Experienced Customer Success Manager – Small & Medium Business (SMB) Growth & Development

At arenaflex, we're revolutionizing the way small and medium-sized businesses navigate the complexities of health benefits and HR technology. As a nimble and entrepreneurial Customer Success Manager, you'll play a pivotal role in supporting our growing base of SMB customers, delivering scalable, programmatic support across onboarding, renewals, and open enrollment. If you're organized, resourceful, and excited to help small and midsize employers navigate arenaflex and ICHRA with confidence, this role is for you.

About arenaflex

arenaflex is a leading provider of innovative HR and benefits solutions, empowering small and medium-sized businesses to thrive in a rapidly changing landscape. Our cutting-edge platform, combined with our commitment to exceptional customer service, has made us a trusted partner for employers nationwide. As a Customer Success Manager at arenaflex, you'll be part of a dynamic team that's passionate about helping businesses succeed.

Key Responsibilities

As a Customer Success Manager, you'll be responsible for managing a large book of SMB employer clients, providing programmatic support across onboarding, open enrollment, and renewal through scalable processes. Your key responsibilities will include:

• Managing a diverse portfolio of employer clients, delivering timely and proactive outreach to customers regarding enrollment challenges or other issues to mitigate poor member experiences and customer escalations
• Coordinating and executing streamlined onboarding processes, primarily during peak season when most new companies go live
• Supporting open enrollment planning and execution through standardized toolkits, training sessions, and communication best practices, including collaboration with brokers
• Tracking customer health, satisfaction, and enrollment metrics to identify risks and surface opportunity areas for greatest impact
• Advocating for customer needs internally, sharing feedback and insights to inform product roadmap and service improvements
• Partnering with internal teams to resolve customer questions, triage escalations, and improve processes
• Contributing to the development of internal tooling and dashboards to generate visibility into portfolio and create automated workflows and communications for account cohorts
• Supporting Sales with customer references and developing a subset of SMB champions

Background We're Looking For

To succeed in this role, you'll need:

• 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 communication skills 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

Experience We'd Be Particularly Excited About

* Thriving in a startup environment

• Experience with healthcare, specifically with employer benefits or insurance, a plus

What to Expect

We interview rigorously based on integrity, talent, and drive; the trust we display in our teammates from day 1 is a reflection of the confidence we have in this process. We aim to evaluate the things you'll be doing every day as best we can, and we move quickly. Here's what to expect:

• 20-30 minute Zoom meeting to talk through your background and interest in arenaflex
• 30 minute Zoom meeting with the hiring manager to dive deeper into your experience and the role
• 30 minute Zoom meeting to meet 3-4 members of the team
• 30 minute Zoom meeting with the hiring manager to work through a live case study
• 30 minute Zoom meeting with our founders to discuss your approach to culture and our operating principles

Estimated Compensation Range

$103,000 - $160,000 USD

Why Join arenaflex?

At arenaflex, we're passionate about creating a workplace that's inclusive, supportive, and empowering.

We offer

• Competitive compensation and benefits package
• Opportunities for professional growth and development
• Collaborative and dynamic work environment
• Recognition and rewards for outstanding performance
• Flexible work arrangements and work-life balance
• Access to cutting-edge technology and tools
• A culture that values diversity, equity, and inclusion

How to Apply

If you're a motivated and customer-focused professional looking to make a meaningful impact, we encourage you to apply for this exciting opportunity. Please submit your resume and a cover letter outlining your experience, skills, and qualifications for the role. We can't wait to hear from you! Apply for this job