Sales Development Representative

Outmarket; Northern (KY); Hybrid; USD 65,000 - 90,000; Full time

Job summary

Outmarket is seeking an energetic Outbound SDR to build the initial demand engine for our AI platform in the commercial insurance space. You will craft multi-channel outreach, research target accounts, and leverage AI to personalize communications at scale.

You will qualify prospects and hand off qualified pipeline to the Account Executive team, collaborating with marketing to refine targeting and messaging as we scale.

Qualifications

• 2+ years in outbound SDR/BDR selling software to defined buyers.
• Experience selling into commercial insurance is preferred.
• Proven phone-first approach with multi-channel outreach.
• Proven track record of meeting or exceeding pipeline targets.
• Strong research and persuasive writing for personalized outreach.

Responsibilities

• Build and execute outbound sequences via phone, email, and LinkedIn.
• Research target accounts to tailor outreach to each agency.
• Leverage AI tools to accelerate research and personalization.
• Qualify prospects and book discovery calls for the Account Executive team.
• Create and test outbound templates and talk tracks for the team.

Skills

Outbound SDR

BDR experience

Phone outreach

Multi-channel prospecting

CRM proficiency

AI in sales

Research & writing

Pipeline generation

LinkedIn outreach

Tools

LinkedIn

CRM

Job description

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