Mid-market account executive

Who We Are

Pibit.AI is an SF–based insurtech company reconstructing the art (and science) of commercial underwriting for carriers and MGAs. At the heart is the CURE™ platform, the industry’s only centralized underwriting risk environment fueled by agentic underwriting services that delivers decision-ready outcomes. It converts submissions into decisions by automating intake, triage, and data enrichment from documents and external sources while surfacing risk insights so you can win the right accounts faster, scale throughput, and reduce loss ratios.

Backed by Y Combinator, our proprietary platform serves dozens of clients across the U.S., enabling:

• 85% faster underwriting
• 32% increase in GWP per underwriter
• Up to 700 basis points improvement in loss ratios

What’s Expected From You (Besides Knowing How to Use a Calendar)

As our Mid-Market Account Executive, you’ll chase down clients with annual revenues between $10 million and $1 billion—companies big enough to have meetings about meetings, but small enough to still answer your emails.

At Pibit, your mission (and yes, you should choose to accept it) is to hunt down new logos in the U.S. insurance jungle: carriers, MGAs, and other acronym-loving entities.
No hand-holding, no babysitting—you’ll run the full sales cycle from “Hi, nice to e-meet you” to “Here’s the signed contract, let’s party.”

You’ll own everything: cold outreach, dazzling demos, stakeholder herding, contract negotiations, CRM updates (yes, you will update the CRM), and closing deals that make our CFO smile.
Your target? $450K in ARR.
Ambitious? So are we.

Bonus points if you speak fluent insurance lingo and don’t break into a cold sweat when someone says “underwriting workflows.”
Basically: sell smart, sell hard, and bring snacks for the ride.

You’ll Crush It In This Role If

• You’ve been around the SaaS block: 3–6 years of B2B sales experience, ideally mid-market.
• You’re a sales ninja: objection handling, solution design, complex negotiation—you’ve got the stories.
• You speak human: can explain technical stuff to non-technical folks (no “synergize the paradigm” talk).
• You don’t need babysitting: take initiative, follow up like a pro, and prospect proactively.
• You speak fluent HubSpot: CRM hygiene is your thing. Bonus if you’ve wrangled SalesNav, Lusha, DataNyze, Outreach, or ZoomInfo.
• You’re travel-ready: expect ~30 days/year in the U.S. for client meetings (and discovering what “biscuits and gravy” actually means).
• Insurance doesn’t scare you: you know what an MGA is. Bonus if you’ve dealt with underwriting or claims workflows.

Key Responsibilities

• Full Sales Cycle & Prospecting: Own the entire sales process for mid-market insurance accounts—from first outreach to contract signature.
• Solution Selling & Demos: Deliver tailored demos that make underwriters say, “Wait… you can do that?”
• Stakeholder Engagement: Build relationships with underwriting, claims, IT, and other key teams.
• Cross-Functional Collaboration: Partner with Sales Engineers, Product, and Customer Success to deliver wow-worthy proof-of-concepts.
• Pipeline & Forecast Management: Keep the CRM clean and forecast accurately to hit your $450K ARR target.
• Account Growth: Focus on new logos but spot upsell/cross-sell opportunities when they appear.

Why Join Pibit?

• Get in early—join a rocket ship still on the launchpad (and help build the rocket).
• Work shoulder-to-shoulder with the founding team.
• Solve real-world headaches (PDFs, emails, attachments) with an AI-native product that delivers.
• Zero corporate fluff: we care about impact, not titles (but Head of Making Magic Happen is up for grabs).
• Competitive compensation and a vertical career trajectory.
• Fast growth = fast promotions.
• Legendary offsites. Questionable memes. Unbeatable team.

Pibit is an equal opportunity employer.
We love brains of all kinds and are committed to building a diverse, inclusive crew.
Need accommodations during the hiring process? Just say the word.

‍