GTM Enablement Manager (First Hire)

Overview

You're building OpenAI's GTM enablement function from scratch as the first hire on a new team. Your job is to take the constant flow of new models, product launches, and AI capabilities and turn them into clear guidance and training that helps the field sell more effectively. You'll work directly with the enablement lead, sales leadership, product teams, revops, and marketing to identify what matters and build programs to activate the GTM organization.

Role Snapshot

Company Context

Stage: Private / Late Stage (7,548 employees)

Size: ~7,500 employees

Growth: Rapid expansion mode with frequent product launches and model releases

Market Position: Category leader in AI - ChatGPT, GPT models, API platform, enterprise solutions. Product capabilities evolve faster than most companies' roadmaps.

GTM Reality

Your Stakeholders:

• Sales leadership (multiple segments - SMB, Mid-Market, Enterprise)
• Product teams shipping new capabilities constantly
• RevOps (systems, process, data)
• Marketing (positioning, messaging, campaigns)
• The field (AEs, SEs, CSMs who need to understand what changed and why it matters)

The Challenge: OpenAI moves extremely fast. New models drop, new features ship, new use cases emerge, competitive landscape shifts. Your job is to figure out what the field actually needs to know, cut through the noise, and deliver it in a way they can use in customer conversations.

Team Structure: You're hire #1 reporting to the enablement lead. You're building this from scratch - no existing programs, no established cadence, no playbooks. You define what good looks like.

What You'll Actually Do

Time Breakdown

Program Design (35%) | Stakeholder Alignment (30%) | Content Creation (25%) | Measurement (10%)

Key Activities

• Translating Product Launches: Product ships a new model or feature. You work with product and sales leadership to understand what's new, who cares, what objections it overcomes, and what changes in the sales conversation. Then you build the enablement (deck, talk track, demo guide, FAQ, whatever format makes sense).
• Building Training Programs: Design and deliver onboarding for new hires, ongoing training for existing reps on new capabilities, and certification programs. You're figuring out what format works - live sessions, async videos, self-serve modules, AI-native tools.
• Stakeholder Management: Lots of meetings with sales leaders, product managers, and other cross-functional partners. You're constantly negotiating priorities, getting feedback, and aligning on what enablement should focus on. Everyone has ideas about what the field needs to know.
• Creating Field Resources: Building sales plays, battle cards, competitive guides, discovery frameworks, demo scripts. You own making sure the field has what they need when a prospect asks a question or raises an objection.
• Measuring Impact: Figuring out if your programs actually work. Track completion rates, field adoption, deal velocity, win rates, and rep feedback. Most of this infrastructure doesn't exist yet - you'll build it.

The Honest Reality

What's Hard

• Pace is relentless: New product releases and model updates come fast. You'll be updating enablement materials constantly. Something you created last month might be partially obsolete.
• Competing priorities: Sales leadership wants rep training. Product wants field education on new features. RevOps wants process adoption. Marketing wants messaging reinforcement. You can't do everything - prioritization is constant.
• Unproven playbook: You're building this from scratch. There's no established way OpenAI does enablement. You'll experiment, some things won't work, and you'll iterate. Ambiguity is high.
• Measurement is tough: Connecting your enablement programs to revenue outcomes is hard. You'll get asked "did that training actually help close more deals?" and the answer is often fuzzy.
• Field skepticism: Reps are busy. They'll skip your training if it's not immediately useful. You need to prove value quickly or lose credibility.

What Success Looks Like

• Field adoption of your programs is high - reps actually use what you create
• Sales leaders request your support on key initiatives because they trust your work
• You've built repeatable frameworks (onboarding, launch enablement, ongoing training) that scale
• Reps can clearly articulate new product capabilities and competitive positioning after your training
• You've established metrics that tie enablement to business outcomes

Who You're Enabling

Primary Audience:

• Account Executives (selling to startups, mid-market, enterprise)
• Sales Engineers (running technical demos and POCs)
• Customer Success Managers (driving adoption and expansion)
• Sales Development Reps (qualifying and booking meetings)

What They Need:

• Clarity on what changed and why it matters to their deals
• Talk tracks and demo guidance for new capabilities
• Competitive intelligence and objection handling
• Onboarding that gets them productive fast
• Just-in-time resources when they're in a deal

Requirements

• 5+ years in sales enablement, ideally at a fast-growth B2B SaaS company
• Experience building enablement programs from scratch or in high-ambiguity environments
• Strong understanding of enterprise sales motions - you've been close enough to deals to know what reps actually need
• Program design skills - you can take a messy problem, define the right solution, and execute it
• Excellent communication and stakeholder management - you'll be working across a lot of teams with competing priorities
• Comfortable with AI and technical products - you need to understand OpenAI's capabilities well enough to explain them clearly
• Self-directed and resourceful - there's no playbook, you figure things out
• Experience with enablement tools and LMS platforms is helpful but not required