GTM Planning Operations

Overview

You're the person building the operational foundation that determines how OpenAI's sales org is structured, what quotas look like, and who sells to whom. You work in Excel and planning tools most of the day, partnering with GTM leadership and finance to turn revenue goals into workable territory plans and quota allocations. This isn't CRM admin work—you're making strategic decisions about how to carve up the market.

Role Snapshot

Company Context

Stage: Growth/Scale-up (funded by Microsoft, operating at scale post-ChatGPT launch)

Size: ~7,460 employees

Growth: Aggressive GTM expansion—OpenAI went from research org to commercial product company in under 2 years. They're scaling enterprise sales, partnerships, and API distribution simultaneously.

Market Position: Category creator in generative AI. Every enterprise wants to talk to them, but they're still figuring out how to commercialize at scale.

GTM Reality

OpenAI's GTM motion is evolving rapidly:

Pipeline Sources:

• High inbound volume from ChatGPT brand recognition and product-led signups
• Enterprise teams doing outbound to Fortune 500 for API/Azure OpenAI Service deals
• Partnership-driven motion through Microsoft and cloud marketplaces

Team Structure: Mix of enterprise AEs, mid-market teams, partnership managers, and technical account managers. The org is hiring aggressively and the structure keeps changing.

Your Challenge: You're designing planning systems for an org that's growing 50%+ and shifting strategy quarterly. What works in Q1 might be obsolete by Q3.

What You'll Actually Do

Time Breakdown

Analysis/Modeling (40%) | Stakeholder Meetings (35%) | Documentation/Process (25%)

Key Activities

• Quota Setting & Allocation: Build models to break down company revenue targets into territory-level quotas. You're pulling historical data, factoring in market potential, and defending your math to sales leaders who want more achievable numbers. Expect multiple rounds of revision.

• Territory & Segmentation Design: Define account assignment rules—who owns what customer based on size, industry, geography. You're making trade-off decisions: Should SMB accounts go to inside sales or partners? Where's the cutoff between mid-market and enterprise? These decisions affect people's comp, so they're political.

• Coverage Model Planning: Determine rep-to-account ratios, span of control for managers, when to split territories. You're answering: Do we need more AEs or more SDRs? Should we add an overlay team for a specific industry? Your recommendations drive headcount planning.

• Cross-Functional Alignment: Constant syncs with finance (revenue forecasting), sales leadership (feasibility checks), HR (hiring plans), and systems teams (CRM implementation). You're translating between different stakeholder languages and getting everyone to agree on one version of truth.

The Honest Reality

What's Hard

• Moving Target: OpenAI's strategy is evolving. The segmentation you design in Q1 might need to be redrawn in Q2 because they've launched a new product or changed their enterprise focus. You need to be comfortable with continuous iteration.

• High-Stakes Politics: Quota and territory decisions directly affect people's paychecks. Sales leaders will push back on your models. Reps will argue their territories are harder. You're constantly defending your methodology and managing stakeholder expectations.

• Ambiguity and Imperfect Data: The company is growing so fast that historical data is limited. You're building models with incomplete information and making educated guesses. If you need perfect data to feel confident, this will be stressful.

• Senior Stakeholder Management: You're presenting to VPs and potentially C-level. They're smart, they're busy, and they expect you to have thought through all the edge cases. The scrutiny is high.

What Success Looks Like

• Sales leadership trusts your models and uses them for decision-making without constantly questioning the methodology
• Quota attainment across the org is 60-80% (shows quotas are challenging but achievable, not sandbags or pipe dreams)
• Territory transitions and reorgs happen smoothly without mass complaints or comp disputes
• You can quickly model different scenarios when leadership asks "what if we changed X?"

Who You're Working With

Internal Partners:

• GTM leadership (VPs of Sales, Revenue, Partnerships)
• Finance/FP&A (for revenue planning and forecasting alignment)
• Sales ops and systems teams (to implement your designs in CRM)
• Enablement (to communicate changes to the field)

What They Care About:

• Sales Leaders: Want quotas that are ambitious but achievable. Don't want their teams demoralized by impossible targets or confused by messy territories.
• Finance: Need your plans to roll up to company revenue targets. Want clean data and audit trails.
• Individual Reps: Care about fair account distribution and quotas that give them a real shot at making money.

Requirements

• 3-5+ years in sales operations, revenue operations, or GTM planning (ideally at a high-growth tech company)
• Advanced Excel/Google Sheets skills—pivot tables, lookups, scenario modeling are table stakes
• Experience with BI tools (Tableau, Looker, or similar) for analysis and dashboards
• Comfort with ambiguity and rapid change—you can't wait for perfect information
• Stakeholder management skills—you'll be defending your work to senior leaders who will poke holes in it
• Analytical rigor and attention to detail—small errors in your models cascade into big compensation or coverage problems
• Bonus: Familiarity with Salesforce or other CRM platforms, knowledge of different GTM motions (enterprise, mid-market, PLG)