Customer Success Representative

What You'll Do

• Respond to inbound calls and emails with timely, accurate, and professional service -- phones are the priority.
• Build strong relationships with agents and customers through clear communication and consistent follow-through.
• Gather information needed to complete or revise quotes and keep open quote files up to date.
• Resolve service and billing inquiries or route them to the right internal team when needed.
• Keep detailed, accurate notes in HubSpot (our CRM) after every interaction.
• Spot patterns in customer or agent feedback and escalate product or process insights to the team.
• Support internal operations like producer login setups and agent onboarding.
• Guide agents and customers on how to use our tools and self-service options.
• Contribute to building and refining the processes and playbooks that will define how this team operates for years to come.
• Take on new tasks as the business grows and needs shift.

Who Thrives Here

• You're comfortable with change. Processes evolve, priorities shift, and not everything is fully defined yet. You adapt without getting bogged down.
• You make informed calls with information. You handle ambiguity well -- you gather what you have, use good judgment, and move.
• You're curious about insurance. You don't need to be an expert on day one, but you want to understand how it works and get better at it over time.
• You're tech-forward and AI-curious. You pick up new tools quickly, you're not intimidated by systems, and you're genuinely interested in how AI is changing the way teams work.
• You manage your workload well. Whether you're on a call or working through emails, you stay on top of what needs attention and keep things moving.
• You work well in a small team. Everyone can see everyone's work here. You communicate openly, help when needed, and take ownership of your piece.

Basic Requirements

• 1+ years of experience in customer service, support, or an insurance-related role.
• Comfortable working in a fast-paced environment where tools and processes are still evolving.
• Strong problem-solving skills and the ability to manage multiple tasks at once.
• Experience with CRM tools -- HubSpot experience is a plus.
• Excellent written and verbal communication skills with strong attention to detail.
• Able to listen actively, empathize, and de-escalate professionally.
• Hybrid availability: Must be able to work from our downtown Chicago office Tuesday through Thursday.

Benefits

• Base Salary: $55,000
• ISO stock options
• Medical, dental, and vision coverage for you and your dependents
• HSA with company contributions
• 401(k) with company match
• Flexible time off
• 10 company-paid holidays
• Paid family leave
• Catered team lunch every Tuesday
• Monthly team events
• Free onsite gym membership