Benefits Advising Manager

Responsibilities

• Provide regular coaching and performance management (via 1:1s and monthly reviews) focused on technical mastery, customer-centricity, and hitting KPIs.
• Deliver on retention targets by ensuring tailored, high-quality renewal experiences through a customer’s renewal and ongoing benefits experience.
• Use customer feedback and data to identify and drive improved processes and deliver more holistic, outcomes-focused advising. Act as project manager for large-scale, cross-functional initiatives that result in better outcomes for our customers.
• Guide organization-wide improvements, enabling advisors and managers to adapt and thrive in a dynamic environment.
• Build a culture rooted in Gusto’s values, creating an environment of trust, feedback, and continuous learning.
• Partner with Product, Carrier Ops, Sales, and other CX teams to act as the voice of the Advisor by surfacing feedback to improve tooling, training, workflows, and the overall customer experience.
• Identify high-impact opportunities, coach your team to build critical AI fluency, and shape the future of our customer journey by leveraging new tools for smarter, more proactive customer engagement.

Requirements

• 4-6 years of formal leadership experience in benefits advisory, customer success or renewals, or a similar field.
• Direct experience with small group health insurance (fully insured, level-funded or PEO models).
• Proven ability to drive revenue growth, customer retention, and expansion through consultative renewal and upsell strategies.
• Analytic and strategic thinker with the ability to translate data into insights and actions.
• Strong operational skills, proactive approach to process improvement, and previous 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 innovation with risk management, compliance requirements, and maintaining customer trust in a licensed advisory context.
• Experience with technology/automation solutions such as Salesforce, APIs, and benefits administration platforms.
• Executive presence with the ability to align leaders across CX, Sales, and Product, to lead high-impact initiatives.
• Customer-first mentality with a first-principles-thinking approach.
• Thrives in and can lead a team through a fast-paced environment with constant change and rapid growth.
• Able to make measured, objective, data-driven decisions on a daily basis.
• Holds (or will be expected to hold) a Life & Health insurance license.

Nice-to-Haves

• Experience managing OKR/team initiatives while leading a high performing team.

Compensation

• Cash compensation: $86,530 - $106,000 yearly in Phoenix and $92,245 - $113,000 yearly in Denver, Chicago and Las Vegas.
• All full-time employees receive competitive base pay, benefits, and equity (RSUs).