, customer value and AI solutions expertise. You will design and operate the systems, programs, and tools that make that happen. This role reports directly to the CMO and sits at the intersection of sales productivity, AI adoption, and commercial execution. It 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. 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. What You Will Own 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. Other duties as assigned.  How You Will Drive Business Value 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: Faster time-to-productivity: Reduce ramp time for new AEs and CSMs through structured onboarding and role-based learning programs that are AI-assisted and continuously optimized Accelerated AI feature adoption: Shrink the lag between AI product releases and field readiness — ensuring sellers can demo, position, and sell new capabilities within weeks of launch, not quarters Higher win rates and deal quality: Drive consist