Sr Director, Revenue Enablement (Boston)

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 SmartsheetSmartsheet 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 OpportunitySmartsheet 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 OwnEnablement 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 & TechnologyOwn 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 LeadershipBuild, 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 ValueThe 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 optimizedAccelerated 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 quartersHigher win rates and deal quality: Drive consistent application of sales methodology and competitive positioning, translating enablement investment into measurable improvement in conversion and deal sizeEnablement ROI visibility: Build the reporting infrastructure that connects program activity to commercial outcomes, providing the CMO and CRO with clear, data-driven insight into what is working and what to invest in nextWhat You Will BringRequired12+ years of progressive experience in sales enablement, sales productivity, or GTM strategy within enterprise B2B SaaSDemonstrated track record of building scalable enablement programs that measurably improved ramp time, win rates, or pipeline conversionDeep fluency with AI-powered enablement tools and genuine conviction that AI fundamentally changes how sales organizations learn and executeHighly analytical: comfortable defining metrics, building dashboards, and using data to diagnose performance gaps and measure program impactStrong cross-functional credibility — able to partner with and influence senior leaders across Sales, Marketing, Product, and Customer SuccessExecution-oriented: equally comfortable setting strategy and rolling up sleeves to get programs built and runningOutstanding communication and executive presence — able to translate complex GTM challenges into clear, compelling recommendations for senior audiencesBachelor’s degree required; MBA or advanced degree preferredPreferredExperience in a PE-backed or sponsor-backed environment, with familiarity operating at the pace, rigor, and accountability PE ownership demandsBackground in AI enablement or future-of-work strategy, particularly in organizations actively deploying AI/ML into core products or go-to-market motionsPrior experience at SaaS or enterprise software companies that have undergone significant product or GTM transitionsFamiliarity with enterprise sales methodologies (Value Selling, Challenger, or equivalent) and how to operationalize them at scaleCurrent US Perks & Benefits:Employer subsidized medical/vision and dental coverage for full-time employees401k 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 productivityFlexible Time Away Program, plus Sick Time OffUS employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plansUS employees receive 12 paid holidays per yearUp to 24 weeks of Parental LeavePersonal paid Volunteer Day to support our communityOpportunities for professional growth and development including access to Udemy online coursesCompany Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet accountTeleworking options from any registered location in the U.S. (role specific)Smartsheet provides a competitive base salary range for roles that may be hired in different geographic areas we are licensed to operate our business from. Actual compensation is determined by several factors including, but not limited to, level of professional, educational experience, skills, and specific candidate location. In addition, this role will be eligible for a market competitive incentive opportunity.US Base Salary Pay Range$187,500—$247,500 USDGet to Know Us:At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You’ll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you’re doing work that stretches you, excites you, and connects you to something bigger, that’s magic at work. Let’s build what’s next, together.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 i