Sales Enablement Specialist

Sales Enablement Specialist
The Sales Enablement team equips sellers with the skills, product knowledge, and tools required to perform effectively across the Gusto customer journey. As a Sales Enablement Specialist, you will design and facilitate onboarding and continuous education programs that drive seller readiness and productivity. This role partners closely with Sales Leadership and Revenue Operations to deliver high-impact learning experiences aligned to business priorities. The ideal candidate has demonstrated experience facilitating new hire and ongoing sales training in a high-volume environment; experience in payroll or HR technology is preferred.

The Role

Sales Enablement sits within Revenue Operations and partners closely with Sales Leadership to drive seller productivity and performance. In this role, you will design and facilitate learning experiences across sales methodology, product knowledge, and core systems. You will also serve as the enablement lead for a defined product line, owning the end-to-end learning strategy and execution for the sales team that supports it — from needs analysis and curriculum design through facilitation, measurement, and continuous improvement.

Here’s What You’ll Do

Facilitation & Delivery

• Deliver high-impact training through in-person, virtual, and blended formats across onboarding and ongoing skill development initiatives.


• Facilitate sessions that build sales methodology, product expertise, and systems (AI and Sales Ops tools) proficiency for IC sellers and frontline leaders.


• Ensure a seamless learner experience by managing classroom logistics, communications, and materials.


• Maintain certification and deep working knowledge of assigned product and sales content.

Product Enablement Ownership

• Serve as the enablement lead for a defined, revenue-generating product sales team, owning the end-to-end design, delivery, and optimization of that program.


• Conduct independent needs analysis to identify skill gaps and performance opportunities aligned to revenue goals.


• Partner with Sales Leadership and Revenue Operations to align enablement priorities with quarterly business objectives.


• Lead quarterly curriculum refresh cycles — or update content as needed — to reflect product updates, competitive insights, and evolving sales strategies.


• Track program effectiveness using learner feedback and performance indicators; iterate content to improve seller readiness and results.

Instructional Design & Continuous Improvement

• Design and update learning assets (facilitator guides, role plays, job aids, assessments) aligned to defined learning and performance outcomes.


• Collaborate with subject matter experts and cross-functional partners to ensure content accuracy and business relevance.


• Maintain structured and accessible enablement resources within learning and knowledge management systems.

Here’s What We’re Looking For

• 5+ years of experience in sales training, enablement, or sales roles within a high-volume environment.


• Demonstrated experience designing and facilitating onboarding and ongoing sales training programs.


• Ability to independently conduct needs analysis and translate business requirements into structured learning experiences.


• Working knowledge of instructional design principles and adult learning theory; ability to select appropriate modalities to achieve defined learning outcomes.


• Experience supporting revenue-generating teams and aligning enablement initiatives to performance goals.


• Strong stakeholder management skills; able to partner effectively with Sales Leadership and cross-functional teams.


• Excellent written and verbal communication skills, including comfort facilitating sessions with senior stakeholders.


• Highly organized with the ability to manage multiple concurrent initiatives, quarterly refresh cycles, and competing priorities.


• Proven ability to operate effectively in a fast-paced, evolving environment where priorities shift and information may be incomplete.


• Proficiency with Salesforce, AI-enabled productivity tools, collaboration tools (e.g., Google Workspace, Slack), and learning technologies or authoring tools.


• Willingness to travel up to 20% of the time (approximately one week per month).

Our cash compensation amount for this role is targeted at $111,490 - $131,000 in San Francisco and New York, and $91,915 - $108,000 in Denver and most remote locations. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.