Sales Enablement Specialist

About Gusto

At Gusto were on a mission to grow the small business economy. We handle the hard stufflike payroll health insurance 401(k)s and HRso owners can focus on their craft and customers. With teams in Denver San Francisco and New York were proud to support more than 400000 small businesses across the country and were building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy.

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 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.

Heres What Youll 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.

Heres What Were 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 $111490 - $131000 in San Francisco and New York and $91915 - $108000 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.

Gusto has physical office spaces in Denver San Francisco and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles Gustos subsidiary whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office a secure reliable and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because its the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race color religion national origin age sex (including pregnancy childbirth or related medical conditions) marital status ancestry physical or mental disability genetic information veteran status gender identity or expression sexual orientation or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories consistent with applicable federal state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey please fill out this form and a member of our team will get in touch with you.

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