[Hiring] Sales Development Representative @Outmarket AI

Role Description

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.

Qualifications

• 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.

Requirements

• 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.

Benefits

• 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.