CareerPlan

Director, GTM Strategy & Planning

Chicago OfficeFull-time2026-09-10 → 2026-11-10

Core

Lead the team building plans for how the revenue organization is structured, sized, and targeted, including GTM strategy, planning, and variable compensation.

Role type

Director, GTM Strategy & Planning

Builds

Integrated bottom-up pipeline models, segmentation/coverage/headcount models, quota designs, territory plans, and variable compensation structures.

Domain

B2B SaaS / Enterprise Tech

Required skills

GTM strategy, revenue operations, team leadership, quota design, territory planning, variable compensation design, TAM/SAM analysis, capacity modeling, sales segmentation

Preferred skills

Mixed motion planning (enterprise, PLG, partner, self-service), organizational reorganization experience, modern revenue tech stacks, AI/automation workflows

Technologies

Salesforce, Everstage, CaptivateIQ, Spiff, Anaplan, Fullcast

Responsibilities

Lead and mentor a team spanning GTM strategy, planning, and variable compensation; Run end-to-end annual and in-year GTM planning cycles; Design and optimize segmentation, coverage, and headcount models; Lead equitable quota setting and territory design; Oversee variable comp planning and operations; Serve as GTM Strategy representative on the Pricing Council

Seniority

Director, hands-on IC with team management