ABOUT OUTMARKET

Outmarket is an AI-powered platform purpose-built for commercial insurance agencies. We help brokers, MGAs, and carriers extract insights, automate workflows, and move faster by turning unstructured data into action.

ABOUT THE ROLE

We are hiring an Insurance Operations Specialist to help our clients get real, practical value from the platform in the context of how their agencies actually operate.

This is a client-facing role for someone who already understands how insurance agencies and brokerages work. You will learn each client’s workflows, where their teams lose time, what creates friction, and what prevents adoption. Then you will help solve those problems through workflow redesign, training, enablement, issue triage, and day-to-day operational partnership.

You will act as an extension of your client’s operations team from our side of the table. You are being hired for your insurance domain knowledge and your ability to help teams work better. We will teach you the product.

This is an associate-level role with a direct path to Client Success Manager. You will partner closely with a CSM on a portfolio of accounts, own adoption and enablement work within those accounts, and take on more direct ownership over time as you are ready.

WHY THIS ROLE

• Work directly with insurance agencies and brokerages to improve how they operate day to day.

• Use your knowledge of agency workflows to drive real adoption and measurable client outcomes.

• Help shape the training materials, playbooks, and enablement systems that will support future growth.

• Partner closely with Client Success while building toward your own book of business.

• Join an early-stage company where the playbook is still being written and your impact will be visible immediately.

WHAT YOU’LL DO

• Own usage and adoption outcomes for a portfolio of agency and brokerage clients.

• Learn how each client operates across submissions, certificates, endorsements, renewals, servicing workflows, and internal handoffs.

• Identify where adoption has stalled, whether because a team is not logging in, a workflow has reverted to an old process, or the value is not landing with the right users.

• Diagnose root causes and design the right intervention, including retraining, workflow redesign, champion development, or improved internal communication.

• Deliver training sessions for audiences ranging from small service teams to large brokerage rollouts.

• Build enablement materials such as quick-reference guides, onboarding checklists, role-specific training paths, and adoption playbooks.

• Turn what works for one client into repeatable resources the broader team can reuse.

• Reproduce, document, and triage technical issues before escalating, then stay on them through resolution.

• Partner with your CSM on onboarding, business reviews, renewals, and expansion conversations.

• Keep account records, meeting notes, and follow-ups current and accurate.

WHAT WE’RE LOOKING FOR

• 3+ years of experience in an insurance agency, brokerage, or carrier environment across account management, client service, operations, underwriting support, claims, or similar roles.

• Strong working knowledge of how agencies actually run, including submissions, certificates, endorsements, renewals, and the systems that support them.

• Familiarity with platforms such as AMS360, Applied Epic, HawkSoft, Nexsure, or similar agency management systems.

• Demonstrated ability to change how people work, whether by rolling out a new process, improving adoption of a tool, or rebuilding a broken workflow.

• Strong written and verbal communication skills, including comfort working with senior stakeholders.

• Strong judgment and comfort operating in ambiguity without waiting for perfect information.

• A proactive mindset and willingness to identify problems before clients explicitly ask for help.

BONUS IF YOU HAVE

• A P&C license and/or designations such as CISR, CIC, CPCU, or similar.

• Experience training, teaching, or facilitating enablement in either a formal or informal capacity.

• Exposure to employee benefits in addition to commercial lines.

• Experience working in fast-moving startup or high-change environments.

WHAT YOU’LL GET

• A direct path to growth into a Client Success Manager role.

• The opportunity to help build the adoption, training, and enablement foundation for a growing client success organization.

• Meaningful ownership and visibility across client outcomes and internal operations.

• Close partnership with experienced client-facing teammates and cross-functional exposure across the company.

• The chance to bring deep insurance knowledge into a modern, AI-first platform built specifically for the industry.

WHAT THIS ROLE ISN’T

We would rather be direct about this up front.

This is an early-stage company. The pace is fast, priorities shift, and the work is not built around a predictable nine to five rhythm. There is no finished training curriculum waiting for you. You will help build it. No one will hand you a fully defined checklist every morning. You will be expected to look at your accounts, identify what needs attention, and move.

If you are coming from agency-side service work, the biggest adjustment is usually not the technology. It is the shift from reactive work to proactive work. Clients will not always tell you exactly what they need. Part of the job is figuring that out before they ask.

This is not a role for someone who wants tightly defined lanes, a highly scripted playbook, or a steady stream of inbound requests to manage. It is a role for someone who finds energy in ownership, problem-solving, and helping clients work better in ways that are often not obvious at first.