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.

Smartsheet is a leading enterprise platform for dynamic work, empowering organizations to plan, execute, and report on work ked 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.

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.

• 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.
• 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.

• 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.

• 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.

• Own the enablement content ecosystem: messaging frameworks, playbooks, competitive battle cards, training…