Sales Development Representative

Outmarket AI; United States; On-site; USD 45,000 - 80,000; Full time

Job summary

Outmarket AI is seeking an assertive outbound SDR to build the pipeline from scratch, selling to commercial insurance agencies. You’ll craft multi-channel sequences, contact agency leaders, and drive discovery calls that fuel the Account Executive team.

Expect to innovate with AI-driven outreach and data-informed selling. You will operate in a fast-growing, startup environment, collaborating with marketing and leadership to sharpen targeting and messaging while expanding your outbound motion and

Qualifications

• 2+ years of outbound SDR or BDR experience selling technology or software to defined buyers.
• Background in commercial insurance or selling into insurance agencies preferred
• Genuinely phone-first with proven multi-channel prospecting across phone, email, and LinkedIn
• Track record of hitting and exceeding pipeline and meeting generation targets
• Strong research and writing skills with ability to personalize outreach rather than rely on volume
• Comfort in a fast-paced startup environment with a build-the-playbook mindset
• Fluency with CRM and modern sales engagement tools, plus appetite for AI-driven workflows

Responsibilities

• Build and execute outbound sequences across phone, email, and LinkedIn targeting commercial insurance agencies.
• Research target accounts to understand each agency’s book of business, growth priorities, and pain points, then craft personalized outreach.
• Leverage AI tooling to research, personalize, and prospect at scale, replacing manual steps with AI-powered workflows.
• Qualify prospects and book discovery calls for the Account Executive team, hitting monthly pipeline targets.
• Create and test outbound templates and talk tracks for the team to build on.
• Track all activity in the CRM and share market feedback with sales/marketing on resonance.
• Partner with marketing and sales leadership to sharpen targeting, messaging, and outbound motion.
• Share best practices and learn quickly in a collaborative, fast-moving team.

Skills

Outbound SDR

Phone prospecting

CRM proficiency

Research skills

Written communication

Time management

AI tooling

Tools

CRM software

LinkedIn

Email tools

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