# Director, GTM Strategy & Planning

**Company:** [Fivetran](https://hotfix.jobs/companies/fivetran)
**Location:** Unspecified
**Role:** GTM Engineering
**Salary:** $169k – $211k/yr
**Experience:** 10+ years
**Skills:** Go-to-Market Strategy, Revenue Strategy, Quota Setting, Territory Planning, Headcount Planning, Tam Analysis, Sales Compensation Design, Market Segmentation, Pipeline Modeling, Financial Modeling, B2B Saas Go-To-Market, Management Consulting
**Posted:** 2026-07-02

> Lead the GTM Strategy & Planning team to drive Fivetran's annual planning, headcount models, quota/territory design, market prioritization, and pipeline targets. Partner with CRO, Finance, and leadership on strategic decisions, coverage models, and post-merger GTM alignment for the combined Fivetran/dbt revenue organizations. Requires 10+ years in revenue/GTM strategy with 4+ years managing teams.

## Job Description

## What You’ll Do

- Lead, develop, and grow a team of GTM strategy and planning professionals, fostering a high-performance culture grounded in Fivetran's core values
- Drive the annual and ongoing GTM planning cycle in close partnership with the CRO, CMO, GTM Strategy & Operations, GTM Analytics, and Finance — translating business objectives into an integrated plan across the revenue organization and holding the process accountable to key milestones and decisions
- Own the annual and in-year headcount planning process for the revenue organization, partnering with Finance and People to translate strategic priorities into capacity models
- Design and execute the global quota-setting and territory planning process, including book-of-business cuts for existing customer and expansion segments, with a commitment to equitable opportunity distribution and revenue maximization
- Drive key strategic decisions across the revenue organization, including market segmentation, revenue team structure, and coverage model design
- Own the bottom-up pipeline model and targets across all GTM teams (Sales, Partners, Business Development, Marketing) and partner with Finance on a top-down analytical forecast model — together providing an integrated view of revenue growth potential
- Partner with Sales, Marketing, and Product to identify and prioritize high-impact sales plays and optimize persona targeting, ensuring the revenue team is focused on the highest-value buyer profiles and translating strategic insights into actionable revenue motions
- Evaluate market entry opportunities and develop geography-specific GTM strategies — using TAM analysis and feasibility frameworks to prioritize expansion and adapting approaches for local market dynamics, competitive landscape, and go-to-market maturity
- Develop and maintain the partner GTM strategy in collaboration with alliances and channel leadership, ensuring the partner motion — and the marketing plan and targets — are integrated with the broader GTM plan
- Identify where AI can materially improve GTM productivity and lead cross-functional efforts to prioritize and implement the highest-impact use cases
- Partner with field operations to lead the preparation of GTM performance materials for key executive forums, including QBRs and Board meetings
- Advise revenue, Finance, and HR leadership on sales compensation structure design, providing analysis and recommendations on how plan mechanics drive or inhibit desired seller behaviors
- Build the strategic planning frameworks, models, and deliverables that enable data-driven decision-making at the executive level, and serve as the CRO and sales leadership's primary thought partner on annual planning, mid-year resets, and evolving strategic priorities

## Skills We’re Looking For

- 10+ years of experience in sales strategy, revenue strategy, GTM strategy, or management consulting in a B2B SaaS or enterprise technology environment
- 4+ years of experience managing and developing a team, with a track record of building high-functioning strategy functions
- Demonstrated experience owning quota design, territory planning, and headcount modeling at scale — you've done this, not just advised on it
- Strong analytical skills and financial acumen; comfortable building and pressure-testing complex models and translating outputs into clear strategic direction
- Deep knowledge of B2B SaaS go-to-market models in a consumption-based business, including segmentation frameworks, coverage design, and sales motion optimization
- Experience advising on or designing sales compensation structures with an understanding of how incentive mechanics drive behavior
- Experience leading GTM alignment across merged, acquired, or rapidly reorganized sales organizations
- Proven ability to operate at the executive level — synthesizing complexity, influencing without authority, and driving alignment among senior stakeholders
- Experience with market sizing, TAM/SAM analysis, and market entry prioritization frameworks
- Clear, concise communicator who can present rigorous work simply and credibly to a broad audience

## Bonus Skills

- Experience in the data infrastructure, analytics, or adjacent technology categories
- Background in management consulting (McKinsey, Bain, BCG, or equivalent)
- Experience scaling a GTM strategy function through a period of rapid organizational growth

## Similar roles

- [Director, Go-To-Market (GTM)](https://hotfix.jobs/jobs/105f727e-8aac-47fc-a31d-459cc234ce38) - Regal.ai - New York, NY - $170k – $250k/yr
- [Director, Ad Platform Strategy, Go-To-Market](https://hotfix.jobs/jobs/5904770a-00da-431b-b9a8-d2b1c59213f0) - Fetch - Remote - $174k – $205k/yr
- [Director, Technical GTM](https://hotfix.jobs/jobs/6f5b7ff7-9234-4905-bb10-ea4cc22ebbcc) - Narmi - Remote - $175k – $200k/yr
- [Director, GTM Engineering](https://hotfix.jobs/jobs/5598a1e3-f28d-471b-aec7-e19cdbbd8b15) - 1Password - Remote - $200k – $300k/yr
- [Head of GTM Systems and Engineering](https://hotfix.jobs/jobs/3c7ab426-b091-470f-be3e-2127dcc11fe5) - Applecart - New York, NY - $200k – $230k/yr

**Apply:** https://hotfix.jobs/jobs/e617336b-210b-44e0-8201-07c91fae0ce0
**Canonical:** https://hotfix.jobs/jobs/e617336b-210b-44e0-8201-07c91fae0ce0