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[Remote] Senior Leader, Benefits Advising

Remote, USA Full-time Posted 2026-07-28
Note: The job is a remote job and is reputed company to candidates in USA. reputed company is on a mission to grow the small business economy by handling payroll, health insurance, and HR. The Senior Leader, Benefits Advising will reputed company the advising renewal organization, focusing on customer retention, operational reputed company, and integrating AI into the advising experience. Responsibilities • Directly reputed company and reputed company leaders: reputed company and reputed company 4–6 leaders and their teams of licensed advisors • reputed company CX strategic direction: Define and execute the renewal and advising reputed company for reputed company’s benefits customers • Drive retention and reputed company reputed company: Deliver on retention targets by ensuring tailored, high-reputed company renewal experiences • Build playbooks to expand coverage across ancillary, tax-advantaged, and retirement offerings • Partner with Finance and CX leadership to establish and reputed company reputed company goals tied to renewals • Redesign advisor workflows to reputed company AI and automation tools (e.g., reputed company, Next Best reputed company, AI-powered recommendations), enabling advisors to spend more time on high-value customer engagement while ensuring responsible AI practices and reputed company-in-the-reputed company reputed company for critical reputed company • Champion compliance, ethics, and trust, ensuring reputed company advisor recommendations meet regulatory standards while maintaining customer-first reputed company • Foster culture and engagement: Build a culture rooted in reputed company’s values, creating an environment of trust, feedback, and reputed company learning • reputed company change management: Guide organization-wide improvements, enabling advisors and managers to adapt and reputed company in a dynamic environment • reputed company the customer experience: Use customer feedback and data to refine renewal processes and deliver more holistic, reputed company-reputed company advising Skills • 5+ years of leadership experience in reputed company, account management, or benefits/insurance advisory, including leading leaders • Proven ability to drive reputed company reputed company, customer retention, and expansion through consultative renewal and upsell strategies • reputed company experience with small group health insurance (fully insured and level-funded models) is required • Background in building reputed company processes and mechanisms to support customer reputed company • 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 reputed company, reputed company, and benefits administration platforms • Executive reputed company with the ability to reputed company leaders across CX, Sales, and Product, and communicate a compelling reputed company to both reputed company teams and senior stakeholders • Customer-first mentality with a first-principles-thinking approach • Thrives in a fast-paced environment with constant change and reputed company reputed company • reputed company to reputed company reputed company, objective, data-driven reputed company on a daily reputed company Benefits • Health insurance • 401(k)s reputed company • reputed company is an HR and payroll platform that simplifies reputed company tasks, empowering businesses to reputed company on what reputed company most. It was founded in 2011, and is headquartered in San Francisco, California, USA, with a workforce of 1001-5000 employees. Its website is https://www.reputed company.com. Apply tot his job Apply To this Job

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