Senior Manager, GTM Strategy & Operations - Global Sales

About this role

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role:

As the Senior Manager, GTM Strategy & Operations, you'll be a strategic partner to senior Sales leadership and own the most consequential decisions shaping how Square's go-to-market organization is structured, prioritized, and scaled. You'll partner with senior leaders across GTM, Finance, Analytics, and Product/Engineering to translate company priorities into clear GTM direction and shape the bets that define Square's revenue trajectory.

This is a hands-on strategic role. You'll define the right questions, bring an independent point of view on where our GTM motion needs to evolve, and influence executive decisions through structured frameworks, financial rigor, and sharp written narrative. You'll also stay close to execution — building prototypes, owning complex cross-functional workstreams end-to-end, and raising the analytical bar across the team.

Your work will shape annual planning and investment strategy, the operating cadence of Sales leadership, the long-range design of Square's GTM motion across segmentation and coverage, and the executive narrative that aligns cross-functional partners around our most important bets. You will report to the Director of GTM Strategy & Operations, Global Sales, and will mentor junior members of the team.

You Will:

Sales GTM Strategy & Planning

• Serve as a thought partner to senior Sales and GTM executives, helping shape business priorities, resource allocation, and performance strategy.

• 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.

Performance & Business 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, build executive-ready dashboards, and own the WBR/MBR cadence that keeps Sales leadership close to the business.

• Translate complex analyses into executive-ready performance narratives and recommendations that drive leadership decisions and shape strategic bets.

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.

• Raise the AI-native operating bar across the GTM Strategy & Ops team — model what hands-on AI fluency looks like for other operators.

Team Leadership & Craft

• Mentor junior members of the GTM Strategy & Ops team; raise the bar on analytical rigor, written communication, and executive-ready output.

• Model the operating standards (ownership, bias to action, builder mindset) that define how the team works.

You Have:

• 8+ years of related experience with a Bachelor's degree; or 6 years and a Master's degree; or a PhD with 3 years experience; or equivalent experience in GTM Strategy, Sales Strategy, Revenue Operations, Business Operations, or Management Consulting — ideally within SaaS, FinTech, or high-growth technology.

• Proven track record of leading global, cross-functional strategic initiatives that drive measurable revenue, retention, or expansion outcomes.

• Demonstrated ability to influence executive-level stakeholders through structured analysis, clear narratives, and strong business judgment.

• Strong commercial instincts; comfort tying strategic decisions to investment prioritization and revenue outcomes.

• AI-native operating mindset: fluent with AI/LLMs in day-to-day work, hands-on with workflow automation, and energized by shipping real tools that remove manual work from the team.

• Expertise in CRM systems (e.g., Salesforce), GTM analytics tools (Looker,…