Director, Revenue Enablement – Technical Skills Enablement

Smartsheet Prospects; Bellevue (WA); Remote; USD 170,000 - 260,000; Full time

Benefits offered by this job

Medical and vision coverage

Dental coverage

401k match

Monthly stipend

Flexible time away

Paid holidays

Job summary

RevOps Careers seeks a Director, Revenue Enablement - Technical Skills Enablement to lead the Technical Skills track and shift enablement from event-based to always-on, proficiency-aware skilling aligned with product launches.

The role demands strong executive communication, global program leadership, and a track record of building competency-based enablement with measurable impact on revenue metrics.

Qualifications

• 12+ years of enablement, learning and development, or related experience in a high-growth SaaS or tech company
• 6+ years leading managers or senior ICs with a track record of building high-performing teams
• Technical credibility in SaaS, work management, automation, or enterprise platforms
• Experience designing hands-on technical learning, certification, and validation programs at scale
• Ability to translate complex product and architecture concepts for diverse audiences and partner with Engineering/Product
• Proven strategic thinking and execution turning an ambiguous vision into a measurable program
• Experience building programs on competency or proficiency frameworks using data linked to outcomes
• Proven record of leading teams in sales-focused, metric-driven environments (ARR, Pipeline)
• Experience building AI and FDE solution fluency across SE/CS/PS roles to drive outcomes
• Strong command of adult learning principles, enablement tech, and AI-enabled delivery
• Executive communication, storytelling, and action-biased leadership in fast-moving settings
• Experience managing budgets, vendors, and global programs across time zones
• BA/BS required; MBA or advanced degree preferred, or equivalent experience

Responsibilities

• Own the Technical enablement strategy, hands-on experiences, and reinforcement for customer-facing roles, graduated by role and proficiency
• Build a technically authoritative enablement capability and scenario-based assessment aligned to a rapidly evolving platform and AI portfolio
• Drive role-specific technical skilling for prioritized GTM plays tied to product launches and GA moments
• Equip managers to assess and coach technical proficiency via the Manager / Leader Enablement CoE
• Partner credibly with Engineering and Product leaders to translate complex concepts for diverse audiences
• Lead data-driven programs linking enablement investment to business outcomes across time zones

Skills

Leadership experience

Strategic thinking

Data-driven decision making

Executive communication

AI-enabled content delivery

Budget management

Global program management

Cross-functional collaboration

Adult learning principles

Problem solving

Education

BA/BS

MBA or advanced degree preferred

Job description

Role Overview

The Director, Revenue Enablement - Technical Skills Enablement leads the Technical Skills track of Role Excellence. This is a build-the-future role, not a maintain-the-program role, where you will define the strategic, future capabilities of your Center of Enablement Excellence, moving from event-based enablement to always-on, data-driven, proficiency-aware skilling measured by revenue attainment.

What You Will Do

You will own the Technical enablement strategy, hands-on experiences, and reinforcement for customer-facing roles, graduated by role and proficiency. You will build a technically authoritative enablement capability and scenario-based assessment, that keeps pace with a rapidly evolving platform and AI portfolio.

Why It Might Be a Fit

You will drive predictable, role-specific technical skilling for prioritized GTM plays tied to product General Availability, covering pre-, at-, and post-GA moments. You will equip managers, through the Manager / Leader Enablement CoE, to assess and coach technical proficiency in their teams.

Requirements

• 12+ years of experience in enablement, learning and development, sales or customer-facing operations, or a closely related discipline in a high-growth SaaS or technology company
• 6+ years of experience leading managers and/or senior individual contributors, with a record of building, developing, and retaining high-performing teams
• Technical credibility in SaaS, work management, automation, or enterprise platforms, ideally from experience leading or building solution engineering, customer success, or professional services teams
• Experience designing hands-on technical learning, certification, and validation programs at scale
• Ability to translate complex product and architecture concepts for a range of audiences, and to partner credibly with Engineering and Product leaders
• Proven strategic thinking and execution: a history of turning an ambiguous vision into a scaled, measured program that changed behavior and moved business results
• Experience building programs on a competency or proficiency framework, and using data to link enablement investment to business outcomes (required)
• Proven record of leading teams and working in environments strongly focused on sales and metric driven roles (e.g., ARR, Pipeline)
• Prior success building AI and FDE solution fluency across SE, CS, and PS roles to drive measurable business outcomes
• Strong command of adult learning principles, modern enablement technology, and AI-enabled content and delivery
• Executive-level communication, storytelling, and presentation skills, with sound judgment and a bias to action in a fast-moving environment
• Experience managing budgets, vendors, and global programs across time zones
• BA/BS required; MBA or advanced degree preferred, or equivalent experience

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
• US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans
• US employees receive 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)

Read by ReLoop.me

A director-level owner of technical enablement for customer-facing roles, tasked with replacing event-based training with always-on, proficiency-aware skilling tied to product launches.

Shape of the role: strongly build / define; leans strategy.

Core capabilities: Technical enablement strategy ownership, competency or proficiency framework design and scenario-based technical assessment design.

Indicative, AI-generated read, no salary range. Full read and sourcing ReLoop.me

Tagged as: Data Analysis, Pipeline Management