Senior Leader, Benefits Advising

About the Role:

The Senior Leader, Benefits Advising will empower 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 building mechanisms that drive customer retention, expansion, and exceptional customer experience at scale. This role will be at the forefront of helping integrate AI and automation into the advising experience, ensuring our teams leverage technology responsibly while maintaining the human touch that builds trust with small business owners.

About the Team:

Your team will support small business owners in accessing the best health insurance and holistic benefits offerings - including ancillary coverage, tax-advantaged accounts, and retirement plans like 401(k). Much of this work is centered around small group health insurance, including fully insured and level-funded plans, where tailored guidance is essential for customer success.

You'll directly empower a team of 4-6 frontline leaders and a total organization of 30-50 licensed advisors and specialists, guiding them through renewal cycles and enabling them to serve as trusted advisors to our customers.

Here's what you'll do day-to-day:

• Directly oversee and develop leaders: Coach and empower 4-6 leaders and their teams of licensed advisors.

• Lead CX strategic direction: Define and execute the renewal and advising strategy for Gusto's benefits customers.

• Drive retention and revenue growth:

• Deliver on retention targets by ensuring tailored, high-quality renewal experiences.

• Build playbooks to expand coverage across ancillary, tax-advantaged, and retirement offerings.

• Partner with Finance and CX leadership to establish and achieve revenue goals tied to renewals.

• Redesign advisor workflows to integrate AI and automation tools (e.g., Salesforce, Next Best Action, AI-powered recommendations), enabling advisors to spend more time on high-value customer engagement while ensuring responsible AI practices and human-in-the-loop oversight for critical decisions

• Champion compliance, ethics, and trust, ensuring all advisor recommendations meet regulatory standards while maintaining customer-first outcomes."

• Foster culture and engagement: Build a culture rooted in Gusto's values, creating an environment of trust, feedback, and continuous learning.

• Lead change management: Guide organization-wide improvements, enabling advisors and managers to adapt and thrive in a dynamic environment.

• Evolve the customer experience: Use customer feedback and data to refine renewal processes and deliver more holistic, outcomes-focused advising.

Here's what we're looking for:

• 5+ years of leadership experience in customer success, account management, or benefits/insurance advisory, including leading leaders.
• Proven ability to drive revenue growth, customer retention, and expansion through consultative renewal and upsell strategies.
• Direct experience with small group health insurance (fully insured and level-funded models) is required.
• Background in building scalable processes and mechanisms to support customer outcomes.
• 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, and communicate a compelling vision to both frontline teams and senior stakeholders.
• Customer-first mentality with a first-principles-thinking approach.
• Thrives in a fast-paced environment with constant change and rapid growth.
• Able to make measured, objective, data-driven decisions on a daily basis.

Our cash compensation amount for this role is $119,000/yearly to $154,000/yearly in Denver, Las Vegas, Chicago, Phoenix. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.