--- title: 'Head of Sales Enablement at Wordsmith AI' canonical: 'https://feeny.ai/job/head-of-sales-enablement-wordsmith-ai-new-york-efap6c2jkmkg' type: 'job' last_seen: '2026-09-04' --- # Head of Sales Enablement at Wordsmith AI - **Company:** Wordsmith AI - **Location:** New York, NY - **Employment:** full-time - **Work type:** onsite - **Posted:** 2026-08-03 - **Last confirmed live:** 2026-09-04 - **Apply:** https://jobs.ashbyhq.com/wordsmith/4a6d8627-23fd-42fb-8e1c-e2b0f0d197cc ## Job description ## HEAD OF SALES ENABLEMENT - NYC New York Wordsmith Wordsmith is building the legal operations platform for in-house teams, and we are growing fast. We believe in-house legal is becoming one of the most important functions in the AI era. Every business is moving faster, but legal work is still too often scattered across inboxes, chats, documents, and disconnected systems. Wordsmith brings that work into one system. Requests come in from across the business, AI agents handle the routine, lawyers stay in control where judgment matters, and every step is captured as work happens. We are built for in-house legal, not law firms. Our goal is to help legal teams move faster, reduce unnecessary external counsel spend, and become a function the business can run with. More than 500 companies, including Financial Times, Safelite, Trip.com, Canva, Starling, and Sage, use Wordsmith. Backed by $100M from Index Ventures, General Catalyst, Highland Europe, and others, we are building one of the defining companies in legal AI. ## The Role We’re hiring a Head of Sales Enablement to build and lead our global enablement function from the ground up. This is a rare opportunity to shape a critical function at an important stage of growth. As our first enablement leader, you’ll set the strategy, build the programs, and create the infrastructure that helps our revenue organisation perform at a higher level as we scale. You’ll work closely with Pre-Sales Legal Engineering, Product Marketing, Product, Engineering, and Revenue Leadership, but you’ll own the enablement vision and execution. This is not a traditional methodology-first enablement role. We’re looking for a product-oriented leader who can help our AEs build real credibility with General Counsel, Chief Legal Officers, Legal Ops, and other sophisticated buyers. You’ll help the team stay sharp on product, confident in demos and trials, and ready to keep pace with a platform that evolves quickly. ## What you’ll do - Build and lead the global sales enablement function, creating the strategy, programs, and operating rhythm that help the revenue team perform at a high level - Design onboarding, ramp, and certification programs for AEs across Enterprise, Mid-Market, and SMB, with clear milestones and measurable outcomes - Act as the bridge between Product, Engineering, and Sales, turning new product releases into practical guidance that helps sellers stay credible and effective with buyers - Raise the quality of demos, trials, and competitive conversations by building the right playbooks, coaching, and content in partnership with Pre-Sales Legal Engineering and Product Marketing - Establish a scalable coaching infrastructure, track the metrics that matter, and coach and grow the enablement team over time ## What we’re looking for - Experience building a sales enablement function or program from scratch in a fast-growing company, with a strong track record of creating practical, high-impact programs - Experience managing and developing enablement talent, alongside the ability to operate as a hands-on player-coach when needed - Strong product instincts, confidence running polished and outcome-oriented demos, and the ability to help sellers build credibility with sophisticated buyers - A data-informed, highly collaborative approach, with the judgment to work effectively across Product, Engineering, Marketing, and Sales - Clear communication, high ownership, and a bias toward action in fast-moving environments ## How we work We’re an in-office team in New York. We work together because it makes us faster, sharper, and more effective. You should expect to be in the office as your default. This is a high performance environment. We set a high bar, move quickly, and expect people to take ownership of real problems. There isn’t always a clear path. The people who do well here figure things out, stay close to the work, and keep pushing until they get to the right outcome. This role requires patience, structure, and strong judgement. You’ll be trusted to run complex deals with a high degree of autonomy. ## Why Wordsmith We’re in a period of strong momentum — growing quickly, winning new customers, and expanding into larger accounts. The product is landing well, the market is ready, and the team is scaling to meet demand. If you want to be in the room, close meaningful deals, and grow quickly in a high bar environment, this is one of the best places to do it. ## About Wordsmith AI ## Company Overview - **One-liner**: Wordsmith provides an AI-native legal operations platform that captures, triages, resolves, and records every legal request from the business, enabling in-house legal teams to work at the speed of AI. - **Entity Type**: Private (Series B) - **Headquarters**: London, England, United Kingdom - **Founded**: 2023 - **Founders**: Ross McNairn (CEO), Volodymyr Giginiak (CTO), Robbie Falkenthal (COO) ## Core Business - **Primary industry/industries**: Legal Technology (LegalTech), Enterprise AI, Workflow Automation - **Target customers**: In-house legal departments at mid-to-large enterprises across all industries (B2B, Enterprise) - **Mission or purpose statement**: To be the Northstar for legal intelligence in business — to bring the legal function in-house by making it measurable, compressible, and owned, just as every other major corporate cost centre has been. ## Products & Services - **The Wordsmith Platform (Legal Operations System)**: An end-to-end AI-native system built around four core workflows: **Receive** (captures legal requests from Slack, email, Salesforce, Teams, and procurement systems), **Route** (assigns ownership, priority, and context), **Resolve** (automates routine legal work using AI agents — drafting, redlining, research, translation — while escalating complex decisions to lawyers), and **Record** (logs every decision, action, and rationale in real time for audit-ready governance). - **Contract Review & Workflow Integration**: End-to-end contract review embedded directly into business tools like Slack, Gmail, and procurement systems. Reviews are collaborative and web-native. - **Word Integration**: A plugin allowing lawyers to review, redline, draft, research, and translate without leaving Microsoft Word. - **AI Agents**: Chain drafting into a full end-to-end workflow — receive the request, draft the document, route for approval, and send — with no manual step required. - **Global Legal Intelligence Engine**: Covers hundreds of trusted sources across 130+ jurisdictions, combined with deep knowledge of the customer’s own entities, risk profile, and prior positions. ## Market Standing - **Valuation/Market Cap**: Not publicly disclosed (private company) - **Key Metric**: Total funding raised — **$100M** across two rounds. Last round: **€60.2M ($70M) Series B** (announced June 2026). - **Notable Investors/Partners**: Index Ventures, Highland Europe, General Catalyst (the firms behind Figma, Stripe, Discord, Airbnb, Revolut, and Canva). - **Growth Signals**: - Used by **500+ organisations globally**, including major enterprises such as **BT, Financial Times, Safelite, Trip.com, and Canva**. - Reports that **Trustpilot cut contract review time by 85%** using the platform. - Planning to grow workforce from ~100 to **~300 employees**, with significant **US market expansion**. - Founded in 2023 and achieved this scale in just over two years. ## Competitive Advantages - **Category-defining position**: Wordsmith is not a legal copilot for individual lawyers — it is an **operating system for the entire in-house legal function**, managing complete request flows across the organisation. This system-level approach is a structural shift away from traditional point-tools. - **Conflict-free business model**: Wordsmith sits on the side of the *buyer* of legal services (the in-house team), not the *seller* (law firms). All other legacy tools were built to serve law firms. Wordsmith’s incentives are aligned with removing friction and cost for the enterprise. - **Vertical-first AI strategy**: Deeply specialised in legal workflows rather than a generalist AI platform, making the product deeply relevant and defensible in a $1.1T global legal market. - **Founding team**: Led by a CEO (Ross McNairn), CTO (Volodymyr Giginiak), and COO (Robbie Falkenthal) who blend legal domain expertise with deep AI and engineering capability. ## Strategic Focus - **Scale globally, with a US expansion priority**: The Series B is explicitly earmarked to accelerate growth in the US market. - **Hire exceptional talent**: Grow the team to ~300 people, maintaining a “fewer, better people” philosophy — a small group of brilliant specialists rather than a crowd of generalists. - **Product depth**: Continue to invest in AI agents, global legal intelligence, and deeper integration into enterprise workflows (Slack, Salesforce, Word, Gmail). - **Move beyond task assistance to full automation**: The stated vision is to make legal “the last black box” in the enterprise — measurable, compressed, and owned internally. ## Why Work Here - **Culture & Philosophy**: Described as a team of “lawyers and engineers blending two worlds.” Core operating principles include: **“fewer, better people”** (small, elite teams), **relentless focus on simplicity**, and building products that are so elegant they “feel like magic.” The company explicitly values **judgment** as the key differentiator in an AI-powered world. - **Growth Trajectory**: A rare stage — Series B with $100M in funding, a small enough team that individual contributions matter every day, and early enough to shape how the company builds. Significant US expansion ahead. - **Work Environment**: Hybrid (roles listed for Edinburgh and London). The hiring process is transparent and values speed: a 30-min screening call, a 45-min technical interview, a short take-home challenge (a couple of hours), and a culture interview. - **Funding Backing**: Backed by the same investors who backed Figma, Stripe, and Canva — strong signal of ambition and long-term thinking. - **Impact**: Working on a problem that is “genuinely new” — building the platform to run in-house legal teams, which is a category that did not exist before AI made it possible. ## Sources 1. [wordsmith.ai](https://www.wordsmith.ai/) 2. [wordsmith.ai/company](https://www.wordsmith.ai/company) 3. [wordsmith.ai/careers](https://www.wordsmith.ai/careers) 4. [cbinsights.com](https://www.cbinsights.com/company/wordsmith-ai) 5. [jobs.ashbyhq.com/wordsmith](https://jobs.ashbyhq.com/wordsmith) ## Other roles at Wordsmith AI - [Sales Development Representative (SDR)](https://feeny.ai/job/sales-development-representative-sdr-wordsmith-ai-edinburgh-bvnwen75grd0) — Edinburgh, United Kingdom - [Legal Engineer (Privacy & Compliance)](https://feeny.ai/job/legal-engineer-privacy-compliance-wordsmith-ai-edinburgh-hxh477df6saa) — Edinburgh, United Kingdom - [Legal Solutions Engineer NYC](https://feeny.ai/job/legal-solutions-engineer-nyc-wordsmith-ai-new-york-q6hxkz1qvd1d) — New York, NY - [Account Executive - Enterprise - DACH](https://feeny.ai/job/account-executive-enterprise-dach-wordsmith-ai-munich-tq4cewds4x5e) — Munich, Germany - [Support Engineer](https://feeny.ai/job/support-engineer-wordsmith-ai-edinburgh-emw9xw5n5067) — Edinburgh, United Kingdom - [Product Manager](https://feeny.ai/job/product-manager-wordsmith-ai-edinburgh-12g19wwbk7he) — Edinburgh, United Kingdom - [Partner Manager](https://feeny.ai/job/partner-manager-wordsmith-ai-london-b2s7px7ykga8) — London, United Kingdom - [GRC Lead](https://feeny.ai/job/grc-lead-wordsmith-ai-edinburgh-9kzvttdajdy3) — Edinburgh, United Kingdom - [Data Scientist (Product Analytics)](https://feeny.ai/job/data-scientist-product-analytics-wordsmith-ai-edinburgh-g2h0m2yvsxxk) — Edinburgh, United Kingdom - [Strategic Partner Manager (Ecosystem & Frontier Alliances)](https://feeny.ai/job/strategic-partner-manager-ecosystem-frontier-alliances-wordsmith-ai-new-york-bwzbfysh1ewd) — New York, NY