Customer Success Manager, Small & Medium Business - Remote

Overview

We’re looking for a nimble and entrepreneurial Customer Success Manager to support our growing base of SMB customers. In this role, you’ll manage a large, diverse portfolio of employer clients – delivering scalable, programmatic support across onboarding, renewals, and open enrollment.

In Short

• Manage a large book of SMB employer clients, providing programmatic support across onboarding, open enrollment, and renewal through scalable processes
• Coordinate and execute streamlined onboarding processes, primarily during peak season when most new companies go live
• Support open enrollment planning and execution through standardized toolkits, training sessions, and communication best practices, including collaboration with brokers
• Deliver timely and proactive outreach to customers regarding enrollment challenges or other issues to mitigate poor member experiences and customer escalations
• Track customer health, satisfaction, and enrollment metrics to identify risks and surface opportunity areas for greatest impact
• Advocate for customer needs internally, sharing feedback and insights to inform product roadmap and service improvements
• Partner with internal teams to resolve customer questions, triage escalations, and improve processes
• Contribute to the development of internal tooling and dashboards to generate visibility into portfolio and create automated workflows and communications for account cohorts
• Support Sales with customer references and develop a subset of SMB champions

Requirements

• 2-4 years of experience in Customer Success, Account Management, or Customer Support – ideally within health benefits, HR/benefits tech, or digital health
• Experience managing a high volume of customers and providing structured support at scale
• Strong organizational and time management skills – able to prioritize effectively across multiple accounts and deliverables
• Clear, empathetic communicator with a knack for distilling complex topics into actionable guidance
• Comfortable working cross-functionally and collaborating in a fast-paced, evolving environment
• Tech-savvy and data-minded – you’re comfortable navigating internal tools and using data insights to drive prioritization
• Customer-first mindset with a strong sense of accountability and follow-through
• A team player with a learning mindset – open to evolving processes and systems

Benefits

• Thrives in a startup environment
• Experience with healthcare, specifically with employer benefits or insurance, a plus