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. Here’s what we're looking for: 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 Preferred Qualifications: Knowledge of the payroll industry An advanced degree or certificate in enablement, education or organizational science Experience with G - Suite, a Mac, Salesforce, Slack, Notion, AI tools along with various learning management systems and authoring tools 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.