Head of Sales Enablement

Head of Sales Enablement - NYC

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 organization 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

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.