GTM Strategy & Operations

Sales GTM Strategy & Planning

• Partner with Sales leadership and Finance to shape the GTM strategy for the Sales organization, including segmentation, territory design, coverage models, and rep engagement frameworks.
• Own complex, cross-functional strategic initiatives end-to-end: problem framing, business case, stakeholder alignment, execution, and post-launch measurement.
• Size opportunities and build data-driven investment cases that inform capacity planning, incentive design, and where Square directs Sales resources.

Performance & Productivity Insights

• Analyze Sales funnel data to diagnose performance gaps and surface initiatives that improve contact-to-close rates, deal velocity, and quota attainment.
• Partner with Analytics and Finance to define KPIs, stand up dashboards, and operate the WBR/MBR cadence that keeps Sales leadership close to the business.
• Translate complex analyses into rigorous performance narratives and actionable recommendations that inform leadership decisions.

Cross-Functional Execution & Program Management

• Lead cross-functional workstreams across Sales, Marketing, Product, Engineering, Analytics, and Finance, driving clarity, alignment, and structure through ambiguity.
• Translate business goals into clear technical requirements (PRDs/BRDs) and partner with technical teams to deliver programs on time and to spec.
• Break large, multi-quarter initiatives into pilots and iterations; manage the roadmap in collaboration with leadership and cross-functional partners.

AI, Automation & Process Innovation

• Identify and champion AI-native opportunities to increase Sales productivity across prospecting, lead scoring, deal support, and rep workflow automation.
• Partner with CRM, Systems, and Engineering on the design of process, policy, and system architecture, including routing, SLAs, rules of engagement, and handoffs.
• Stay at the frontier of AI-native GTM tooling and bring proven new approaches into the team's playbook.

Requirements

• 5+ years of experience in strategy and operations, revenue/sales operations, GTM strategy, business operations, or management consulting, ideally within SaaS, FinTech, or high-growth technology.
• A track record of owning complex, cross-functional strategic initiatives end-to-end — from problem framing through analysis, stakeholder alignment, execution, and measurement.
• Strong commercial instincts and comfort tying operational decisions to revenue outcomes, funnel health, and rep productivity.
• Comfort with ambiguity and a low-ego, ownership mindset: no task is too small, and you're motivated to build the operating system behind a world-class Sales organization.
• Excellent communication and stakeholder skills: you can influence senior partners without direct authority and keep cross-functional teams aligned through ambiguity.
• Hands-on experience with CRM, BI, and data warehouse tools (e.g., Salesforce, Looker, Snowflake, or equivalents) — able to pull data, translate it into insights, and make it useful for Sales leaders.