Director, Revenue Enablement – Technical Skills Enablement

This is a fully remote position, open to applicants in Washington.

📋 Description

• Oversee the Technical Skills track of Role Excellence for Solution Engineers, Customer Success Managers, and Professional Services consultants.

• Develop and implement the technical enablement strategy, including hands-on experiences, reinforcement, and scenario-based assessments across various roles and proficiency levels.

• Ensure customer-facing teams effectively utilize AI, FDE solutions, and the Smartsheet platform to design, demonstrate, deploy, and optimize solutions.

• Lead the development of technical content capabilities, collaborating with Customer Education and Product teams to align both internal and customer-facing technical learning initiatives.

• Drive role-specific technical skill development for prioritized go-to-market strategies surrounding product General Availability.

• Work alongside the Consultative Skills CoE to integrate technical and consultative competencies in customer engagements.

• Prepare managers to evaluate and coach technical proficiency.

• Measure and report proficiency outcomes related to revenue, including metrics such as technical win rate, deal velocity, solution attachment, time to first customer value, adoption, and net retention.

• Establish strategy and own outcomes for the Center of Enablement Excellence, converting company OKRs and GTM priorities into a multi-quarter roadmap.

• Influence Directors, VPs, and SVPs across Sales, Customer Success, Professional Services, Product, and People to ensure alignment and secure investment.

• Build and lead a high-performing team by hiring, coaching, and developing future leaders.

• Manage operating cadence, budget, headcount, vendors, priorities, and global execution.

• Leverage AI and modern learning technologies to scale just-in-time, proficiency-aware skill development experiences.

• Collaborate with other CoE Directors to deliver a comprehensive capability journey.

• Report directly to the VP of Revenue Enablement.

⛳️ Requirements

• Possess technical credibility in SaaS, work management, automation, or enterprise platforms, ideally from experience in leading or building solution engineering, customer success, or professional services teams.

• Demonstrated experience in designing hands-on technical learning, certification, and validation programs at scale.

• Ability to simplify complex product and architecture concepts for diverse audiences and partner effectively with Engineering and Product leaders.

• 12+ years of experience in enablement, learning and development, sales or customer-facing operations, or a closely related discipline within a high-growth SaaS or technology company.

• 6+ years of experience managing managers and/or senior individual contributors, with a proven track 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 align cross-functional teams without direct authority.

• Proven strategic thinking and execution skills, including the ability to transform an ambiguous vision into a scalable, measurable program that drives behavioral change and business results.

• Experience in developing programs based on a competency or proficiency framework and utilizing data to connect enablement investments to business outcomes (required).

• Proven success in leading teams and working in environments that prioritize sales and metrics-driven roles (e.g., ARR, Pipeline).

• Track record of enhancing field proficiency and customer outcomes through data-driven approaches.

• Strong understanding of adult learning principles, modern enablement technology, and AI-enabled content and delivery methods.

• Exceptional executive-level communication, storytelling, and presentation skills, coupled with sound judgment and a proactive approach in a fast-paced environment.

• Experience managing budgets, vendors, and global programs across different time zones.

• BA/BS degree is required; MBA or advanced degree preferred, or equivalent experience.

🏝️ Benefits

• Employer-subsidized medical, vision, and dental coverage for full-time employees.

• 401k Match to assist you in saving for your future (50% of your contribution up to the first 6% of your eligible pay).

• Monthly stipend to enhance your work and productivity.

• Flexible Time Away Program, in addition to Sick Time Off.

• US employees automatically receive coverage under Smartsheet-sponsored life insurance, short-term, and long-term disability plans.

• US employees enjoy 12 paid holidays each year.

• Up to 24 weeks of Parental Leave.

• One personal paid Volunteer Day to contribute to our community.

• Opportunities for professional growth and development, including access to Udemy online courses.

• Company-funded perks, such as a counseling membership, local retail discounts, and your personal Smartsheet account.

• Teleworking options from any registered location in the U.S. (specific to the role).

• Competitive market incentive opportunities.