Head of Benefits, New Segments

Gusto is hiring a seasoned product management leader with 6+ years of experience in operationally complex domains.

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 200,000 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.

You’ll be leading the pursuit of our critical, new customer segment (mid-sized and growing businesses) for Gusto. Your mission is to craft a vision and product roadmap for one of our most profitable and attractive product offerings, Benefits & Total Rewards. This product area is critical for this new segment to thrive by attracting, caring-for and retaining talent. This role will begin as an individual contributor with the expectation to build out multiple teams over time. 

When you join, you’ll hit the ground running with a dedicated and growing team of Design, Engineering, and Data Science partners.

Here’s what you’ll do day-to-day:

  • Drive the roadmap for delivering and guiding small and mid-sized businesses on how to optimally offer benefits and rewards specific to their business and team across the country, and the globe. 
  • Research and develop a vision for a best-in-class broker experience (a new user and new channel for Gusto).
  • Build a vision for how Gusto invests in benefits for the long-term including investments in large-group health insurance, PEO, level-funded health plans, and 401k. 
  • Build business cases for expanding our benefits offerings and new teams in support of that vision. 
  • Be an owner of products and businesses – end to end.
  • Identify emerging opportunities and industry trends, build business cases, and define product vision and strategy.

Here’s what we're looking for:

  • 6+ years of hands-on product management & leadership experience.
  • Entrepreneurial, driven, passionate about our mission, and have deep empathy for our customers.
  • Experience working in ops-heavy spaces.
  • A proven track record of building products 0 → 1 that customers love.
  • The ability to paint a compelling vision to inspire your teams and senior leaders. Ability to articulate and build business models and create a supporting roadmap that rapidly iterates into delivering on your vision.
  • Bonus points if you have experience in complex regulatory domains.

At Gusto, we strive to provide rewards that empower employees to achieve their financial and personal goals. We offer competitive compensation packages with a strong emphasis on equity based compensation (ownership in Gusto). To learn more about Gusto’s compensation philosophy and benefits offerings please view our Total Rewards Approach page.

Our cash compensation range for this role is $154,000/yr to $211,000/yr in Denver & most remote locations, and $187,000/yr to $249,000/yr in San Francisco & New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.

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 need assistance or an accommodation due to a disability, you may contact us at accommodations@gusto.com.

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