Director of GTM Strategy & Planning, Fivetran

• 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

Desirable

• 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
• 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