Sales Enablement Learning Partner, PEO & Business Insurance · Gusto

Sat, 25 Apr 2026 20:50:51 GMT
Sales

Gusto · Denver, CO;San Francisco, CA;New York, NY;Las Vegas, NV;Atlanta, GA;Chicago, IL;Phoenix, AZ · $177,000 - $200,000 in San Francisco, CA; New York, NY $150,000 - $170,000 in Denver, CO; Phoenix, AZ; Atlanta, GA; Chicago, IL · hybrid

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. 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.

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.

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 we're 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