Manager of Health Insurance Renewals Team

Gusto, Inc.•Denver, CO

7d•$86,530 - $113,000

About The Position

Gusto is seeking a Manager for its Health Insurance Benefits Advising team. The role leads a licensed benefits advisor organization, empowering individual contributors to provide small business owners and their employees with expert benefits advice and an excellent customer experience in a fast-paced environment. The manager leads 10–15 licensed advisors and specialists through renewal cycles, balancing customer impact with operational excellence and driving retention, expansion, and exceptional customer experience at scale. The team advises small businesses on health insurance and holistic benefits, including ancillary coverage, tax-advantaged accounts, and retirement plans such as 401(k)s. Much of its work concerns small-group health insurance, including fully insured and level-funded plans. The manager coaches and manages performance, improves renewal experiences and processes, leads cross-functional initiatives and change management, builds team engagement, and partners with Product, Carrier Ops, Sales, and other customer experience teams. The role also champions strategic AI adoption to improve advisor productivity and customer engagement while maintaining compliance and customer trust. Gusto offers competitive base pay, benefits, and equity (RSUs) to full-time employees. Cash compensation is $86,530–$106,000 per year in Phoenix and $92,245–$113,000 per year in Denver, Chicago, and Las Vegas. Employees based in Gusto office locations are expected to work in-office on designated days approximately 2–3 days per week or more depending on role. Approved work from non-office locations requires a secure, reliable, consistent internet connection and regular, predictable attendance. Gusto has offices in Denver, San Francisco, and New York City; Symmetry roles are subject to office expectations at its Scottsdale office.

Requirements

4–6 years of formal leadership experience in benefits advisory, customer success, renewals, or a similar field.
Direct experience with small-group health insurance, including fully insured, level-funded, or PEO models.
Demonstrated ability to drive revenue growth, customer retention, and expansion through consultative renewal and upsell strategies.
Analytical and strategic thinking, including the ability to translate data into insights and actions.
Strong operational skills, a proactive approach to process improvement, and experience driving initiatives and best practices that improve customer experience.
Ability to evaluate and adopt AI tools strategically to measurably improve advisor productivity, customer retention, and operational efficiency while balancing risk management, compliance, and customer trust in a licensed advisory context.
Experience with technology and automation solutions such as Salesforce, APIs, and benefits administration platforms.
Executive presence and ability to align leaders across Customer Experience, Sales, and Product and lead high-impact initiatives.
Customer-first mentality and a first-principles-thinking approach.
Ability to lead a team through a fast-paced environment with constant change and rapid growth.
Ability to make measured, objective, data-driven decisions on a daily basis.
Holds or will be expected to hold a Life & Health insurance license.

Responsibilities

Lead and empower a team of 10–15 licensed advisors and specialists through customer renewal cycles.
Coach and manage advisor performance through regular one-on-ones and monthly reviews, focusing on technical mastery, customer-centricity, and KPI achievement.
Meet customer retention targets by ensuring tailored, high-quality renewal and ongoing benefits experiences.
Use customer feedback and data to improve processes and deliver holistic, outcomes-focused advising.
Manage large-scale cross-functional initiatives that improve customer outcomes.
Lead change management for organization-wide improvements, helping advisors and managers adapt to change.
Build a culture of trust, feedback, engagement, and continuous learning rooted in Gusto’s values.
Partner with Product, Carrier Ops, Sales, and other customer experience teams to share advisor feedback and improve tooling, training, workflows, and customer experience.
Identify high-impact opportunities for AI, coach the team to build AI fluency, and use new tools to support smarter, more proactive customer engagement.
Balance customer impact and operational excellence while driving retention, expansion, and customer experience at scale.