Sales Development Representative

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

• The opportunity to join early and help define the outbound motion with no legacy constraints

• Meaningful influence on how Outmarket builds pipeline, positions its product, and scales GTM

• A fast-learning environment where you’ll develop both modern outbound fundamentals and AI-native prospecting skills

• A clear path to grow as the company and team scale