Senior Vice President of Sales & Go-to-Market

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.

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.

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