Director, GTM Strategy – Planning

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead and guide a team focused on GTM strategy, planning, and variable compensation; establish goals, oversee performance, and manage recruitment.

• Conduct comprehensive annual and in-year GTM planning cycles.

• Own and manage the integrated bottom-up pipeline model, aligning it with Finance's top-down forecast.

• Develop frameworks to assess new routes to market utilizing TAM/SAM analysis.

• Design and refine segmentation, coverage, and headcount models across enterprise, commercial, and self-service approaches.

• Assess cross-functional capacity plans across SE, CS, and PS.

• Direct quota establishment and territory design across various segments, including book-of-business allocations for expansion and customer teams.

• Supervise variable compensation planning and operations, encompassing incentive structures, payout modeling, and dispute management.

• Represent GTM Strategy within the Pricing Council and model revenue and attainment implications.

• Collaborate with field operations on QBR and executive presentation materials.

• Implement practical AI applications to enhance team productivity.

• Manage planning cycles, deliver capacity and coverage analyses, oversee variable compensation operations, and enhance quota attainment, capacity productivity, planning-cycle duration, and team capabilities.

⛳️ Requirements

• 10–12+ years of experience in GTM strategy, revenue operations, or management consulting in B2B SaaS or enterprise technology.

• At least 3 years of experience in managing and developing teams.

• Demonstrated success in leading comprehensive GTM planning, which includes quota design, territory allocation, TAM/SAM sizing, headcount capacity modeling, and large-scale sales segmentation.

• Direct experience managing variable compensation strategy and operations, including plan design, cost-of-sales modeling, dispute resolution, and payout execution.

• Experience navigating complex planning across mixed motions or managing significant organizational changes (preferred).

• Proficiency with contemporary revenue technology stacks, including Salesforce, incentive compensation tools like Everstage, CaptivateIQ, and Spiff, planning platforms such as Anaplan and Fullcast, and BI environments (preferred).

• Proven ability to leverage AI or automation workflows to optimize planning cycles and achieve measurable improvements in field productivity (preferred).

🏝️ Benefits

• Comprehensive BCBSIL medical, dental (high/low plans), and vision (Eyemed) insurance for you and your eligible dependents.

• Full, complimentary access to Modern Health for you and your dependents, which includes coaching, therapy sessions, and digital wellness resources.

• 401(k) plan with a 50% company match on your first 6% of contributions (totaling a 3% match).

• 100% employer-paid Life and Disability insurance.

• Flexible PTO policy.

• Additional company-wide Rest & Recharge days throughout the year.

• Up to 16 weeks of paid parental leave.

• $1,000 USD annual Lifestyle Spending Account.

• One-time $550 USD home office setup stipend.

• Monthly $50 USD internet stipend.

• 16 hours of paid volunteer time annually.

• $100 annual match for charitable donations.

• Pre-tax commuter benefits.

• Subsidized child and eldercare through Care.com.

• Discounted pet insurance through Figo.

• Complimentary personalized financial wellness support through Your Money Line.

• Flexible work location options where available in the United States.