Note: The job is a remote job and is open to candidates in USA. Outmarket AI is an AI platform purpose-built for commercial insurance agencies. The Sales Development Representative will build and execute the outbound sales engine, prospect and qualify commercial insurance agencies, generate pipeline, and collaborate with sales and marketing leadership to refine messaging and prospecting workflows.
Responsibilities
- 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
Skills
- 2+ years of outbound SDR or BDR experience, ideally selling a technology or software product into a defined buyer persona
- 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
- 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
- Background in commercial insurance, whether at an agency, carrier, wholesaler, or insurtech, or experience selling into insurance agencies is strongly preferred
- Direct experience prospecting into commercial insurance agencies, principals, owners, operators, or producers
Benefits
- Remote work arrangement
- 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
Company Overview