Benefits Advising (Renewals) Leader

🏢 Gusto · 📍 Denver, CO - Hybrid · 💼 hybrid 💰 $86,530 - $86,530 / yr

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Position Summary & Responsibilities

About Gusto

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. With teams in Denver, San Francisco, and New York, 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. Learn more about our Total Rewards philosophy.

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.

About the Role:

Gusto is seeking a leader for our Benefits Advising team who is passionate about providing small business owners and their employees with the best customer experience and expert benefits advice. You will lead a licensed benefits advisor organization by empowering and enabling your individual contributors to deliver a best in class customer experience effectively in a fast paced environment. You’ll be a great fit if you also have experience in effectively managing OKR/team initiatives while also leading a high performing team.

About the Team:

The Benefits Advising team at Gusto is focused on understanding the health insurance needs of small businesses, and consulting on solutions to help their employees thrive. The Benefits Advising leader will empower a team in Gusto’s licensed advising renewal organization, ensuring our customers offer the best health insurance and benefits offerings for their employees. This role will balance both customer impact and operational excellence: you’ll be responsible for driving customer retention, expansion, and exceptional customer experience at scale.

Your team will support small business owners in accessing the best health insurance and holistic benefits offerings - including ancillary coverage, tax-advantaged accounts, and re

🎯 Candidate Preparation Guide For Gusto Applicants

Key Role Competencies & Evaluation Highlights

Key Role Focus:

Complex regulatory domain expertise, financial accuracy, empathetic employee experience, and collaborative craftsmanship.

📋 Preparation Priorities (Key Areas to Clarify):

1. Treating financial or payroll data structures casually, missing edge cases in state, time zones, or tax laws.
2. Exhibiting arrogance toward non-technical stakeholders or regulatory partners.
3. Writing fragile codebases that lack automated testing, audit trails, and immutability where needed.

✨ Recommended Role Alignment Hook:

I build human-centric financial infrastructure that automates complex compliance so small businesses can focus on their people.

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