Sales Enablement Learning Partner, PEO & Business Insurance

Company: Gusto
Location: Schiller Park
Posted on: March 27, 2026

Job Description:

At Gusto, were 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 . 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 business insurance products (e.g., Workers’ Comp, BOP, Commercial Auto, E&O) and PEO 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 HR solution sellers 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. 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 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 were looking for: 12 years of experience in sales enablement, training, or sales leadership supporting high-volume HR solution sales, ideally in PEO or licensed business insurance sales (EG: Workers’ Comp, BOP, Commercial Auto, E&O). 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 licensed sales 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 GSuite, Salesforce, Slack, Notion, AI tools along with various learning management systems and authoring tools Our cash compensation amount for this role is targeted at: $177,000 - $200,000 in San Francisco, CA; New York, NY $150,000 - $170,000 in Denver, CO; Phoenix, AZ; Atlanta, GA; Chicago, IL If you are outside of the geographic areas above, your application will not be considered at this time. 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, Gustos 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 its 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.

Keywords: Gusto, Mount Prospect , Sales Enablement Learning Partner, PEO & Business Insurance, Sales , Schiller Park, Illinois