[Remote] Senior Leader, Benefits Advising

Note: The job is a remote job and is open to candidates in USA. Gusto is on a mission to grow the small business economy by handling payroll, health insurance, and HR. The Senior Leader, Benefits Advising will empower the advising renewal organization, focusing on customer retention, operational excellence, and integrating AI into the advising experience. Responsibilities • 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 Skills • 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 Benefits • Health insurance • 401(k)s Company Overview • Gusto is an HR and payroll platform that simplifies complex tasks, empowering businesses to focus on what matters most. It was founded in 2011, and is headquartered in San Francisco, California, USA, with a workforce of 1001-5000 employees. Its website is Apply tot his job