About Gusto

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

The Legal & Compliance team is seeking an experienced health insurance compliance professional to oversee broker practices related to the digital insurance space. This position is a hybrid role that will be based in either our San Fransisco or Denver office. 

In this role, you will be an experienced insurance specialist for Gusto’s benefits products, playing an integral part in all things benefits (primarily supporting the health and life product lines across small group, individual, and embedded). A “go to” partner when collaborating with key stakeholders across the enterprise to help deliver innovative business solutions focused on product development and design, sales, and administration of such insurance products as well as issues related to agency regulatory practices. You will report directly to the Head of Benefits Compliance. As a leader on this team, you will also be seen as an advocate for advancing our alignment with the business, driving team outcomes, and inspiring and mentoring colleagues to continually develop.

We’re looking for someone who is detail-oriented, and has a passion to build, who would enjoy working collaboratively with the Compliance team. We are passionate about using innovative technology and excellent service to elevate the health and benefits experience of small business owners and their employees. Each team member is a true owner and makes a tremendous impact every day. You will use your curiosity, sharp attention to detail, knack for problem solving to streamline compliance and ensure that our internal processes keep us and our Gustomers safe.

The ideal candidate thrives on working cross-functionally, building trust across a number of functions, and is an efficient multitasker.

Here’s what you’ll do day-to-day:

  • Investigate issues, perform research, and help document processes that are subject to state and federal insurance regulatory requirements, such as PPACA, HIPAA, and other HHS, DOL, IRS and state insurance requirements.
  • Review commissions, rebates, and other regulatory requirements in relation to operations and sales processes
  • Be a knowledge partner! Research, document, and educate others on updates related to internal process, external policy, and best practices with a focus on scaling operations and compliance maturity cross functionally. 
  • Constantly analyze, refine, and iterate on internal processes to make them simpler and more efficient.
  • End of year readiness and execution to support high-touch and fast-paced issue resolution to keep Gusto and our Gustomers safe.

Here’s what we're looking for:

  • 4+ years of experience in an health insurance advisory role or in the compliance industry
  • Deep knowledge of insurance regulations, including but not limited to those issued by regulatory bodies such as NAIC and state insurance departments
  • Demonstrated track record of working under a brokerage firm on regulatory compliance matters including, but not limited to: producer advising, complaints handling, carrier underwriting, health and welfare plan obligations, brokerage conduct risk.
  • Excellent knowledge of federal and state laws and regulations applicable to insurance operations.
  • Proven ability to interpret and apply regulatory requirements to business practices effectively.
  • Excellent written and presentation communication skills.
  • Ability to translate and apply regulatory requirements for consumption by technical and non-technical audiences
  • Approach problems with a passion for reducing operational inefficiencies and pain points
  • Ability to adapt quickly to evolving program needs
  • Enjoy working collaboratively with cross-functional teams

Nice to haves:

  • Experience in Compliance Risk Management frameworks such as Policy Development and Training, Regulatory Compliance, Monitoring and Reporting and can apply these activities to compliance processes
  • Regulatory experience or interest in regulatory compliance
  • Project management
  • Self-direction and a knack for spotting issues and solving problems

Our cash compensation range for this role is $91,000/yr to $107,000/yr in Denver and $111,000/yr to $130,000/yr in San Francisco & New York. Final offer amounts are determined by multiple factors, including candidate location, experience and expertise, and may vary from the level and 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.


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 candidate-accommodations@gusto.com.

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Our customers come from all walks of life and so do we. We hire people from a wide variety of backgrounds, not just because it’s the right thing to do, but because it helps us to build better products, better serve our customers, and makes our company stronger. 

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