Senior Account Executive

Outmarket AI Inc.; Friendly (MD); Remote; USD 100,000 - 150,000; Full time

Benefits offered by this job

Competitive salary

Uncapped commission

Equity in a fast-growing company

Full health, dental, and vision benefits

Remote-first with flexible hours

Job summary

A fast-growing AI company in the United States is seeking a Senior Account Executive to own the full sales cycle for deals ranging from $25K to $250K ACV. This role emphasizes selling innovative solutions in a traditional industry, requiring candidates to create demand and have proven sales success. Competitive salary, uncapped commissions, and equity in a rapidly scaling company are offered, alongside a fully remote working environment. Interested candidates should apply with their resume and a compelling sales story.

Qualifications

• Proven quota attainment at or above 100%, demonstrating sales success.
• Experience in selling disruptive products where demand had to be created.
• Ability to manage multiple complex sales deals simultaneously.

Responsibilities

• Own the full sales cycle including discovery, negotiation, and closing.
• Generate insights about distribution performance to teach customers.
• Win new business as the primary motion and expand customer relationships.

Skills

Sales

Communication

Storytelling

Negotiation

Job description

Senior Account Executive

Help Redefine Insurance with AI

US (Remote Friendly)

GTM

About Outmarket

Outmarket is building the intelligence layer for commercial insurance. Our AI-powered platform helps brokers, MGAs, wholesalers, and carriers unlock value from their data and streamline complex distribution workflows. The insurance industry has operated the same way for decades — we're changing that, in a $1 trillion market that is dramatically underserved by modern technology.

Our co-founders bring rare depth: Vishal built GTM and product at Uber, Meta, and Ethos; Anshu led engineering at Meta and Ethos and was an early leader of the IBM Watson AI team. The broader team comes from Meta, Uber, Adobe, and IBM. We've already partnered with some of the most innovative agencies and MGAs in the industry — and we're scaling quickly.

Why This Role

• Solve for a category you help create – a challenger sell in a traditional industry ripe for disruption.
• Work with world‐class founders and a Head of Sales who are invested in your success and directly accessible.
• Work a rich demand mix: strong inbound momentum, referrals, investor introductions, and deep insurance association relationships.
• Meaningful equity, uncapped commission, and a clear path to grow as the company scales.

What You’ll Do

• Own the full sales cycle – discovery, business‑case development, negotiation, and close – on deals from $25K to $250K ACV and growing.
• Lead with insight: teach buyers something meaningful about their distribution performance before you ever pitch a product.
• Win new logos as the primary motion, and expand relationships as customers see results.
• Show up as a credible voice at industry conferences and through our insurance association partnerships.
• Feed market intelligence back to product and leadership to sharpen our ICP, messaging, and roadmap.

What We’re Looking For

The most important thing: you know how to sell something new. Our buyers didn’t wake up this morning with budget allocated for what we build. You’ll need to create conviction, build the business case, and drive urgency around change in a traditional industry. Beyond that:

• Proven quota attainment at or above 100% – with numbers on the resume, not just adjectives.
• Experience selling a disruptive product or new category where you had to manufacture demand, not just respond to it.
• Comfortable running multiple complex deals in parallel with rigor and velocity.
• Thrives in a fast‑moving, early‑stage environment – you build your own process and don’t wait for a playbook.
• Strong communication and storytelling – you sell on value and outcomes, not features.

Bonus If You Have

• Background in insurance, insure‑tech, or adjacent verticals (fintech, health‑tech, reg‑tech).
• Familiarity with how the distribution chain works – carriers, MGAs, brokers, wholesalers.
• Experience at a Seed, Series A, or Series B company where you helped shape GTM from early days.

What You’ll Get

• Competitive salary and uncapped commission.
• Meaningful equity in a fast‑growing company.
• Full health, dental, and vision benefits.
• Remote‑first with flexible hours.
• Direct access to founders, leadership, and executive buyers from day one.

Interested?

Send your resume or LinkedIn to [e-mail] with a short note on why you’re excited about this space and a deal or moment you’re proud of – ideally one where you had to create demand that didn’t previously exist.

We move quickly on strong candidates.