Account Executive

FirmPilot; New York (NY); On-site; USD 140,000 - 150,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

Discretionary paid time off

Holidays: 11 + 2 floating

Job summary

FirmPilot, the AI marketing platform, is hiring an Account Executive in NYC to close SaaS deals with owner-operators in law, dental, and home services. You’ll own prospecting, discovery, demos, and closing, shaping how clients see ROI from our product and using AI to personalize outreach.

You’re a seasoned closer with 5+ years selling SaaS, comfortable with consultative discovery and a fast-paced, hands-on early-stage team. A strong network and bias for action help you win.

Qualifications

• 5+ years closing SaaS or AI-native software, preferably at Series A/B startup.
• Experience selling to SMB or local professional services (law, dental, HVAC, home services).
• Strong discovery and consultative selling abilities.
• Clear POV on AI-assisted selling and pipeline hygiene.
• Proficient with modern sales tools (HubSpot, Outreach, Gong, LinkedIn).

Responsibilities

• Own full cycle: prospect → discover → demo → close.
• Run discovery to reveal compelling ROI and consent to act.
• Diagnose business problems and map to outcomes with demos as a tool.
• Build trust with owner-operators; deliver fast follow-through.
• Move deals through a tight, fast cycle in a skeptical market.
• Leverage AI in outreach and prospecting, not gimmicks.
• Provide field intel to product/marketing to shape the roadmap.

Skills

SaaS sales

AI-native software

Discovery/challenge selling

Consultative selling

Sales to SMB/owner-ops

HubSpot/Outreach fluency

Ambition in early-stage

Tools

HubSpot

Outreach

Dialers

Gong

LinkedIn

Claude/ChatGPT

Job description

We're hiring an 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.

What you'll actually do

• 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.

What we're looking for

• 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.

Bonus points

• 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.

Why this seat is worth it

• Product that actually works. 180%+ case lift, real ROI, customers who renew because the math is the math.
• Wedge into a massive market. 425K law firms in the US, and we're expanding into dental, home services, and elective medical. Every quarter the TAM gets bigger, not smaller.
• A buyer no one else is serving well. Owner-operator SMBs have been ignored by enterprise SaaS and abused by agencies. We're the first credible alternative.
• Investors who matter. HubSpot Ventures and Thomson Reuters Ventures aren't passive checks.
• A seat at the table. You'll influence pricing, packaging, ICP, and the next product wedge. Early AEs here become sales leaders, GMs, or founders themselves.

Compensation

Pursuant to applicable pay transparency laws, the base salary range for this role is $140,000 to $150,000 base, with additional commission based on performance ($280k+ OTE).

In addition to base salary and commission, FirmPilot offers:

• 100% premium cost for employee: health, dental, and vision coverage
• Discretionary paid time off
• 11 holidays observed, and 2 floating holidays