Sales Enablement Specialist

Sales Enablement Specialist

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we're proud to support more than 400,000 small businesses across the country, and we're building a workplace that represents and celebrates the customers we serve.

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.

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, Gusto's 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 it's 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.