Sales Enablement Learning Partner - Expansion Sales

<div class="content-intro"><p style="line-height: 1.2;">&nbsp;</p> <hr> <p><strong>About Gusto</strong></p> <p>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.</p> <p>&nbsp;<br>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. Learn more about our<a href="https://gusto.com/about/careers/total-rewards" target="_blank"> <u>Total Rewards philosophy</u></a>.</p> <p>&nbsp;<br>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.</p></div><p><strong>About the Role:</strong></p> <p>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.</p> <p>We are seeking an individual with expertise in learning science, strong consulting capability, and experience in professional sales or business development. You are passionate about enabling Expansion Sellers (upsell/cross-sell/renewal revenue motions) with the content, tools, insights, and training they need to win more business while exceeding the expectations of our existing clients. You align with our company values, are highly self-motivated to drive results, and bring a relentless curiosity to continuously deepen product knowledge and scale enablement at pace in a fast-moving environment.</p> <p><strong>Here’s what you’ll do day-to-day:</strong></p> <ul> <li>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</li> <li>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.</li> <li>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.</li> <li>Define and track KPIs to measure the impact of enablement initiatives, including time-to-performance, and use data to quickly iterate and refine solutions.</li> <li>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</li> <li>Partner cross-functionally to ensure enablement content remains current and optimized for seller workflows, even as priorities and product capabilities evolve quickly</li> <li>Cultivate a community of expert practitioners, crowdsourcing best practices and user-generated content to continuously improve enablement</li> <li>Monitor industry trends and competitive dynamics, adapting enablement priorities quickly as business needs change</li> <li>Research and apply emerging AI tools and methodologies to accelerate design, development, and delivery while maintaining quality and effectiveness.</li> </ul> <p><strong>Here’s what we're looking for:</strong></p> <ul> <li>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.</li> <li>Proven track record of designing and delivering highly effective enablement programs that drive measurable improvements in sales performance and productivity</li> <li>Demonstrate