Customer Success Representative

Honeycomb Insurance; Chicago (IL); Hybrid; USD 50,000 - 65,000; Full time

Benefits offered by this job

Hybrid work model

401(k) with company match

Medical, dental, and vision coverage

HSA with company contributions

Flexible time off

10 company-paid holidays

Paid family leave

Catered team lunch every Tuesday

Monthly team events

Free onsite gym membership

ISO stock options

Job summary

Honeycomb in Chicago is seeking a Customer Success Representative to be the first point of contact for agents and policyholders, handling calls, email and chat with a phone-first approach.

You’ll build relationships, manage quotes, resolve billing inquiries, document interactions in HubSpot, and help shape the CSR playbooks as the team scales in a fast‑growing insurance tech company.

Qualifications

• 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.
• Ability to listen actively, empathize, and de-escalate professionally.
• Hybrid availability: Must be able to work from our downtown Chicago office Tuesday through Thursday.

Responsibilities

• Answer questions and resolve issues via phone, email and chat.
• Manage call, email and chat queues with strong organization.
• Document interactions in HubSpot after every contact.
• Help shape processes and playbooks for the CSR team.
• Assist with agent onboarding and login setups.
• Guide agents and customers on using tools and self-service options.
• Identify patterns in feedback to improve service.
• Support billing inquiries and route as needed.

Skills

Customer service

Problem solving

Communication skills

Empathy

Time management

Tools

HubSpot

Job description

At Honeycomb, we're not just building technology; we’re reshaping the future of insurance.

Honeycomb is a rapidly growing global startup, generously backed by top-tier investors and powered by an exceptional team of thinkers, builders, and problem-solvers. Dual-headquartered in Chicago and Tel Aviv (R&D center), and with 6 offices across the U.S., we are reinventing the commercial real estate insurance industry, an industry long overdue for disruption. Just as importantly, we ensure every employee feels deeply connected to our mission and one another.

With over $100B in insured assets, Honeycomb operates across 23 states, covering more than 65% of the U.S. population and increasing its coverage.

If you’re looking for a place where innovation is celebrated, culture actually means something, and smart people challenge you to be better every day - Honeycomb might be exactly what you’ve been looking for.

What You'll Do

As a Customer Success Representative (CSR), you'll be the first point of contact for our agents and policyholders -- answering questions, resolving issues, and delivering a consistently positive experience across phone, email and chat. This is a phone-first role where you'll manage both call, email and chat queues throughout the day, so staying organized and on top of multiple channels is key.

But this isn't just a support role -- it's a chance to be part of something being built in real time. Our CS team sits at the center of everything at Honeycomb, and the people in these seats today have a real opportunity to shape how we work, influence the processes we put in place, and leave a lasting mark on a company that has built a strong foundation and is now accelerating.

• 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 ...
• 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

Honeycomb is growing fast, and still writing parts of the playbook. If you've ever wanted to work somewhere where your ideas actually get heard and your fingerprints end up on how a company operates -- this is that place. The people who do best here tend to share a few things in common:

• 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.
• Ability to listen actively, empathize, and de-escalate professionally.
• Hybrid availability: Must be able to work from our downtown Chicago office Tuesday through Thursday.
• 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

Honeycomb is committed to fair and equitable compensation practices. The base salary listed represents our good faith estimate for this role. Actual compensation may vary based on skills, experience, education, location, and market factors.