Sr Director, Revenue Enablement

4 hours, 1 minute ago
Full-time
Executive
Sales and Business Development
Smartsheet

Smartsheet

Smartsheet provides an enterprise work management platform that enables teams to efficiently manage projects, automate processes, and enhance collaboration through a user-friendly interface that combines spreadsheet functionality with advanced workflow...

Internet Software & Services
1K-5K
Founded 2005

Description

  • Design and operate an AI-augmented enablement system that reduces time-to-productivity for new hires and accelerates adoption of new product capabilities.
  • Build scalable, role-based learning programs using AI tools such as adaptive learning platforms, AI-assisted coaching, and automated content delivery.
  • Establish a repeatable field-enablement motion for AI product releases, from launch readiness through certified competency and adoption milestones.
  • Define and own enablement success metrics tied to revenue outcomes, including ramp time, win rates, pipeline conversion, expansion rates, and forecast accuracy.
  • Build dashboards and reporting frameworks that make enablement ROI visible to senior revenue leadership and guide program decisions.
  • Translate GTM strategy into quarterly enablement priorities with clear owners, milestones, and accountability.
  • Partner with Product Marketing to turn AI feature messaging into field-ready narratives, objection handling, and competitive positioning.
  • Operationalize Strategic Value Selling with structured playbooks, AI-assisted call review tools, and inspection cadences.
  • Own the enablement content ecosystem, including messaging frameworks, playbooks, competitive battlecards, training assets, and partner materials.
  • Lead and scale the Enablement organization, steward the budget, and shape policies, processes, and best practices across the sales and marketing organization.

Requirements

  • 12+ years of progressive experience in sales enablement, sales productivity, or GTM strategy within enterprise B2B SaaS.
  • A 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 conviction that AI changes how sales organizations learn and execute.
  • Strong analytical ability, including defining metrics, building dashboards, and using data to diagnose performance gaps.
  • Ability to partner with and influence senior leaders across Sales, Marketing, Product, and Customer Success.
  • Execution-oriented mindset, with comfort both setting strategy and building programs hands-on.
  • Outstanding communication skills and executive presence for senior GTM audiences.
  • Bachelor’s degree required; MBA or advanced degree preferred.
  • Experience in a PE-backed or sponsor-backed environment is preferred.
  • Background in AI enablement or future-of-work strategy, especially in organizations deploying AI/ML into products or GTM motions is preferred.
  • Prior experience at SaaS or enterprise software companies undergoing major product or GTM transitions is preferred.
  • Familiarity with enterprise sales methodologies such as Value Selling, Challenger, or equivalent is preferred.

Benefits

  • US base salary range of $187,500 to $247,500.
  • Eligible for a market-competitive incentive opportunity.
  • Employer-subsidized medical, vision, and dental coverage for full-time employees.
  • 401(k) match at 50% of your contribution up to the first 6% of eligible pay.
  • Monthly stipend to support work and productivity.
  • Flexible Time Away Program plus Sick Time Off.
  • Up to 24 weeks of parental leave.
  • 12 paid holidays per year for US employees.
  • Teleworking options from any registered U.S. location for role-specific positions.
  • Access to professional growth and development resources, including Udemy online courses.
  • Company-funded perks including a counseling membership, local retail discounts, and a personal Smartsheet account.

Interested in this position?

Apply directly on the company website

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