Sales Enablement Learning Partner - Expansion Sales · Gusto

Sat, 25 Apr 2026 21:03:16 GMT
Sales

Gusto · Denver, CO;San Francisco, CA;New York, NY;Las Vegas, NV;Atlanta, GA;Chicago, IL;Phoenix, AZ · Competitive salary and benefits package · hybrid

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff , payroll, health insurance, 401(k)s, and HR , so owners can focus on their craft and their customers.

With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) , because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

About the Role: The Sales Enablement team sits within our Revenue Operations organization, the linchpin of our world-class sales experience. Learning Partners play a critical role in executing enablement strategies to drive revenue growth and feature adoption across sales.

This role owns the learning lifecycle for Expansion Sales and partners closely with leaders on onboarding, continuous education, and high-performance skill development. You will design and implement learning solutions that include high-impact learning assets, self-paced content, and facilitated experiences.

We are seeking an individual with expertise in learning science, strong consulting capability, and experience in professional sales or business development.

Responsibilities:

Collaborate with stakeholders and partners including revenue, revenue operations and other cross functional leads to determine sellers learning and performance needs and priorities to achieve business results

Diagnose skill and knowledge gaps and independently design and deliver enablement solutions that drive measurable improvements in capability, productivity, and revenue,often with limited information, tight timelines, and minimal support.

Apply learner-centered design principles while balancing speed, pragmatism, and impact, tailoring solutions based on observation, stakeholder input, and the depth of learning required for performance.

Define and track KPIs to measure the impact of enablement initiatives, including time-to-performance, and use data to quickly iterate and refine solutions.

Design, build, and deliver onboarding, continuous training, and just-in-time learning experiences with a bias toward action, rapid development, and scalable execution to keep our expansion sales teams on the cutting edge

Partner cross-functionally to ensure enablement content remains current and optimized for seller workflows, even as priorities and product capabilities evolve quickly

Cultivate a community of expert practitioners, crowdsourcing best practices and user-generated content to continuously improve enablement

Monitor industry trends and competitive dynamics, adapting enablement priorities quickly as business needs change

Research and apply emerging AI tools and methodologies to accelerate design, development, and delivery while maintaining quality and effectiveness

Requirements:

8+ years of experience in sales enablement, training, or sales leadership supporting multi-product sales and expansion revenue motions (upsell, cross-sell, renewals), ideally in a high-volume environment.

Proven track record of designing and delivering highly effective enablement programs that drive measurable improvements in sales performance and productivity

Demonstrated ability to independently lead learning initiatives end-to-end, from needs analysis through delivery and post-program evaluation, while managing multiple competing priorities.

Experience designing and facilitating new hire training and continuous education training for expansion/customer success/retention teams focused on growth

Strong analytical, communication, and presentation skills, with the ability to influence stakeholders and work cross-functionally to ensure learning objectives translate into real performance outcomes

Solid foundation in instructional design and adult learning theory, with the judgment to select appropriate modalities based on speed, scale, and impact

Hands-on experience with content creation, curation, and knowledge management platforms, paired with a genuine passion for sales and finding creative ways to make sellers more effective

Comfort operating in urgency and ambiguity, with the resilience, conflict management skills, and composure required to thrive in a fast-paced environment

Preferred Qualifications:

Knowledge of the payroll industry

An advanced degree or certificate in enablement, education or organizational science

Experience with GSuite, a Mac, Salesforce, Slack, Notion, AI tools along with various learning management systems and authoring tools

Salary and Benefits:

Our cash compensation amount for this role is $108,570 to $163,500 for Denver, Atlanta, Chicago & Las Vegas. $131,430 to $192,500 for San Francisco & New York. $102,040 to $163,500 for Phoenix. Final offer amounts are determined by multiple factors including candidate location, 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.

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.

Gusto takes security and compliance very seriously. Please note that certain positions at Gusto may require background checks and/or credit checks as a condition of employment.

If you're excited about this role and want to learn more, please don't hesitate to reach out to us. We can't wait to hear from you!