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