Sales Enablement Learning Partner - Expansion Sales

Gusto • Chicago, NY

12d • $102,040 - $192,500 • Hybrid

About The Position

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. Learn more about our Total Rewards philosophy . 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. 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.

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
• Willingness to travel up to 20% annually

Nice To Haves

• 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

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees