Sales Enablement Learning & Development Partner

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Denver, CO
Hybrid
104K-155K Annually
7+ Years Experience
Fintech • HR Tech
Gusto simplifies HR, payroll & benefits for modern businesses.
The Role


Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 300,000 businesses nationwide.
Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That's why we're committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy .

This role is part of our Sales Enablement team, within our Revenue Operations organization. Our RevOps organization is the linchpin of our world-class sales experience. As a key contributor, you will play a critical role in executing strategy to drive revenue growth across health insurance/benefit sales. We are looking for a sales enablement expert who is passionate about supporting benefit sellers with the learning content, tools, insights, and training to help them win more businesses while exceeding client expectations. Candidates should align with our company values, be highly self-motivated to drive results, and have an insatiable desire to learn and grow to maintain deep product knowledge and scale enablement at pace in a fast-moving environment. .

  • Partners with the relevant stakeholders and leadership to develop and execute a strategic vision for benefit sales enablement that elevates the capabilities of our sellers
  • Collaborate closely with Revenue, RevOps and partners to deeply understand our use-cases, solutions and technical requirements to provide targeted enablement
  • Establish KPIs and analytics to track the impact of enablement initiatives, including TTP (time to performance), and to make data-driven decisions
  • Design and deliver comprehensive onboarding programs, ongoing training, and just-in-time learning resources to keep our benefits sales teams on the cutting edge
  • Identify skill and knowledge gaps, then partner cross-functionally to build innovative enablement programs that drive measurable improvements in capability, productivity, and revenue generation using instructional (live and e-learning) and non-instruction methods
  • Partner with cross functional teams to ensure enablement content is always up-to-date and optimized for sellers
  • Cultivate a community of expert practitioners, crowdsourcing best practices and user-generated content to continuously improve enablement
  • Stay on the pulse of industry trends and competitive landscapes, adapting enablement priorities as needed



  • 8+ years of sales enablement, training and sales/sales management experience ideally in the health insurance or benefits field
  • Proven track record of designing and delivering highly effective enablement programs that drive measurable improvements in sales performance
  • Demonstrated ability to lead and manage new learning and development projects from needs analysis to post-delivery evaluation with multiple competing priorities
  • Experience designing and facilitating new hire training and continuous education training for a high volume call center environment with positive outcomes
  • Excellent analytical, communication and presentation skills, with expertise in engaging stakeholders and working cross-functionally to build productive relationships that ensure learning objectives and content lead to optimal learning outcomes
  • Knowledge of instructional design principles including adult education concepts to identify appropriate delivery methods and develop technical and conceptual content
  • Experience with content creation, curation, and knowledge management platforms balanced with a true passion for sales: you find creative ways to make sales teams more productive
  • Conflict resolution skills and a personality that thrives in a dynamic environment. Ability to handle - and even thrive - in an urgent and ambiguous environment with grace and composure
  • This role has a travel requirement with potential travel of 15% of the year



  • License - Health and Life Insurance Producer License in resident state
  • An advanced degree or certificate in enablement
  • Experience with GSuite, a Mac, Salesforce, Slack, Asana, NICECXOne along with various learning management systems and authoring tools


Our cash compensation amount for this role is targeted at $127,000 - $155,000 in San Francisco and New York, and $104,000 - $128,000 in Denver and most remote locations. 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 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.
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 it's 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. If you require assistance in filling out a Gusto job application, please reach out to [email protected].

What the Team is Saying

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The Company
Denver, CO
2,344 Employees
Hybrid Workplace
Year Founded: 2012

What We Do

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 300,000 businesses.

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 it's 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.

Why Work With Us

When you join Gusto, you become part of a diverse and passionate community dedicated to empowerment, innovation, and providing meaningful solutions. Join us in building a world where work truly empowers a better life. Build with Gusto!

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Gusto Offices

Hybrid Workspace

Employees engage in a combination of remote and on-site work.

The workplace may be changing, but our team is stronger than ever. Whether you are near our offices (SF, Denver, NYC) or work remotely from one of our hub cities like LA or Las Vegas, we want employees to feel as productive and connected as possible!

Typical time on-site: 2 days a week
Denver, CO

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