Head of GTM Enablement

About Lightfield

Lightfield is reimagining CRM as a world model of a business. By learning from emails, meetings, and customer conversations, we’re building a living understanding of how a company works—so AI can help teams anticipate what comes next, make better decisions, and take action.

More than 5,000 companies have used the product since its November launch. We’ve raised more than $70M from Andreessen Horowitz, Coatue, Maverick Ventures, and Greylock to attack the biggest software category in the world. We previously built Tome, which reached more than 25 million users, and our team brings experience from Llama, Instagram, Google, and Salesforce.

The Role

We’re looking for a Head of GTM Enablement to build the programs, systems, and AI-powered workflows that help our sales team ramp faster, sell more effectively, and continuously improve.

This isn’t a traditional enablement role focused on training sessions and content management. You’ll combine sales expertise, strategic thinking, and a builder’s mindset to create an AI-native enablement function that scales as we grow.

You’ll work closely with Sales leadership, Product, and Engineering to turn what our best sellers do into repeatable processes and build a team that gets better with every customer interaction.

What You’ll Do

• Own onboarding and ramp: Build scalable onboarding programs, certifications, and learning experiences that get new reps productive quickly.

• Drive sales effectiveness: Identify skill gaps through performance data and real customer conversations, and deliver targeted coaching on discovery, qualification, value selling, competitive positioning, and deal execution.

• Build AI-native enablement: Use AI agents, skills, and automations to deliver personalized coaching, call analysis, meeting preparation, and just-in-time guidance directly into seller workflows.

• Develop our sales playbook: Partner with Sales leadership to define and continuously improve our sales methodology, processes, messaging, and best practices across high-velocity and strategic sales.

• Enable complex selling: Equip sellers to navigate technical evaluations, POCs, executive conversations, and multi-stakeholder deals with greater independence.

• Measure impact: Own enablement effectiveness through ramp time, conversion rates, win rates, and seller productivity, continuously improving programs based on results.

What You’ll Bring

• 5+ years in Sales Enablement, Sales Leadership, or Sales Coaching, ideally at a high-growth B2B SaaS company.

• Strong understanding of modern B2B sales methodologies, with experience improving sales execution and performance.

• Deep enthusiasm for AI and hands-on experience building AI-powered workflows, agents, or automations. You see AI as a way to fundamentally rethink enablement, not just create content faster.

• A strategic, analytical mindset with the ability to diagnose performance gaps and translate insights into effective coaching and systems.

• Strong facilitation and coaching skills, with credibility among experienced sellers and sales leaders.

• A builder’s mentality and comfort operating hands-on in a fast-moving, early-stage environment.

Benefits & Perks

• Competitive salary

• Meaningful early equity

• Health insurance (medical, dental, vision)

• 3 weeks of PTO

• 11 paid company holidays + we enjoy a winter holiday break

• 3 months of paid family leave

• Wednesdays work from home

• Regular team dinners, events, offsites, and retreats

• 401k plan

• Other perks include: commuter and lunch stipend