ABOUT OUTMARKET

Outmarket AI is an AI platform purpose-built for commercial insurance agencies. We help agencies grow revenue and reduce E&O risk without adding headcount, amplifying what their best people do in every customer engagement, across every workflow, and at every level of the organization.

We’re in hyper-growth mode. Not the traditional SaaS kind, where you scale revenue by scaling headcount in lockstep, but the AI-era kind, where the growth curve is exponential and the operating model is fundamentally different. Our customers are commercial insurance agencies learning to compete and win at a new scale using AI. We build that same model internally, and we prove it every day.

WHY THIS ROLE

Build the outbound engine from the ground up at a company defining a new category in commercial insurance
Shape the sequences, messaging, and prospecting motions that will influence how Outmarket sells for years to come
See your field work directly inform product direction and market narrative
Get a front-row seat to hyper-growth in the AI era, with clear room to grow alongside the team

WHAT YOU'LL DO

Build and execute outbound sequences across phone, email, and LinkedIn, targeting commercial insurance agencies that fit our ideal customer profile
Research target accounts to understand each agency’s book of business, growth priorities, and pain points, then craft relevant, personalized outreach that resonates
Leverage AI tooling to research, personalize, and prospect at scale, continuously replacing manual steps with AI-powered workflows
Qualify prospects and book discovery calls for the Account Executive team, hitting and exceeding monthly pipeline generation targets
Create and test outbound email templates and talk tracks for yourself and the broader team to build on
Track all activity in the CRM and share real-time market feedback with sales and marketing leadership on what is resonating and what is not
Partner closely with marketing and sales leadership to sharpen targeting, messaging, and the overall outbound motion
Share best practices and learn quickly in a collaborative, fast-moving team

WHAT WE'RE LOOKING FOR

The most important thing: you know how to create opportunity from scratch. This is not a passive pipeline role. You’ll need to earn attention from busy agency leaders, open real conversations, and consistently convert outbound effort into qualified pipeline. Beyond that:

2+ years of outbound SDR or BDR experience, ideally selling a technology or software product into a defined buyer persona
Background in commercial insurance, whether at an agency, carrier, wholesaler, or insurtech, or experience selling into insurance agencies is strongly preferred
Genuinely phone-first, comfortable and effective cold calling, with proven multi-channel prospecting across phone, email, and LinkedIn
A track record of hitting and exceeding pipeline and meeting generation targets
Strong research and writing skills, with the discipline to personalize outreach rather than rely on volume alone
Comfort operating in a fast-paced, resource-constrained startup environment where the playbook is still being built
Strong problem-solving, prioritization, and attention to detail in a deadline-driven setting
Fluency with CRM and modern sales engagement tooling, plus an appetite for adopting AI to work smarter

BONUS IF YOU HAVE

Direct experience prospecting into commercial insurance agencies, principals, owners, operators, or producers
Familiarity with the P&C commercial lines landscape and how agencies operate, grow, and manage E&O risk
Hands-on experience using AI tools to accelerate research, personalization, and outreach
Early-stage or founding GTM experience where you helped build the outbound motion, not just execute it

WHAT YOU'LL GET