Sr Director, Revenue Enablement

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 consistent application of sales methodology and competitive positioning, translating enablement investment into measurable improvement in conversion and deal size
• Enablement 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 next

What You Will Bring

Required

• 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

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