Director, Revenue Enablement - Technical Skills Enablement (Remote Eligible)

The Revenue Enablement Director, Technical Skills Enablement leads the Technical Skills track of Role Excellence. You will build and run the strategy that gives Solution Engineers, Customer Success Managers, and Professional Services consultants the platform and solution competence to drive demonstrated customer outcomes. You will be a deeply technical, strategic leader and executive influencer who earns credibility with Product, Engineering, and field leaders alike.

Technical depth is critical to the customer engagement journey, and it is what turns a sold solution into realized outcomes. You will ensure customer-facing teams can competently use AI and FDE solutions and the Smartsheet platform to design, demonstrate, deploy, and optimize solutions with confidence.

This is a build-the-future role, not a maintain-the-program role. We are reshaping how customer-facing teams are prepared to win and retain customers as AI changes how customers buy, evaluate, and use execution management platforms. 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, and lead a team and a set of cross-functional partners to make it real at scale.

In 2005, Smartsheet was founded on the idea that teams and millions of people worldwide deserve a better way to deliver their very best work. Today, we deliver a leading cloud-based platform for work execution, empowering organizations to plan, capture, track, automate, and report on work at scale, resulting in more efficient processes and better business outcomes.

Our mission in GTM Enablement: we build confidence and competence in customer-facing roles so they can deliver customer value and drive revenue and retention.

This Director role reports to the VP of Revenue Enablement.

You Will:

• Own the Technical enablement strategy, hands-on experiences, and reinforcement for customer-facing roles, graduated by role and proficiency: platform and solution competence, technical envisioning, demo and proof of concept, solution design/delivery, product and security narrative, and outcome realization.
• Build a technically authoritative enablement capability and scenario-based assessment, that keeps pace with a rapidly evolving platform and AI portfolio.
• Lead the technical content capability, and partner with Customer Education and Product so internal and customer-facing technical learning are consistent and non-duplicative.
• Drive predictable, role-specific technical skilling for prioritized GTM plays tied to product General Availability, covering pre-, at-, and post-GA moments.
• Collaborate deeply with the Consultative Skills CoE so technical and consultative capabilities are orchestrated seamlessly in customer conversations.
• Equip managers, through the Manager / Leader Enablement CoE, to assess and coach technical proficiency in their teams.
• Drive measurable proficiency outcomes tied to revenue (e.g., technical win rate, deal velocity, solution attach, time to first customer value, adoption, and net retention) and report them to senior leadership.
• Set the strategy and own the outcomes for your Center of Enablement Excellence, translating company OKRs and GTM priorities into a clear multi-quarter roadmap with defined behavior-change and business-impact metrics.
• Operate as a strategic leader and executive influencer: shape priorities with Directors, VPs, and SVPs across Sales, Customer Success, Professional Services, Product, and People, and secure alignment and investment through data and business cases.
• Build and lead a high-performing team; hire, coach, and develop leaders, set a high bar for execution, and foster an inclusive, accountable culture.
• Drive execution with rigor: run a predictable operating cadence, manage budget, headcount, vendors, and priorities, and deliver on commitments at scale across geographies.
• Apply AI and modern learning technology to scale: partner with the AI-Based Content Creation & Experiences CoE and the enablement tech stack to deliver just-in-time, proficiency-aware skilling experiences.
• Partner as one team with fellow CoE Directors to deliver a seamless, end-to-end capability journey, with clean hand-offs and no gaps or duplication for the roles we serve.

You Have:

• 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.
• The ability to translate complex product and architecture concepts for a range of audiences, and to partner credibly with Engineering and Product leaders.
• 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.
• Demonstrated ability to influence and partner with senior and executive stakeholders, including VP and SVP leaders, and to align cross-functional teams without direct authority.
• 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.
• A track record of improving field proficiency and customer outcomes with data.
• 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.