Sr Director, Revenue Enablement

Smartsheet•Bellevue, WA

1d•$187,500 - $247,500•Remote

About The Position

Smartsheet is in the midst of a significant transformation, with an accelerating AI roadmap fundamentally changing the platform. The Sr. Director, Revenue Enablement will own the answer to how the revenue organization can lead this transition. This role is responsible for delivering learning and enablement that keeps pace with the roadmap and aligns the GTM team to key principles in value selling, customer value, and AI solutions expertise. The individual will design and operate the systems, programs, and tools to achieve this. This role reports directly to the CMO and sits at the intersection of sales productivity, AI adoption, and commercial execution. It requires a blend of data-driven operational rigor, learning design creativity, and the ability to influence senior GTM leaders. The ideal candidate thrives in a high-velocity, PE-backed environment where speed, measurability, and ROI are critical.

Requirements

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.

Nice To Haves

MBA or advanced degree 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.

Responsibilities

Design and operate a modern, AI-augmented enablement system to compress time-to-productivity for new hires and time-to-adoption for new product capabilities.
Build scalable, role-based learning programs leveraging AI tools (adaptive learning, AI-assisted coaching, automated content delivery) to increase throughput without proportional headcount growth.
Establish a repeatable motion for enabling the field on AI product releases, covering launch readiness to certified competency with measurable adoption milestones.
Define and own success metrics connecting enablement activity to revenue outcomes (ramp time, win rates, pipeline conversion, expansion rates, forecast accuracy).
Build dashboards and reporting frameworks to make enablement ROI visible to the CMO and CRO, informing program decisions.
Translate Smartsheet’s broader GTM strategy into quarterly enablement priorities with clear owners, milestones, and accountability.
Partner closely with Product Marketing to translate AI feature messaging into field-ready narratives, objection handling frameworks, and competitive positioning.
Own the motion for product releases from 'launched' to 'seller-certified,' designing programs, content, and inspection cadences for readiness.
Operationalize Strategic Value Selling methodology with structured playbooks, AI-assisted call review tools, and inspection cadences.
Define and evolve enterprise B2B selling competencies, including AI fluency as a core selling skill.
Drive consistent execution of sales methodology, deal rigor, and pipeline hygiene through programming and data-driven inspection.
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 (conversational intelligence, AI content generation, readiness scoring).
Partner with Revenue Operations to ensure the enablement and sales technology stack is integrated, instrumented, and driving measurable seller productivity.
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 to 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 policies, processes, and best practices that elevate Smartsheet's sales and marketing organization.
Perform other duties as assigned.

Benefits

Employer subsidized medical/vision and dental coverage for full-time employees
401k 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 productivity
Flexible Time Away Program, plus Sick Time Off
Company-sponsored life insurance, short-term, and long-term disability plans
12 paid holidays per year
Up to 24 weeks of Parental Leave
Personal paid Volunteer Day to support our community
Opportunities for professional growth and development including access to Udemy online courses
Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account
Teleworking options from any registered location in the U.S. (role specific)