The short version

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.

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

• 3–5 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 five days a week. 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 $130,000 to $150,000 base, with additional commission based on performance ($260k+ 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

About FirmPilot

FirmPilot is an AI-driven legal marketing technology company that helps law firms grow their client base through automated, data-driven outreach solutions. We are rapidly scaling to meet the increasing demand for our platform.

We are seeking a dynamic Account Executive with experience selling to small, mid-sized, and enterprise law firms. This role requires a confident, strategic sales professional who can effectively engage law firm decision-makers, conduct high-impact product demonstrations, and represent FirmPilot at industry conferences to attract new buyers.

Responsibilities

Sales Execution & Closing

• Own the full sales cycle from prospecting to close, working with law firms ranging from small practices to enterprise-level firms.
• Conduct compelling product demonstrations tailored to law firm decision-makers, clearly articulating how FirmPilot’s AI-powered solutions drive firm growth.
• Lead executive-level sales conversations with managing partners, firm administrators, and legal marketing teams.
• Develop and execute outbound sales strategies, leveraging tools such as HubSpot, Clay, LinkedIn Sales Navigator, and AI-driven automation to increase engagement and conversion rates.
• Utilize data-driven insights to optimize sales efforts, analyze performance, and refine messaging.
• Maintain and manage pipeline activity in HubSpot CRM, ensuring accurate forecasting and deal progression.

Market Expansion & Thought Leadership

• Speak at legal industry conferences, webinars, and networking events to establish credibility and generate new business opportunities.
• Work closely with the RevOps team to develop thought leadership content, case studies, and sales collateral that resonate with law firm buyers.
• Develop deep industry knowledge to educate law firms on legal marketing trends, AI-driven automation, and best practices for client acquisition.
• Build and maintain long-term relationships with key legal industry stakeholders, positioning FirmPilot as the go-to solution for law firm growth.

Collaboration & Sales Optimization

• Work cross-functionally with the BDR and RevOps teams to refine lead qualification and outreach strategies.
• Provide feedback on sales enablement materials, messaging, and positioning to ensure alignment with buyer needs.
• Stay ahead of legal technology and marketing trends to continuously adapt and improve the sales approach.

Qualifications

• Two to six years of B2B SaaS sales experience with a proven track record of selling to law firms, legal professionals, or professional services organizations.
• Experience closing deals with small to enterprise-level law firms, engaging directly with firm partners, legal administrators, and marketing teams.
• Strong ability to conduct high-impact product demonstrations, translating product features into clear, compelling value propositions.
• Confident public speaker, with experience presenting at industry conferences, hosting webinars, or leading sales-driven panel discussions.
• Proven ability to strategically nurture leads, negotiate contracts, and close high-value deals.
• Proficiency with CRM and sales automation tools (HubSpot, Salesforce, Clay, Outreach, SalesLoft).
• Excellent written and verbal communication skills, with the ability to engage and influence high-level decision-makers.
• Self-motivated and comfortable working in a fast-paced startup environment, adapting to shifting priorities and market conditions.

Why Join FirmPilot

• Be part of a high-growth, VC-backed startup transforming legal marketing with AI.
• Work with a highly skilled team of sales and marketing professionals in a collaborative, results-driven environment.
• Competitive compensation with uncapped earning potential.
• Remote-first work environment with flexibility.
• Career growth opportunities, including paths to Senior Account Executive, Enterprise Sales, and Sales Leadership roles.
• Access to cutting-edge sales technology, including HubSpot, Clay, and AI-driven automation tools.
• Travel stipend for attending legal conferences, networking events, and industry trade shows.
• Comprehensive health and dental benefits.

This role is ideal for a top-tier sales professional who can own the room during law firm demos, confidently speak at industry events, and drive high-value client acquisition across all firm sizes. If you thrive in a fast-paced, innovative environment and are ready to make an impact, we’d love to hear from you.

Compensation

Pursuant to applicable pay transparency laws, the base salary range for this role is $130,000 to $150,000 base, with additional commission based on performance ($260k+ 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

About FirmPilot

FirmPilot is the first AI-powered marketing platform purpose-built to replace traditional marketing agencies for law firms. Our patent-pending AI Legal Marketing Engine, trained on 5M+ pieces of legal marketing content and thousands of real cases, delivers SEO, PPC, Local SEO, Generative Engine Optimization, digital PR, social, and website optimization through a single platform with transparent, flat-fee pricing. The result: clients see 180%+ increases in case volume, 50–70% cost savings vs. agencies, and payback in 3–6 months. We retain 96% of our customers.

We closed an oversubscribed $22M Series A-1 in February 2026 (total funding: $27.25M) led by DeepWork Capital with participation from Thomson Reuters Ventures, HubSpot Ventures, Blumberg Capital, and Data Point Capital. We're ~40 people scaling to ~70 this year, and our thesis is expanding from legal into dental, HVAC, home services, and other professional-services verticals. The SVP of Sales & GTM will own that commercial expansion from day one.

The Role

This is the first dedicated executive sales hire at FirmPilot. You're inheriting a founder-led motion with strong product-market fit and real capital behind it, and your job is to turn it into a scalable, multi-segment revenue organization.

You will own the entire commercial engine: outbound pipeline generation, inbound conversion, AE performance, BDR development, deal strategy, forecasting, channel efficiency analysis, and the eventual buildout of a Customer Success function reporting into you. You'll sit shoulder-to-shoulder with the CEO on pricing, packaging, partnership activation, and the sequencing of our expansion beyond legal.

This is not a "hire a team and manage from dashboards" role. You will get on calls. You will close deals. You will rewrite the demo script when it's not landing. You will build the outbound sequences yourself before you ask a BDR to run them. You operate at 30,000 feet and in the weeds on the same day.

What You'll Own

Sales Organization Design & Execution

• Architect and scale a repeatable sales process across inbound and outbound motions, from first touch through closed-won
• Build, manage, and coach a team of AEs and BDRs, including ride-alongs on live calls, deal reviews, and pipeline inspections
• Develop and iterate on sales demo scripts, pitch decks, objection-handling frameworks, and competitive positioning materials
• Design and run BDR training programs covering call scripts, AI-personalized outbound sequences, cadence management, and qualification criteria
• Personally jump on sales calls to support AEs on high-value or complex deals, this is a player-coach role

Pipeline & Outbound Engine

• Build outbound sequences leveraging AI personalization at scale, you should have a point of view on how AI-assisted prospecting and selling changes the BDR/AE workflow
• Design call scripts and multi-channel cadences (phone, email, LinkedIn, direct mail) tailored to SMB professional services buyers who are skeptical of marketing vendors
• Own the outbound motion end-to-end: targeting, messaging, sequencing, testing, and iteration based on conversion data

Reporting, Forecasting & Channel Analysis

• Build and own BDR reporting (activity metrics, conversion rates, pipeline contribution) and AE reporting (pipeline coverage, stage velocity, win rates, average deal size)
• Deliver accurate weekly and monthly forecasts to the CEO and board, you understand bottoms-up forecasting and can defend your numbers
• Analyze the efficiency of every sales channel and marketing source by cost-per-lead, cost-per-opportunity, cost-per-closed-deal, and LTV, then use that analysis to reallocate spend and effort in partnership with Marketing

Deal Strategy & Nurturing

• Own deal nurturing workflows for prospects who aren't ready to buy today, build the drip sequences, re-engagement triggers, and follow-up systems that keep FirmPilot top-of-mind
• Develop a consultative selling approach that educates law firm owners on the shift from agency retainers to AI-powered marketing, our buyers need to be sold on the category, not just the product

GTM Strategy & Expansion

• Partner with the CEO on pricing and packaging evolution as FirmPilot ships deeper integrations (case management platforms, revenue attribution)
• Help sequence the expansion from legal into adjacent verticals (dental, HVAC, elective medical, home services), including ICP definition, messaging, channel strategy, and early sales plays
• Activate strategic investor relationships as real distribution channels, not just logos on a press release

What We're Looking For (Required)

• 8+ years in B2B sales leadership with at least 3 years at the VP or SVP level
• Experience scaling a SaaS or AI-native platform 
• Direct experience selling into SMB or local professional services - law firms (ie personal injury, family, criminal defense, etc), dental, HVAC, home services, elective medical, or similar. You understand the buyer: owner-operators who've been burned by agencies, don't have an in-house marketer, and need to see ROI fast
• Deep fluency in consultative selling - you can diagnose a prospect's business problems, map them to outcomes, and build trust with high-EQ conversations rather than feature dumps
• Proven track record building and scaling outbound sales teams (BDRs and AEs) from early-stage or founder-led motions into structured, metrics-driven organizations
• Hands-on comfort writing call scripts, building outbound sequences, designing demo flows, and coaching reps through live deals - not just reviewing dashboards
• Experience with AI-assisted sales tools and workflows - you have a perspective on how AI changes prospecting, personalization, and pipeline management
• Strong analytical chops: you can build a forecast model, run a cost-per-acquisition analysis across channels, and use data to make resourcing decisions
• Willingness to be in-office in NYC - this is not a remote role