Director, GTM Strategy & Planning

About Us

Fivetran and dbt Labs are bringing together two industry-leading companies with a shared mission: helping organizations unlock the full value of their data. Together, we’re delivering the data infrastructure layer that helps organizations move, transform, and trust their data — from the moment data moves, through every transformation, to the context teams and AI systems rely on. Fivetran helps organizations automate data movement across the systems, clouds, engines, and tools they rely on. dbt Labs pioneered analytics engineering, helping teams transform data into reliable, governed insights. Together, we support thousands of organizations as they build a trusted foundation for analytics, AI, and better business decisions.

As we bring our teams and technology together, we’re building on the strengths of both companies while continuing to deliver the products and experiences our customers know and trust. It’s an exciting time to join us: we’re creating a company with the scale, talent, and technology to help more organizations put their data to work with greater speed, confidence, and impact. During this transition period, you may see references to both Fivetran and dbt Labs throughout our recruiting process as we integrate our teams, systems, and career sites.

About the Role

Fivetran is building data pipelines to power the modern data stack for thousands of companies. As we continue to scale globally, making the right strategic bets — on where to grow, how to structure our revenue teams, and how to allocate capacity — has never been more important.

We're looking for a Director, GTM Strategy & Planning to lead the team responsible for Fivetran's most consequential GTM decisions. You and your team will own GTM strategy and coverage model, market prioritization, revenue team segmentation, headcount planning, comp design principles, quota setting and territory design, and pipeline targets. You will also be a key partner with the Finance team on setting our annual financial plan across all regions and segments.

A defining opportunity for this leader is helping to align the go-to-market strategies of the combined Fivetran and dbt revenue organizations — building the frameworks and plans that bring two complementary sales teams together into a cohesive, high-performing GTM motion.

This role will partner closely with the CRO, CMO, GTM Strategy & Operations leadership, Finance, Analytics and sales leadership, and will require both the analytical depth to build rigorous frameworks and the executive presence to drive alignment on high-stakes decisions. You will lead a team of GTM strategy and planning professionals and be expected to develop them as well as elevate the function.

This is a full-time, hybrid position based out of our Oakland, Denver, Austin, or New York offices. Our hybrid work model offers a blend of remote flexibility and in-person collaboration, including two days in the office each week to connect and build as a team.

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

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