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Head of Benefits Sales reports to our Head of Expansion (responsible for how Gusto maximizes our opportunity to serve our customers through multi-channel interactions). This leader will empower a team of Employee Benefits advisors serving Gusto’s People Platform customers.

You will be responsible for building and elevating teams that build relationships with Gusto’s customers to deeply understand their needs for Employee Benefits offerings, guide customers through the selection process across all product lines, and aid customers in buying and configuring what maximizes their value within their budget.

You’ll start with a team of ~50 Health Insurance agents selling Gusto’s Small Group Health Insurance to our customers. You’ll expand the remit to arrive at a full-stack Employee Benefits offering to our customers. You’ll have partners in our product, finance, people, and other organizations to develop and execute the plan to turn our monoline, single market segment offering into a robust solution for diverse SMB needs including different health insurance products, ancillary lines, retirement/financial benefits, and more.

You’ll be a member of Gusto’s Revenue team, and our Expansion team specifically. While our craft is revenue generation including sales, the way we generate revenue is through identifying optimal offerings custom targeted for our customers. Our role in Expansion specifically is to extend the lifetime value of our customers by maximizing the value they’re getting from us within their willingness to pay and targeting their most strategic need; we think about extending lifetimes through right-sizing offerings as we do about annual contract value or up-sell maximization.

This is an inside sales team today and likely to remain that way for at least the next couple years. Our teams leverage the new and existing SMBs using the Gusto People Platform (>300k) and can engage customers at any point in their lifecycle with us. Our motions include bundled sales with our Platform team (new Gusto customers), sales during onboarding, and cross-sell opportunities. At current, we generate leads for our sales teams but also enable them to own a book of potential business.

This role is right for you if you have confidence you can empower the team we describe today while charting the course for transformation, and leading us on that path. You will have both input into and accountability for revenue and customer growth targets.

Key responsibilities

• Revenue and customer growth for Gusto Benefits business
• Sales team management
• Input into and collaboration enhancing our product offering. Input into and collaboration understanding industry and competitive trends.
• Deep collaboration with our SMB and insured customer-facing and operational teams
• Ensure short- and long-term growth through effective sales approach consistent with Gusto’s full economic priorities and customer value orientation
• Performance reporting, analysis, forecasting and planning

Experience

• Minimum ten (10) years experience in employee benefits industry with specific sales leadership experience (2nd line or higher)
• Prior experience directly advising employee benefits to SMBs in sales, marketing, or renewal roles

Additional Requirements

• Health and Life producer’s license
• Strong knowledge of employee benefits product lines and industry

Location and Travel

Gusto has physical office spaces in Denver, San Francisco, and New York City. All Gusto roles posted in these metro areas come with the expectation of working from the office on designated days approximately 2-3 days per week (or more depending on role and business travel expectations). 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 role would include travel (~1x/month).

Compensation

Our compensation range for this role is $210,000 to $250,000 OTE (on target earnings) with a 60/40 split between base salary and variable target (60% base / 40% variable) in Denver and most remote locations and $236,000 - $265,000 in San Francisco and New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.