Account Executive

FirmPilot•New York, NY

12d•$130,000 - $150,000•Onsite

About The Position

We're hiring an early Account Executive to sell FirmPilot, the AI marketing platform replacing the agencies that have been overcharging and underdelivering for law firms (and soon, every other local services business worth winning). We just closed an oversubscribed $22M Series A-1 (Blumberg, Thomson Reuters Ventures, HubSpot Ventures). Our customers are seeing 180%+ more cases. The category is wide open. The product works. We need closers who can sit across from an owner-operator, diagnose what's actually broken, and earn the right to fix it. This is not a "hit the phones and pray" role. It's a consultative, high-EQ seat for an AE who already knows how to run discovery that bends a deal, not just check boxes in a CRM. Who you're selling to You already know this person. You've sold to them before. They're a managing partner at a personal injury firm, or a dentist who owns three practices, or an HVAC operator doing $8M who knows their phone should be ringing more. They've hired three marketing agencies in the last four years. Two ghosted them. One sent monthly PDFs full of "impressions." None of it generated cases, patients, or jobs. They don't have a CMO. They don't want one. They want to see leads, and they want to see ROI, and they're skeptical of anyone in a Patagonia vest promising "AI." If you understand that buyer in your bones, the trust deficit, the burned trust, the way they make decisions over text after their last consult of the day — you'll do well here.

Requirements

5+ years closing SaaS or AI-native software, ideally as an early AE at a Series A or B startup. You know what it's like when the playbook is half-written and you're writing the rest.
Direct experience selling to SMB or local professional services — law firms (PI, family, criminal defense, immigration), dental, HVAC, home services, elective medical, vet, or similar owner-operator-led businesses. You've sat across from these buyers and you know how they think.
Real consultative chops. You can run a discovery call that surfaces what the prospect won't say in the first ten minutes. You know how to use questions, not just ask them. You can tell the difference between a champion and a coach, and you know when a deal is dying before the prospect does.
A point of view on AI-assisted selling. Not "I've used ChatGPT once." A real take on how AI changes prospecting, personalization, and pipeline hygiene — and what it doesn't change.
Fluency with the modern stack. HubSpot, Outreach (or similar), dialers, Gong, LinkedIn, Claude/ChatGPT for research and outbound. You don't need training; you need to be unblocked.
Hunger for an early-stage seat. You want to be the 3rd or 4th AE, not the 30th. You like ambiguity. You don't need a manager to tell you what to do on a Wednesday afternoon.
You'll be in our NYC office, this is a build-the-thing-together role, not a Zoom role. If that's a dealbreaker, this isn't the one.

Nice To Haves

You've sold marketing software, ad tech, or anything where the customer measures you in pipeline-to-revenue.
You have a network of law firm owners, dental group owners, or local services operators you can call tomorrow.
You've sold through agency replacement deals before — you know how to handle "I'm already paying someone $8K/month for this."
You've worked somewhere where the founder was still in the sales motion. You like that, not despise it.

Responsibilities

Own a full cycle: prospect → discover → demo → close. We'll feed you plenty of pipeline, but the best AEs here build their own.
Run discovery that finds the compelling reason to act — not surface pain. The difference between "marketing isn't working" and "I just signed a personal guarantee on a second office and I have 90 days to make it pencil" is the entire deal.
Diagnose business problems and map them to outcomes. Demos are a tool, not a crutch. If you're feature-dumping by minute six, you're losing.
Build trust with owner-operators who've been lied to before. That means hard truths, fast follow-through, and zero BS in writing.
Move deals through a tight cycle. Our ICP buys faster than enterprise but is more skeptical than mid-market — calibrate accordingly.
Use AI in your workflow the way our product uses it for customers: as leverage, not gimmick. Claude for personalization, Outreach for sequencing, HubSpot as truth, dialers when warranted, and a real point of view on what's worth automating vs. what only works human-to-human.
Give product and marketing the field intel they need. Early AEs here aren't just selling, they're shaping what we build and how we position it.